1-Methylimidazole or N-methylimidazole is an aromatic heterocyclic organic compound with the formula CH3C3H3N2.
1-Methylimidazole is a colourless liquid that is used as a specialty solvent, a base, and as a precursor to some ionic liquids.
1-Methylimidazole is a fundamental nitrogen heterocycle and as such mimics for various nucleoside bases as well as histidine and histamine.
CAS Number: 616-47-7
EC Number: 210-484-7
Molecular Formula: C₄H₆N₂
Molecular Weight: 82.1
1-Methylimidazole is a colorless to yellow liquid, with an amine-like odor.
1-Methylimidazole is miscible with water.
1-Methylimidazole is a versatile intermediate with a variety of applications.
1-Methylimidazole is a versatile intermediate used as a building block for active ingredients as well as in epoxy curing.
1-Methylimidazole, also known as N-Methylimidazole, is used as a specialty solvent, a base, and as a precursor to some ionic liquids.
Basicity of 1-Methylimidazole:
With the N-methyl group, this particular derivative of imidazole cannot tautomerize.
1-Methylimidazole is slightly more basic than imidazole, as indicated by the pKa's of the conjugate acids of 7.0 and 7.4.
Methylation also provides a significantly lower melting point, which makes 1-methylimidazole a useful solvent.
Applications of 1-Methylimidazole:
1-Methylimidazole may be used as a starting material to synthesize: 1-(2-hydroxypropyl)-3-methylimidazolium salts used as ionic liquids1,3-dimethylimidazoyl-2-ylidene borane, a stable and easy to handle N-heterocyclic carbene boraneIt can act both as a catalyst and a solvent in the synthesis of aldononitrile acetates from aldoses.
General description of 1-Methylimidazole:
1-Methylimidazole is an N-donor ligand generally used in the preparation of coordinate complexes.
Synonyms:
n-Methyl Imidazole
Chemical Name:
1-methyl-1H-imidazole
Appearance of 1-Methylimidazole:
Colourless to yellowish liquid
Applications of 1-Methylimidazole:
Intermediate used in the production of:
Pharmaceuticals
Pesticides
Ion exchange resins
Photographic chemicals
Dye
Used as a catalyst for:
Hardeners for epoxy resins
Catalyst for polyurethanes
Synthesis of 1-Methylimidazole:
1-Methylimidazole is prepared mainly by two routes industrially.
The main one is acid-catalysed methylation of imidazole by methanol.
The second method involves the Radziszewski reaction from glyoxal, formaldehyde, and a mixture of ammonia and methylamine.
(CHO)2 + CH2O + CH3NH2 + NH3 → H2C2N(NCH3)CH + 3 H2O
1-Methylimidazole can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation.
Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation.
H2C2N(NH)CH + CH3I → [H2C2(NH)(NCH3)CH]I
[H2C2(NH)(NCH3)CH]I + NaOH → H2C2N(NCH3)CH + H2O + NaI
Applications of 1-Methylimidazole:
In the research laboratory, 1-methylimidazole and related derivatives have been used as mimic aspects of diverse imidazole-based biomolecules.
1-Methylimidazole is also the precursor for the synthesis of the methylimidazole monomer of pyrrole-imidazole polyamides.
These polymers can selectively bind specific sequences of double-stranded DNA by intercalating in a sequence dependent manner.
Ionic liquid precursor of 1-Methylimidazole:
1-Methylimidazole alkylates to form dialkyl imidazolium salts.
1-methylimidazole is used as a means to remove acid during their industrial-scale production of diethoxyphenylphosphine.
In this biphasic acid scavenging using ionic liquids (BASIL) process, 1-methylimidazole reacts with HCl to produce 1-methylimidazolium hydrochloride, which spontaneously separates as a separate liquid phase under the reaction conditions.
2 MeC3N2H3 + C6H5PCl2 + 2 C2H5OH → 2 [MeC3N2H4]Cl + C6H5P(OC2H5)2
Donor properties of 1-Methylimidazole:
1-methylimidazole (NMIz) as a ligand forms octahedral ions M(NMIz)62+with M = Fe, Co, Ni, and a square-planar ion Cu(NMIz)42+.
1-methylimidazole forms adducts with Lewis acids such as molybdenum perfluorobutyrate and [Rh(CO)2Cl]2.
The donor properties of 1-methylimidazole have been analyzed by the ECW model yielding EB= 1.16 and CB= 4.92.
Synonym(s): N-Methylimidazole
Empirical Formula (Hill Notation): C4H6N2
CAS Number: 616-47-7
Molecular Weight: 82.10
Beilstein: 105197
EC Number: 210-484-7
MDL number: MFCD00005292
PubChem Substance ID: 24896975
1-Methylimidazole is a metabolite of 1-methyl-2-thioimidazole (methimazole) which inhibits bone resorption.
The invention discloses a 1-methylimidazole preparation method.
The method allows 1-methylimidazole to be directly synthesized by adopting a fixed bed continuous flow reaction apparatus and treating ammonium metatungstate exchanged hydrotalcite as a catalyst, imidazole as a raw material and methanol as a methylation reagent, so the method has the advantages of low raw material cost, simple operation, less pollution, high yield and the like, and can easily realize the industrial production.
The dynamics of imidazole (IM) and 1-methylimidazole (1-MeIM) in the liquid phase at 95 °C were studied by IR polarization selective pump–probe and two-dimensional IR (2D IR) spectroscopies.
The two molecules are very similar structurally except that IM can be simultaneously a hydrogen bond donor and acceptor and therefore forms extended hydrogen-bonded networks.
The broader IR absorption spectrum and a shorter vibrational lifetime of the vibrational probe, selenocyanate anion (SeCN–), in IM vs 1-MeIM indicate that stronger hydrogen bonding exists between SeCN– and IM.
Molecular dynamics (MD) simulations support the strong hydrogen bond formation between SeCN– and IM via the HN moiety.
SeCN– makes two H-bonds with IM; it is inserted in the IM H-bonded chains rather than being a chain terminator.
The strong hydrogen bonding influenced the reorientation dynamics of SeCN– in IM, leading to a more restricted short time angular sampling (wobbling-in-a-cone).
The complete orientational diffusion time in IM is 1.7 times slower than in 1-MeIM, but the slow down is less than expected, considering the 3-fold larger viscosity of IM.
The jump reorientation mechanism accounts for the anomalously fast orientational relaxation in IM, and the MD simulations determined the average jump angle of the probe between hydrogen bonding sites.
Spectral diffusion time constants obtained from the 2D IR experiments are only modestly slower in IM than in 1-MeIM in spite of the significant increase in viscosity.
The results indicate that the spectral diffusion sensed by the SeCN– has IM hydrogen bond dynamics contributions not present in 1-MeIM.
About 1-Methylimidazole:
1-Methylimidazole is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
1-Methylimidazole is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses of 1-Methylimidazole:
ECHA has no public registered data indicating whether or in which chemical products 1-Methylimidazole might be used.
ECHA has no public registered data on the routes by which 1-Methylimidazole is most likely to be released to the environment.
Article service life of 1-Methylimidazole:
ECHA has no public registered data on the routes by which 1-Methylimidazole is most likely to be released to the environment.
ECHA has no public registered data indicating whether or into which articles 1-Methylimidazole might have been processed.
Widespread uses by professional workers of 1-Methylimidazole:
ECHA has no public registered data indicating whether or in which chemical products 1-Methylimidazole might be used.
ECHA has no public registered data on the types of manufacture using 1-Methylimidazole.
Other release to the environment of 1-Methylimidazole is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).
Formulation or re-packing of 1-Methylimidazole:
ECHA has no public registered data indicating whether or in which chemical products 1-Methylimidazole might be used.
Release to the environment of 1-Methylimidazole can occur from industrial use: formulation of mixtures.
Uses at industrial sites of 1-Methylimidazole:
1-Methylimidazole is used in the following products: coating products, pharmaceuticals, polymers and oil and gas exploration or production products.
1-Methylimidazole is used for the manufacture of: chemicals and plastic products.
Release to the environment of 1-Methylimidazole can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid, as processing aid and for thermoplastic manufacture.
Manufacture of 1-Methylimidazole:
Release to the environment of 1-Methylimidazole can occur from industrial use: manufacturing of the substance.
General description of 1-Methylimidazole:
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry.
1-Methylimidazole has been enhanced for catalysis.
Preferred IUPAC name:
1-Methyl-1H-imidazole
Other names:
1-Methylimidazole
N-Methylimidazole
NMI
Product Number: M3214
Purity / Analysis Method: >98.0%(T)(HPLC)
Molecular Formula / Molecular Weight: C5H7F3N2O3S = 232.18
Physical State (20 deg.C): Solid
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Hygroscopic
CAS RN: 99257-94-0
Reaxys Registry Number: 4614530
PubChem Substance ID: 468592341
MDL Number: MFCD18251289
1-Methylimidazole is a versatile intermediate used as a building block for active ingredients as well as in epoxy curing.
KEYWORDS:
616-47-7, 210-484-7, 3-methylimidazole, N-methyl-imidazol, 1-N-methylImidazole, Lopac-M-8878, 1-methyl-(1H)-imidazole, CHEMBL543, WLN: T5N CNJ A1, Lopac0_000831
Chemical Properties of 1-Methylimidazole:
1-Methylimidazole or N-methylimidazole is an aromatic heterocyclic organic compound with the formula CH3C3H3N2.
1-Methylimidazole is a colorless to yellow liquid, with an amine-like odor.
1-Methylimidazole is miscible with water.
1-Methylimidazole is an important raw material for the synthesis of pharmaceutical intermediates, used in the preparation of losartan, nizofenone, 1-Methyl-1H-imidazole-5-carbonyl chloride hydrochloride and naphazoline hydrochloride, etc.
1-Methylimidazole is also used as a specialty solvent, a base, and as a precursor to some ionic liquids.
Uses of 1-Methylimidazole:
1-Methylimidazole is used as a precursor for the synthesis of pyrrole-imidazole polyamides, ionic liquids such as 1-butyl-3-methylimidazolium hexafluorophosphate.
1-Methylimidazole is actively involved in removing acid during the production of diethoxyphenylphosphine.
1-Methylimidazole is used as an intermediate in organic synthesis.
Definition of 1-Methylimidazole:
ChEBI: 1-methyl-1H-imidazole is a 1H-imidazole having a methyl substituent at the N-1 position.
1-Methylimidazole is a metabolite of 1-methyl-2-thioimidazole (methimazole).
1-Methylimidazole inhibits bone resorption.
Preparation of 1-Methylimidazole:
1-Methylimidazole is prepared mainly by two routes industrially.
The main one is acid-catalysed methylation of imidazole by methanol.
The second method involves the Radziszewski reaction from glyoxal, formaldehyde, and a mixture of ammonia and methylamine.
(CHO)2 + CH2O + CH3NH2 + NH3 → H2C2N(NCH3)CH + 3 H2O
The compound can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation.
Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation.
H2C2N(NH)CH + CH3I → [H2C2(NH)(NCH3)CH]I
[H2C2(NH)(NCH3)CH]I + NaOH → H2C2N(NCH3)CH + H2O + NaI
General Description of 1-Methylimidazole:
1-Methylimidazole has been enhanced for catalysis.
1-Methylimidazole is a derivative of imidazole that is utilized in the manufacture of such classes of items as pharmaceuticals, pesticides, ion-exchange resins, dye intermediates, textile auxiliaries, photographic chemicals, and corrosion inhibitors.
1-Methylimidazole is also used as a catalyst for manufacturing polyurethanes and a curing agent for epoxy resins.
Flammability and Explosibility:
Notclassified
Purification Methods of 1-Methylimidazole:
Dry 1-Methylimidazole with sodium metal and then distil it.
Store 1-Methylimidazole at 0o under dry argon.
The picrate has m 159.5-160.5o (from H2O).
Catalogue Number: M312980
Chemical Name: 1-Methylimidazole
Synonyms: 1-Methyl-1H-imidazole; Araldite DY 070; DY 070; N-Methylimidazole; N1-Methylimidazole; NSC 88064
CAS Number: 616-47-7
Molecular Formula: C₄H₆N₂
Appearance: Colourless to Light Yellow Oil
Molecular Weight: 82.1
Storage: 4°C, Hygroscopic
Solubility: Chloroform (Slightly), Methanol (Slightly)
Stability: Hygroscopic
Category: Building Blocks; Miscellaneous;
Applications of 1-Methylimidazole:
A metabolite of 1-methyl-2-thioimidazole (methimazole).
1-Methylimidazole inhibits bone resorption.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
Identifiers of 1-Methylimidazole:
CAS Number: 616-47-7
Beilstein Reference: 105197
CHEBI: 113454 check
ChEMBL: ChEMBL543
ChemSpider: 1348
DrugBank: DB02671
ECHA InfoCard: 100.009.532
EC Number: 210-484-7
Gmelin Reference: 2403
PubChem CID: 1390
UNII : P4617QS63Y
CompTox Dashboard (EPA): DTXSID6052291
Properties of 1-Methylimidazole:
Melting point : −60 °C(lit.)
Boiling point: 198 °C(lit.)
Density: 1.03 g/mL at 25 °C(lit.)
vapor pressure: 0.4 mm Hg ( 20 °C)
refractive index: n20/D 1.495(lit.)
Flash point: 198 °F
storage temp.: Store below +30°C.
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Liquid
pka: 6.95(at 25℃)
Specific Gravity: 1.031
color: Clear colorless to yellow
PH: 9.5-10.5 (50g/l, H2O, 20℃)
PH Range: 9.5 - 11.5 at 100 g/l at 20 °C
explosive limit: 2.7-15.7%(V)
Water Solubility: Miscible with water.
Sensitive: Hygroscopic
BRN: 105197
Stability: Stable, but moisture sensitive. Incompatible with acids, acid anhydrides, strong oxidizing agents, moisture, carbon dioxide, acid chlorides.
InChIKey: MCTWTZJPVLRJOU-UHFFFAOYSA-N
LogP: -0.19 at 25℃
Properties of 1-Methylimidazole:
Chemical formula: C4H6N2
Molar mass: 82.10 g/mol
Density: 1.03 g/cm3
Melting point: −6 °C (21 °F; 267 K)
Boiling point: 198 °C (388 °F; 471 K)
Product Information of 1-Methylimidazole:
CAS number: 616-47-7
EC index number: 613-035-00-7
EC number: 210-484-7
Hill Formula: C₄H₆N₂
Molar Mass: 82.11 g/mol
HS Code: 2933 29 90
Physicochemical Information of 1-Methylimidazole:
Boiling point: 197 - 199 °C
Density: 1.035 g/cm3
Explosion limit: 2.7 - 15.7 %(V)
Flash point: 92 °C
Ignition temperature: 525 °C
Melting Point: -2 °C
pH value: 9.5 - 11.5 (100 g/l, H₂O, 20 °C)
Vapor pressure: 0.5 hPa (20 °C)
Synonyms:
1-methylimidazole
1-Methyl-1H-imidazole
1-Methylimidazole
105197 [Beilstein]
1H-Imidazole, 1-methyl- [ACD/Index Name]
1-Methyl-1H-imidazol [German] [ACD/IUPAC Name]
1-Methyl-1H-imidazole [ACD/IUPAC Name]
1-Méthyl-1H-imidazole [French] [ACD/IUPAC Name]
210-484-7 [EINECS]
616-47-7 [RN]
methylimidazole
MFCD00005292 [MDL number]
N-methylimidazole
110069-11-9 secondary RN [RN]
1123837-84-2 [RN]
1167574-49-3 secondary RN [RN]
1174917-56-6 secondary RN [RN]
1179540-68-1 secondary RN [RN]
120418-32-8 secondary RN [RN]
1235442-19-9 secondary RN [RN]
1246941-20-7 secondary RN [RN]
1259523-87-9 secondary RN [RN]
1357171-90-4 secondary RN [RN]
1359978-71-4 secondary RN [RN]
142504-34-5 secondary RN [RN]
1532594-45-8 secondary RN [RN]
16650-76-3 [RN]
1-methyl imidazole
1-methyl-imidazole
1-methylimidazole-d3
1-METHYLIMIDAZOLE-D3 (RING-D3)
1-Methylimidazole-d6
1MZ
210-484-7MFCD00005292
285978-27-0 [RN]
4166-68-1 [RN]
69723-05-3 secondary RN [RN]
DNA
imidazole, 1-methyl-
imidazole, methyl-
methyl-imidazole
missing
n-methyl imidazole
PS-9372
T5N CNJ A1 [WLN]
616-47-7
N-Methylimidazole
1H-Imidazole, 1-methyl-
IMIDAZOLE, 1-METHYL-
N-methylimidazol
1-methylimidazol
n-methyl imidazole
1-methyl-imidazole
1-methylimdazole
EINECS 210-484-7
UNII-P4617QS63Y
1-methyl-1h-imidazol
DTXSID6052291
CHEBI:113454
P4617QS63Y
NSC-88064
N1-Methylimidazole
Araldite DY 070
MFCD00005292
NSC 88064
cap b
lupragen(r) nmi
3-methylimidazole
N-methyl-imidazol
N-methyl-imidazole
1-methyl imidazole
1-N-methylImidazole
Lopac-M-8878
1-methyl-(1H)-imidazole
CHEMBL543
1-Methyl-1H-imidazole #
EC 210-484-7
WLN: T5N CNJ A1
Lopac0_000831
1-methyl-1H-imidazol-3-ium
3-methyl-1H-imidazol-3-ium
BDBM7884
DTXCID6030863
HMS3262H03
BCP29437
NSC88064
STR00990
Tox21_304006
Tox21_500831
BBL011447
STL146559
AKOS000119840
CCG-204915
CS-W008580
LP00831
PS-9372
SDCCGSBI-0050808.P002
NCGC00015702-01
NCGC00015702-02
NCGC00015702-03
NCGC00015702-04
NCGC00094162-01
NCGC00094162-02
NCGC00261516-01
NCGC00357222-01
1-Methylimidazole, ReagentPlus(R), 99%
CAS-616-47-7
DB-002020
THIAMAZOLE IMPURITY B [EP IMPURITY]
EU-0100831
FT-0632577
FT-0671848
M0508
EN300-21628
1-Methylimidazole, puriss., >=99.0% (GC)
D70869
M 8878
1-Methylimidazole, Vetec(TM) reagent grade, 98%
SR-01000076013
Q-200126
Q4545792
SR-01000076013-1
1-Methylimidazole, >=99%, purified by redistillation
F0001-1635
Z104506032
1-Methyl-1H-imidazole;N-Methylimidazole;1H-Imidazole, 1-methyl-
120418-32-8
Cap B (1-methylimidazole 16% in THF), for oligonucleotide synthesis, filtered through a 1mum filter
Regulatory process names:
1-methylimidazole
1H-Imidazole, 1-methyl-
Imidazole, 1-methyl-
N-Methylimidazole
Translated names:
1-methylimidazol (cs)
1-methylimidazol (da)
1-Methylimidazol (de)
1-methylimidazool (nl)
1-metilimidazol (es)
1-metilimidazol (hr)
1-metilimidazol (hu)
1-metilimidazol (ro)
1-metilimidazol (sl)
1-metilimidazolas (lt)
1-metilimidazole (pt)
1-metilimidazolo (it)
1-metilimidazols (lv)
1-metylimidazol (no)
1-metylimidazol (sk)
1-metylimidazol (sv)
1-metyloimidazol (pl)
1-Metyyli-imidatsoli (fi)
1-metüülimidasool (et)
1-méthylimidazole (fr)
1-μεθυλιμιδαζόλιο (el)
1-мeтилимидазол (bg)
IUPAC names:
1-Methyl-1H-imidazole
1-methyl-1H-imidazole
1-Methylimidazol
1-METHYLIMIDAZOLE
1-Methylimidazole
1-methylimidazole
1-Methylimidazole
1-methylimidazole
1H-Imidazole, 1-methyl-
METHYL-1 IMIDAZOLE
n-Methylinidazole
Trade names:
1-Methyl-1H-imidazole
1-Methylimidazole
Imidazole, 1-methyl- (6CI, 7CI, 8CI)
N-Methylimidazole
N-methylimidazole
N1-Methylimidazole
Other identifiers:
110069-11-9
1167574-49-3
1174917-56-6
1179540-68-1
120418-32-8
1235442-19-9
1246941-20-7
1259523-87-9
1357171-90-4
1359978-71-4
142504-34-5
1532594-45-8
1626357-11-6
1799662-03-5
1848219-06-6
613-035-00-7
616-47-7