o-Phthalaldehyde = OPA
CAS Number: 643-79-8
EC Number: 211-402-2
Chemical formula: C8H6O2
Molar mass: 134.134 g·mol−1
Phthalaldehyde (sometimes also o-phthalaldehyde or ortho-phthalaldehyde, OPA) is the chemical compound with the formula C6H4(CHO)2.
o-Phthalaldehyde is one of three isomers of benzene dicarbaldehyde, related to phthalic acid.
o-Phthalaldehyde is a building block in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids.
o-Phthalaldehyde dissolves in water solution at pH < 11.5.
o-Phthalaldehydes solutions degrade upon UV illumination and exposure to air.
o-Phthalaldehyde, Reagent is a reagent in the analysis of amino acids and involved in the synthesis of heterocyclic compounds.
A reagent that forms fluorescent conjugation products with primary amines.
o-Phthalaldehyde is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.
Phthalaldehyde, also o-phthalaldehyde or ortho-phthalaldehyde or OPA, is the chemical compound with the formula C6H4(CHO)2.
o-Phthalaldehyde is one of three isomers of benzene dicarbaldehyde.
o-Phthalaldehyde is commonly used as a high-level disinfectant for medical instruments, as a polymerizer as well as in certain methods of wine making.
o-Phthalaldehyde is the chemical compound with the formula C6H4(CHO)2.
Often abbreviated OPA, the molecule is a dialdehyde, consisting of two formyl (CHO) groups attached to adjacent carbon centres on a benzene ring.
This pale yellow solid is a building block in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids.
o-Phthalaldehyde (OPA) is a chemical reagent that forms fluorescent conjugation products with primary amines.
o-Phthalaldehyde is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.
o-Phthalaldehyde is approved by FDA for use in test systems to detect blood urea nitrogen (BUN) for the diagnosis and treatment of certain renal and metabolic diseases.
o-Phthalaldehyde is also a known desinfectant and has been approved for high-level sterilization of heat-sensitive medical instruments and is increasingly being used as a replacement in the healthcare industry for glutaraldehyde.
o-Phthalaldehyde has also been approved for use as an indoor antimicrobial pesticide; an intermediate for the synthesis of pharmaceuticals, medicines, and other organic compounds.
ChEBI: A dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.
Peptide modification methods that do not rely on the cysteine residue are underdeveloped, and their development could greatly expand the current toolbox for peptide chemistry.
During the course of preliminary investigations into the classical ortho-phthalaldehyde (o-Phthalaldehyde)-amine-thiol condensation reaction, we found that in the absence of thiol, o-Phthalaldehyde readily condenses with two primary alkyl amines to form a class of underexplored isoindolin-1-imine compounds under mild aqueous conditions.
From the intramolecular version of this o-Phthalaldehyde - 2amines reaction, an efficient and selective methodology using mild reaction conditions has been developed for stapling unprotected peptides via crosslinking of two amino groups in both an end-to-side and side-to-side fashion.
The stapling method is superfast and broadly applicable for various peptide substrates with the reacting amino groups separated by a wide range of different amino acid units.
The macrocyclization reactions of selected substrates are completed within 10 seconds at 5 mM concentration and within 2 minutes at 50 μM concentration.
Importantly, the resulting cyclized peptides with an isoindolinimine linkage can be extended in a one-pot sequential addition manner with several different electron-deficient π electrophiles, thereby generating more complex structures.
Highly differentiated epidermis tissue derived from normal, human-derived epidermal keratinocytes, were used to determine the skin irritation potential of o-Phthalaldehyde and glutaraldehyde.
Treatment with 0.4125% and 0.55% o-Phthalaldehyde induced irritation, while glutaraldehyde exposure at these concentrations did not.
The invention provides test paper for testing the concentration of an o-Phthalaldehyde disinfectant.
The test paper comprises a base plate and a reaction cushion pasted on the base plate, wherein the reaction cushion is obtained by drying filter paper which is dipped in a sulfite solution and a pH mixing indicating agent solution; when the content of ortho-phthalaldehyde is greater than the minimum effective concentration, the pH value of a reaction product completely exceeds the color change point of the mixing indicating agent, the test paper reaction cushion is completely changed into blue purple from yellow, and the higher the concentration of o-Phthalaldehyde is, the darker the blue purple color on the test paper reaction cushion is.
The test paper is rapid and flexible in reaction, is short in color developing time, can be taken out when being dipped into the ortho-phthalaldehyde disinfectant for one second, can analyze the testing result in one minute by referring to a color chart of an operation instruction, is simple, convenient and rapid to use, and is conveniently used for detecting medical instruments, such as an endoscope in the disinfection process any time by medical staff in a hospital.
o-Phthalaldehyde is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 to < 100 tonnes per annum.
o-Phthalaldehyde is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Biocides generally have multiple biochemical targets.
Such a feature easily entangles the analysis of the mechanisms of antimicrobial action.
In this study, the action of the dialdehyde biocide ortho -phtalaldehyde (o-Phthalaldehyde), on bacteria, was investigated using the Gram-negative Pseudomonas fluorescens.
The targets of the biocide action were studied using different bacterial physiological indices.
The respiratory activity, membrane permeabilization, physico-chemical characterization of the bacterial surfaces, outer membrane proteins (OMP) expression, concomitant influence of pH, contact time and presence of bovine serum albumin (BSA) on respiratory activity, morphological changes and o-Phthalaldehyde-DNA interactions were assessed for different OPA concentrations.
With the process conditions used, the minimum inhibitory concentration was 1500 mg/l, the concentration to promote total loss of bacterial culturability was 65 mg/l and the concentration needed to inactivate respiratory activity was 80 mg/l.
These data are evidence that culturability and respiratory activity were markedly affected by the biocide.
o-Phthalaldehyde lead, moreover, to a significant change in cell surface hydrophobicity and induced propidium iodide uptake.
Such results suggest cytoplasmic membrane damage, although no release of ATP was detected.
At pH 5, the bactericidal action of o-Phthalaldehyde was stronger, though not influenced by BSA presence.
Nevertheless, at pH 9, BSA noticeably (p < 0.05) impaired biocide action.
A time-dependent effect in o-Phthalaldehyde action was evident when contemplating respiratory activity variation, mainly for the lower exposure times.
Scanning electron microscopy allowed to detect bacterial morphological changes, translated on cellular elongation, for o-Phthalaldehyde concentrations higher than 100 mg/l.
Interferences at DNA level were, however, restricted to extreme biocide concentrations.
The overall bactericidal events occurred without detectable OMP expression changes.
In conclusion, the results indicated a sequence of events responsible for the antimicrobial action of o-Phthalaldehyde: it binds to membrane receptors due to cross-linkage; impairs the membrane functions allowing the biocide to enter through the permeabilized membrane; it interacts with intracellular reactive molecules, such as RNA, compromising the growth cycle of the cells and, at last, with DNA.
End-capped poly(phthalaldehyde) (PPA) synthesized by anionic polymerization has garnered significant interest due to its ease of synthesis and rapid depolymerization.
However, alternative ionic polymerizations to produce PPA have been largely unexplored.
In this report, we demonstrate that a cationic polymerization of o-phthalaldehyde initiated by boron trifluoride results in cyclic PPA in high yield, with high molecular weight, and with extremely high cyclic purity.
The cyclic structure is confirmed by NMR spectroscopy, MALDI-TOF mass spectrometry, and triple-detection GPC.
The cyclic polymers are reversibly opened and closed under the polymerization conditions.
Owing to PPA’s low ceiling temperature, cyclic PPA is capable of chain extension to larger molecular weights, controlled depolymerization to smaller molecular weights, or dynamic intermixing with other polymer chains, both cyclics and end-capped linears.
These unusual properties endow the system with great flexibility in the synthesis and isolation of pure cyclic polymers of high molecular weight.
Further, we speculate that the absence of end groups enhances the stability of cyclic PPA and makes it an attractive candidate for lithographic applications.
o-Phthalaldehyde is a dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.
o-Phthalaldehyde has a role as an epitope.
o-Phthalaldehyde is a dialdehyde and a member of benzaldehydes.
Thermo Scientific Pierce Fluoraldehyde o-Phthalaldehyde Reagent is a ready-to-use solution of o-phthalaldehyde, a fluorescent derivatization reagent for peptide or amino acid detection and quantitation in HPLC.
Fluoraldehyde Reagent Solution contains OPA (o-phthalaldehyde), which reacts with primary amines of amino acids, peptide and proteins to enable fluorescent detection and quantitation.
The reagent that can be used as a protein or peptide assay reagent or as a pre- or post-column detection reagent for amino acid analysis (HPLC).
Reaction of OPA with proteins and peptides yields linear results over a wide range of concentrations.
The Fluoraldehyde Reagent Solution is supplied ready to use and enables fast quantitation of proteins or peptides in solution.
Fast and catalyst-free cross-linking strategy is of great significance for construction of covalently cross-linked hydrogels.
Here, we report the condensation reaction between o-phthalaldehyde (OPA) and N-nucleophiles (primary amine, hydrazide and aminooxy) for hydrogel formation for the first time.
When four-arm poly(ethylene glycol) (4aPEG) capped with o-Phthalaldehyde was mixed with various N-nucleophile-terminated 4aPEG as building blocks, hydrogels were formed with superfast gelation rate, higher mechanical strength and markedly lower critical gelation concentrations, compared to benzaldehyde-based counterparts. Small molecule model reactions indicate the key to these cross-links is the fast formation of heterocycle phthalimidine product or isoindole (bis)hemiaminal intermediates, depending on the N-nucleophiles.
The second-order rate constant for the formation of phthalimidine linkage (4.3 M−1 s−1) is over 3000 times and 200 times higher than those for acylhydrazone and oxime formation from benzaldehyde, respectively, and comparable to many cycloaddition click reactions.
Based on the versatile OPA chemistry, various hydrogels can be readily prepared from naturally derived polysaccharides, proteins or synthetic polymers without complicated chemical modification.
Moreover, biofunctionalit is facilely imparted to the hydrogels by introducing amine-bearing peptides via the reaction between OPA and amino group.
o-Phthalaldehyde is used in precolumn derivatization of amino acids for HPLC separation.
o-Phthalaldehyde is also used for flow cytometric measurements of protein thiol groups.
A reagent that forms fluorescent conjugation products with primary amines.
Phthalaldehyde is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.
o-Phthalaldehyde can be polymerized.
In the polymer, one of the oxygen atoms forms a bridge to the other non-ring carbon of the same o-Phthalaldehyde unit, while the other bridges to a non-ring carbon of another phthalaldehyde unit.
Poly(phthalaldehyde) is used in making a photoresist.
A simple, rapid technique has been developed for the visualization of histamine in its cellular depots throughout the body.
Based on the yellow fluorochrome formed by the interaction of o-phthalaldehyde and histamine, this procedure permits direct fluorescence microscopy of the "histaminocytes."
Study of fresh blood and tissues from man and many animals revealed histamine its the mast cells, blood vessels, gastric mucosa, and in some species, platelets.
The molecule was first described in 1887 when it was prepared from α,α,α',α’-tetrachloro-ortho-xylene.
A more modern synthesis is similar: the hydrolysis of the related tetrabromoxylene using potassium oxalate, followed by purification by steam distillation.
The reactivity of OPA is complicated by the fact that with water it forms both a mono- and dihydrate, C6H4(CHO)(CH2OH) and C6H4(CH2OH)2, respectively.
Disinfection of o-Phthalaldehyde:
OPA is commonly used as a high-level disinfectant for medical instruments, commonly sold under the brand names of Cidex OPA or TD-8.
Disinfection with o-Phthalaldehyde is indicated for semi-critical instruments that come into contact with mucous membranes or broken skin, such as specula, laryngeal mirrors, and internal ultrasound probes.
Keywords of o-Phthalaldehyde:
Superfast gelation
o-phthalaldehyde chemistry
Versatile cross-linking
Functional hydrogel
Reaction kinetics
o-Phthalaldehyde is a building block in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids.
KEYWORDS:
643-79-8, 211-402-2, OPA, 1 2-BENZENEDICARBALDEHYDE, OPTA, NSC 13394, UNII-4P8QP9768A, CHEBI:70851, 2-PHTHALDIALDEHYDE, MFCD00003335
Synthesis and reactions of o-Phthalaldehyde:
The compound was first described in 1887 when it was prepared from α,α,α’,α’-tetrachloro-ortho-xylene.
A more modern synthesis is similar: the hydrolysis of the related tetrabromo-o-xylene using potassium oxalate, followed by purification by steam distillation.
The reactivity of o-Phthalaldehyde is complicated by the fact that in water it forms both a mono- and dihydrate, C6H4(CHO)(CH(OH)2) and C6H4(CH(OH))2O, respectively.
Phthalaldehydes reactions with nucleophiles often involves the reaction of both carbonyl groups.
o-Phthalaldehyde is mainly used as a high-level disinfectant (a low-temperature chemical method) for heat-sensitive medical and dental equipment such as endoscopes and thermometers; in recent years, it has gained popularity as a safe and better alternative to glutaraldehyde.
There are some researches show, pH7.5 contains the sterilizing agent of o-phthalaldehyde 0.5%, and its sterilizing power, sterilization speed, stability and toxicity all are better than glutaraldehyde, can kill mycobacterium in the 5min, the bacterium number reduces by 5 logarithmic value, and o-phthalaldehyde is very stable, tasteless in pH3～9 scopes, non-stimulated to human nose, eye mucosa, and need not activate before using, various materials are had good consistency, have tangible microbiocidal activity.
The reactivity of o-Phthalaldehyde is complicated by the fact that in water it forms both a mono- and dihydrate, C6H4(CHO)(CH(OH)2) and C6H4(CH(OH))2O, respectively. Its reactions with nucleophiles often involves the reaction of both carbonyl groups.[
Preparation of o-Phthalaldehyde:
o-Phthalaldehyde is a high-level chemical disinfectant that is commonly used for disinfection of dental and medical instruments as an alternative to glutaraldehyde, which is a known skin and respiratory sensitizer.
A variety of processes for manufacturing o-phthalaldehyde have been reported in the literature.
o-Phthalaldehyde is produced by heating pure benzaldehyde and chloroform with potassium hydroxide solution.
The resulting solution is further acidified with hydrochloric acid and cooled to yield a colorless powder of o-phthalaldehyde.
o-Phthalaldehyde is also produced by ozonization of naphthalene in alcohol followed by catalytic hydrogenation.
Catalytic oxidation of various chemicals is also used in manufacturing o-phthalaldehyde.
o-Phthalaldehyde can be manufactured by oxidation of phthalan by nitrogen monoxide in acetonitrile with N-hydroxyphthalimide as the catalyst to yield 80% to 90%.
Biochemistry of o-Phthalaldehyde:
o-Phthalaldehyde is used in a very sensitive fluorescent reagent for assaying amines or sulfhydryls in solution, notably contained in proteins, peptides, and amino acids, by capillary electrophoresis and chromatography.
o-Phthalaldehyde reacts specifically with primary amines above their isoelectric point Pi in presence of thiols.
o-Phthalaldehyde reacts also with thiols in presence of an amine such as n-propylamine or 2-aminoethanol.
The method is spectrometric (fluorescent emission at 436-475 nm (max 455 nm) with excitation at 330-390 nm (max. 340 nm)).
Specifications of o-Phthalaldehyde:
Label or Dye: OPA (o-phthaldialdehyde)
Quantity: 945 mL
Format: Liquid
Product Type: o-Phthaldialdehyde Reagent Solution
Chemical Reactivity: Amine
Product Line: Fluoraldehyde
Alternate Names: 2-Carboxybenzaldehyde; Phthaldialdehyde; o-Phthalic dicarboxaldehyde; Benzene-1,2-dicarboxaldehyde; OPA
Application Notes: o-Phthalaldehyde is used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups. Used for fluorometric determination of histamine, histidine and other amino acids. Also used for cholesterol assay in the picomole range.
Base Catalog Number: 102648
Beilstein Registry Number: 878317
CAS #: 643-79-8
EC Number: 211-402-2
Format: Crystals
Hazard Statements: H301-H314-H317-H400
Molecular Formula: C8H6O2
Molecular Weight: 134.134 g/mol
Personal Protective Equipment: Faceshields, full-face respirator, Gloves, Goggles, respirator filter
Purity: ≥98%
RTECS Number: TH6950000
Safety Symbol: GHS05, GHS06, GHS09
Appearance: Light yellow to Yellow to Green powder to crystal
Purity(GC): min. 99.0 %
Melting point: 55.0 to 58.0 °C
Applications of o-Phthalaldehyde:
1. Analytical reagents in the chemical field : As an amine alkaloid reagent, o-Phthalaldehyde is used for the determination of primary amines and peptide bond decomposition products by fluorescence method.
2. Organic synthesis : also a pharmaceutical intermediate.
3. A fluorescent reagent for separating amino acid derivatives by HPLC before column chromatography, and measuring thiol groups of proteins by flow cytometry.
o-Phthalaldehyde (OPA) is used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups.
o-Phthalaldehyde is used for fluorometric determination of histamine, histidine and other amino acids.
o-Phthalaldehyde is also used for cholesterol assay in the picomole range.
o-Phthalaldehyde is a compound that reacts with primary amines to produce a product that emits a highly fluorescent blue colour.
o-Phthalaldehyde is used for the quick visualization of histamine, characterized by the appearance of a yellow stain.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
Typical Procedure: 5-10 µL aliquots of amino acid standards or unknown samples are mixed with 5 µL of a solution prepared by dissolving of o-phthalaldehyde (50 mg) in absolute MeOH (1.25 mL) followed by the addition of 2-mercaptoethanol (50 µL) and 0.4 M sodium borate (pH 9.5) (11.2 mL).
After 1 min, 0.1 M sodium acetate (pH 7.0) (20-100 µL) are added, the solution mixed and a 20-µL sample is subjected to analysis.
O-Phthalaldehyde, in the presence of 2-mercaptoethanol, reacts with primary amines to form highly fluorescent products.
Picomole quantities of amino acids, peptides, and proteins can be detected easily.
o-Phthalaldehyde is five to ten times more sensitive than fluorescamine and is soluble and stable in aqueous buffers.
o-Phthalaldehyde has been used:
in the preparation of reagent for determining the degree of hydrolysis of milk proteins
in the measurement of free amino acids of milk samples by O-phthaldialdehyde/N-acetyl-L-cysteine (OPA/NAC) assay
in the derivatization of putrescine samples
For precolumn derivatization of amino acids for HPLC separation.
For flow cytometric measurements of protein thiol groups.
o-Phthalaldehyde is a compound used in precolumn derivatization of amino acids for HPLC separation
Potential Exposure of o-Phthalaldehyde:
The primary routes of human exposure to o-phthalaldehyde are by inhalation and through the skin, which may occur through accidental or occupational exposures.
Along with its increasing popularity as a chemical sterilizer, o-phthalaldehyde has many applications in analytical methods and in diagnostic kits.
o-Phthalaldehyde is also used as an intermediate in the synthesis of pharmaceuticals and as a reagent in the tanning industry, hair colorings, wood treatment, and antifouling paints.
o-Phthalaldehyde was approved for use as an indoor antimicrobial pesticide in 1997; however, it is no longer registered with the United States Environmental Protection Agency (USEPA) for this use.
Storage and Packing of o-Phthalaldehyde:
Well closed.
Separated from oxidants, amines, strong bases and food and feedstuffs.
Ventilation along the floor.
Store o-Phthalaldehyde in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
o-Phthalaldehyde is used in the following products: biocides (e.g. disinfectants, pest control products), laboratory chemicals and washing & cleaning products.
Release to the environment of this substance can occur from industrial use: formulation of mixtures.
Do not transport with food and feedstuffs.
Marine pollutant.
Safety of o-Phthalaldehyde:
Flash Point: 132°C
DOT/IATA/IMDG: UN2923 - HC 8(6.1) - PG II
Risk Statements: R25,R34,R41,R43,R50
Safety Statements: S13,S22,S24/25,S26,S27,S36/37/39,S45,S61
Uses of o-Phthalaldehyde:
o-Phthalaldehyde can be widely used for precolumn derivatization of amino acids in HPLC separation or Capillary electrophoresis.
For flow cytometric measurements of protein thiol groups.
o-Phthalaldehyde can be used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups.
Precolumn derivatization reagent for primary amines and amino acids.
The fluorescent derivative can be detected by reverse-phase HPLC.
The reaction requires OPA, primary amine and a sulfhydryl.
In the presence of excess sulfhydryl, amines can be quantitated.
Disinfectant.
Reagent in fluorometric determination of primary amines and thiols.
o-Phthalaldehyde is used as a disinfectant and in the fluorometric determination of primary amines and thiols;Used to sterilize medical and dental equipment, as an enzyme inhibitor, indicator, chemical intermediate, diagnostic agent, tanning agent for leather, in water treatment, pulp and paper manufacturing, oil field water flooding, hair colorings, wood treatment, and antifouling paints
In winemaking
The Nitrogen by O-Phthaldialdehyde Assay (NOPA) is one of the methods used in winemaking to measure yeast assimilable nitrogen (or YAN) needed by wine yeast in order to successfully complete fermentation.
o-Phthalaldehyde is used in the following products: biocides (e.g. disinfectants, pest control products).
o-Phthalaldehyde is used in the following areas: health services.
Other release to the environment of o-Phthalaldehyde is likely to occur from: indoor use as processing aid and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).
Product Number: P0280
Purity / Analysis Method: >99.0%(GC)
Molecular Formula / Molecular Weight: C8H6O2 = 134.13
Physical State (20 deg.C): Solid
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Air Sensitive
CAS RN: 643-79-8
Reaxys Registry Number: 878317
PubChem Substance ID: 87574516
SDBS (AIST Spectral DB): 1434
Merck Index (14): 7368
MDL Number: MFCD00003335
Article No.: 05270
Grade: AR
CAS No.: 643-79-8
Molecular Formula: C8H6O2
Molecular Weight: 134.14
H.S. Code: 2912.2990
Shelf Life: 24 Months
Identifiers of o-Phthalaldehyde:
CAS Number: 643-79-8
ChEBI: CHEBI:70851 check
ChemSpider: 4642
ECHA InfoCard: 100.010.367
EC Number: 211-402-2
RTECS number: TH6950000
UNII: 4P8QP9768A
UN number 2923
CompTox Dashboard (EPA): DTXSID6032514
InChI: InChI=1S/C8H6O2/c9-5-7-3-1-2-4-8(7)6-10/h1-6H
SMILES: O=Cc1ccccc1C=O
Properties of o-Phthalaldehyde:
Formulation: 0.8 mg/mL o-phthalaldehyde (OPA) in proprietary buffer, pH 10
Form: Clear, colorless to slightly yellow liquid
Reactive toward: Primary amines (—NH2)
Detection: Fluorescence (excitation/emission = 340 nm/455 nm)
Application: Pre- or post-column derivatization for detection by HPLC
Melting Point: 56 °C
Boiling Point: 84 °C/0.8 mmHg
Solubility (soluble in): Methanol
Chemical formula: C8H6O2
Molar mass: 134.134 g·mol−1
Appearance: Yellow solid
Density: 1.19 g/mL
Melting point: 55.5 to 56 °C (131.9 to 132.8 °F; 328.6 to 329.1 K)
Boiling point: 266.1 °C (511.0 °F; 539.2 K)
Solubility in water: Low
o-Phthalaldehyde.
The α,α,α',α'-tetrabromo-o-xylene (344–370 g.) obtained as described above, part A, is placed in a 5-l. round-bottomed flask with 4 l. of 50% (by volume) ethanol and 275 g. of potassium oxalate.
The mixture is heated under reflux for 50 hours (a clear yellow solution is formed after 25–30 hours).
About 1750 ml. of the ethanol is then removed by distillation (which is stopped before the product begins to steam-distil), and 700 g. of disodium monohydrogen phosphate dodecahydrate (Na2HPO4 · 12H2O) is added to the aqueous residue.
The mixture is steam-distilled rapidly (Note 4), using an efficient condenser, until 10–12 l. of distillate is collected and the distillate no longer gives a black color test for o-phthalaldehyde3 when a portion is treated with concentrated ammonium hydroxide followed by glacial acetic acid.
The distillate is then saturated with sodium sulfate at room temperature and divided into portions of approximately 4 l.; each portion is extracted first with 200 ml. and then with six 100-ml. portions of ethyl acetate.
The combined ethyl acetate extracts are dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure.
The residue is crystallized from 90–100° ligroin, and a second crop is obtained by concentration of the mother liquor.
The total yield of o-phthalaldehyde, m.p. 55.5–56°, is 87–94 g. (74–80% based on the tetrabromide, or 59–64% based on o-xylene).
pH: 7
Melting Point: 54°C
Packaging: Glass Jar
Quantity: 5g
SMILES: O=CC1=CC=CC=C1C=O
Molecular Weight (g/mol): 134.13
ChEBI: CHEBI:70851
Physical Form: Solid
Molecular Weight: 134.13
XLogP3: 1.2
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 2
Exact Mass: 134.036779430
Monoisotopic Mass: 134.036779430
Topological Polar Surface Area: 34.1 Ų
Heavy Atom Count: 10
Formal Charge: 0
Complexity: 115
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Isomeric phthalaldehydes:
isophthalaldehyde (benzene-1,3-dicarbaldehyde)
terephthalaldehyde (benzene-1,4-dicarbaldehyde)
IUPAC name:
Phthalaldehyde
Preferred IUPAC name:
Benzene-1,2-dicarbaldehyde
Other name:
Benzene-1,2-dicarboxaldehyde
o-Phthalaldehyde
o-Phthalic dicarboxaldehyde
Phthaldialdehyde
Synonyms of Phthalaldehyde:
o-Phthalaldehyde
643-79-8
PHTHALALDEHYDE
o-Phthaldialdehyde
1,2-Benzenedicarboxaldehyde
Benzene-1,2-dicarboxaldehyde
Phthaldialdehyde
Phthalic aldehyde
Phthalic dialdehyde
Phthalyldicarboxaldehyde
ortho-Phthalaldehyde
Phthalic dicarboxaldehyde
o-Phthaldehyde
benzene-1,2-dicarbaldehyde
Phthalaldialdehyde
o-Phthalicdicarboxaldehyde
1,2-Diformylbenzene
2-PHTHALALDEHYDE
1,2-Phthalic dicarboxaldehyde
ortho Phthalaldehyde
o-Phthalic dicarboxaldehyde
OPA
1,2-BENZENEDICARBALDEHYDE
OPTA
NSC 13394
UNII-4P8QP9768A
CHEBI:70851
2-PHTHALDIALDEHYDE
MFCD00003335
4P8QP9768A
1,2-Benzenedicarboxaldehyde, homopolymer
NCGC00166206-01
DSSTox_CID_12514
DSSTox_RID_78962
DSSTox_GSID_32514
25750-62-3
Phtalaldehydes
Phtalaldehydes [French]
CAS-643-79-8
EINECS 211-402-2
BRN 0878317
phthalaldehyd
o-Phthalaldehyd
o-phthal aldehyde
orthophthalaldehyde
Phtharal (JAN)
Disopa (TN)
2-PHTHALDEHYDE
Phthaldialdehyde Reagent
o-Phthalaldehyde-[d6]
ORTHO-PHTHALADEHYDE
Epitope ID:176774
O-PHTHALIC DIALDEHYDE
2-Phthaldehyde, High purity
SCHEMBL33393
Benzene-1,2-dicarboxakdehyde
4-07-00-02138
1,2-Phthalic dicarboxyaldehyde
CHEMBL160145
Ortho-Phthalic Aldehyde (OPA)
BENZENE-1,2-DIALDEHYDE
DTXSID6032514
HSDB 8456
TIMTEC-BB SBB008450
BCP29465
NSC13394
STR01056
ZINC1729594
Tox21_112347
Tox21_300404
1,2-Benzenedialdehyde;Phthalaldehyde
BBL027435
NSC-13394
STK802214
AKOS000119186
Tox21_112347_1
AS03002
CS-W013385
LS11855
MCULE-5731001647
NCGC00166206-02
NCGC00166206-04
NCGC00254339-01
AC-10388
FLUORALDEHYDE(TM) O-PHTHALALDEHYDE
Phthaldialdehyde Reagent, Solution Complete
AM20050101
FT-0632732
P0280
Phthaldialdehyde Reagent, Solution Incomplete
43P798
D03470
P-6600
SR-01000944839
Q5933776
SR-01000944839-
Phthaldialdehyde, for fluorescence, >=99.0% (HPLC)
6-Oxomethylene-5-[(E)-hydroxymethylene]cyclohexa-1,3-diene
6-Oxomethylene-5-[(Z)-hydroxymethylene]cyclohexa-1,3-diene
Phthaldialdehyde, >=97% (HPLC), powder (may contain lumps)
Phthaldialdehyde, suitable for HPLC fluorimetric detection of amino acids, >=99% (HPLC), powder
MeSH of o-Phthalaldehyde:
Aldehyde, ortho-Phthalic
o Phthalaldehyde
o Phthaldialdehyd
o-Phthalaldehyde
o-Phthaldialdehyde
ortho Phthalaldehyde
ortho Phthalic Aldehyde
ortho-Phthalaldehyde
ortho-Phthalic Aldehyde
Orthophthaldialdehyde