TOLUHYDROQUINONE

CAS Number: 95-71-6
Synonym(s): Methylhydroquinone
Linear Formula: CH3C6H3-1,4-(OH)2
Molecular Weight: 124.14

Toluhydroquinone is a versatile compound.
Toluhydroquinone finds many applications in the field of polymer science due to its good binding properties as well as its strength.

Toluhydroquinone is an off-white crystalline solid with a molecular weight of 124.137 g/mol.
Toluhydroquinone has a characteristic odor and its melting point is 262.4°F.

Toluhydroquinone is a reactive oxygen species (ROS) that can bind to DNA, forming covalent adducts.
Toluhydroquinone has been shown to have an optimum concentration of 10 μM, and the hydroxyl group on its phenolic ring enables it to form hydrogen bonding interactions with nucleic acids.
Toluhydroquinone has been shown to inhibit angiogenic process in vitro and in vivo, as well as inhibiting the growth of tumor cells by binding to DNA.
Toluhydroquinone also inhibits the transfer of methyl groups from methyl donors such as S-adenosylhomocysteine and methionine to acceptor molecules such as p-hydroxybenzoic acid.

Toluhydroquinone (Methylhydroquinone) Chemical which is a tan to white crystalline solid.
Toluhydroquinone is a highly active inhibitor in the free radical polymerization of vinyl monomers and unsaturated polyesters.

Toluhydroquinone undergoes chemical reactions similar to those of hydroquinone.
The presence of a methyl group in the ortho position in the toluhydroquinone molecule is the slight structural and behavioral difference between toluhydroquinone and hydroquinone.

Application Area of Toluhydroquinone:
Toluhydroquinone is used as a stabilizer for unsaturated polyesters and as an antioxidant for fatty esters, linseed oil, and other nonfood fats and oils
Toluhydroquinone is used as a stabilizer to inhibit peroxide formation in ethers, chlorinated hydrocarbons and ethyl cellulose
Toluhydroquinone is also used as an intermediate to manufacture other stabilizers, dyes, pharmaceuticals and plasticizers

Applications of Toluhydroquinone:
Toluhydroquinone has the following applications.

Toluhydroquinone is used as a general adhesive and binding agent in various preparations.
In the automotive industry, Toluhydroquinone is widely used for repair as well as maintenance and also caring for automobiles viz, auto shampoo, wax, polish, brake grease.

Binders are the main ingredient of any paint.
Binders are polymers that form a continuous film on a solid surface.
Binders ensure that the coating is evenly spread and well adsorbed on to the surface.

The binders also have the major role of holing the pigment molecules responsible for color evenly across the coating.
Toluhydroquinone is one of the most widely used a binder for paints.

The technology of thermal insulation of buildings is one of the many steps that men have taken for a sustainable future.
Thermal insulation of buildings reduces energy consumption and prevent heat loss or gain by buildings.
Toluhydroquinone is used for thermal insulation as well as soundproofing.

In the construction of buildings and ships, Toluhydroquinone is used for plumbing, electrical work, and also bricklaying.
Toluhydroquinone is also used to repair sporting boats.

Beilstein:
2041489

EC Number:
202-443-7

MDL number:
MFCD00002345

PubChem Substance ID:
24847123

NACRES:
NA.22

Toluhydroquinone is a reactive oxygen species (ROS) that can bind to DNA, forming covalent adducts.

KEYWORDS:
95-71-6, Methylhydroquinone, 2 5-Dihydroxytoluene, p-Toluhydroquinone, 1 4-Benzenediol 2-methyl-, Pyrolin, NSC 4962, UNII-332W51E0OC, MFCD00002345, NSC4962

Toluhydroquinone Definition:
Toluhydroquinone or Toluquinol belongs to a class of compounds called Hydroquinones with one of the benzene hydrogens replaced by a methyl group.

DESCRIPTION of Toluhydroquinone:
General description:
Toluhydroquinone is produced by the oxidation of o-cresol by the mutants G103S, G103S/A107G, and G103S/A107T.

Applications of Toluhydroquinone:
Toluhydroquinone can be used as a reactant to prepare:
-A semiflexible thermotropic polyester via polycondensation reaction with 4,4′-sebacoyldioxydibenzoyl chloride.
-A sesquiterpene (±)-helibisabonol A.
-poly{hexakis[(methyl)(4-hydroxyphenoxy)]cyclotriphosphazene} by reacting with hexachlorocyclotriphosphazene.
-6-Hydroxy-4,7-dimethyl-2H-1-benzopyran-2-one by treating with ethyl acetoacetate in the presence of H2SO4 as a catalyst.

Biochem/physiol Actions of Toluhydroquinone:
Toluhydroquinone (Toluquinol) inhibits the growth of endothelial and tumor cells in culture in the micromolar range and is a promising drug candidate in the treatment of cancer and other angiogenesis-related pathologies.

About Toluhydroquinone Helpful information:
Toluhydroquinone 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.
Toluhydroquinone is used by consumers, by professional workers (widespread uses), in formulation or re-packing and at industrial sites.

Consumer Uses of Toluhydroquinone:
Toluhydroquinone is used in the following products: coating products.
Other release to the environment of Toluhydroquinone is likely to occur from: indoor use and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives).

Article service life of Toluhydroquinone:
ECHA has no public registered data on the routes by which Toluhydroquinone is most likely to be released to the environment.
ECHA has no public registered data indicating whether or into which articles Toluhydroquinone might have been processed.

Widespread uses by professional workers of Toluhydroquinone:
Toluhydroquinone is used in the following products: coating products, fillers, putties, plasters, modelling clay and polymers.
Toluhydroquinone is used in the following areas: building & construction work.
Toluhydroquinone is used for the manufacture of: plastic products.
Other release to the environment of Toluhydroquinone 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) and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives).

Formulation or re-packing of Toluhydroquinone:
Toluhydroquinone is used in the following products: polymers, coating products, fillers, putties, plasters, modelling clay, adhesives and sealants and laboratory chemicals.
Release to the environment of Toluhydroquinone can occur from industrial use: formulation of mixtures and formulation in materials.

Uses at industrial sites of Toluhydroquinone:
Toluhydroquinone is used in the following products: coating products, laboratory chemicals, polymers, fillers, putties, plasters, modelling clay and adhesives and sealants.
Toluhydroquinone is used for the manufacture of: chemicals and plastic products.
Release to the environment of Toluhydroquinone can occur from industrial use: as processing aid, as processing aid, in the production of articles, as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites and for thermoplastic manufacture.

Manufacture of Toluhydroquinone:
ECHA has no public registered data on the routes by which Toluhydroquinone is most likely to be released to the environment.

Product Information of Toluhydroquinone:
CAS number: 95-71-6
EC number: 202-443-7
Hill Formula: C₇H₈O₂
Chemical formula: 2-(CH₃)C₆H₃-1,4-(OH)₂
Molar Mass: 124.14 g/mol
HS Code: 2907 29 00

What is Toluhydroquinone and where is it found?
Toluhydroquinone is used as a stabilizer in acrylics and as an antioxidant for fatty esters, linseed oil and other inedible fats and oils.
Further research may identify additional product or industrial usages of this chemical.

What else is Toluhydroquinone called?
Toluhydroquinone can be identified by different names, including:
2,5-Dihydroxytoluene 2,5-toluenediol, 2-methyl-1,4-benzenediol 2-Toluhydroquinone Methyl-p-hydroquinone, P-toluquinol, Toluhydroquinone

Description of Toluhydroquinone:
Catalogue Number: 820801
Synonyms: 2,5-Dihydroxytoluene, Toluhydroquinone
Description: 2-Toluhydroquinone

Physicochemical Information of Toluhydroquinone:
Flash point: 172 °C
Ignition temperature: 468 °C
Melting Point: 128 - 130 °C
Solubility: 77 g/l

Specifications of Toluhydroquinone:
Assay (HPLC, area%): ≥ 97.0 % (a/a)
Melting range (lower value): ≥ 125 °C
Melting range (upper value): ≤ 128 °C
Identity (IR): passes test

Purity: >98.0%(T)

Product Description of Toluhydroquinone:
Catalogue Number: M312535
Chemical Name: Toluhydroquinone

Synonyms:
2,5-Dihydroxytoluene; 2,5-Toluenediol; 2-Methyl-1,4-benzenediol; 2-Methyl-1,4-dihydroxybenzene; 2-Methyl-1,4-hydroquinone; 2-Methyl-p-hydroquinone; 2-Toluhydroquinone; 4-Hydroxy-2-methylphenol; M-HQ; Methyl 1,4-dihydroxybenzene; Methyl-p-hydroquinone; Toluhydroquinone; NSC 4962; THQ; Toluhydroquinone; Tolylhydroquinone; m-Methyl-hydroquinone; o-Toluhydroquinone; p-Toluhydroquinol; p-Toluhydroquinone; p-Toluquinol; 1,4-Dihydroxy-2-methylbenzene

CAS Number: 95-71-6
Molecular Formula: C7H8O2
Molecular Weight: 124.14

Category of Toluhydroquinone:
Standards; Pharmaceutical/API Drug Impurities/Metabolites;

Applications of Toluhydroquinone:
Toluhydroquinone is a marine fungus metabolite, showing activity as an angiosupressor that interferes with the Akt pathway.
Allows for screening of novel inhibitors of angiogenesis.

Synonyms:
2,5-Dihydroxytoluene
p-Toluhydroquinone

2-Toluhydroquinone Chemical Properties,Uses,Production:

Chemical Properties of Toluhydroquinone:
white solid

Uses of Toluhydroquinone:
Antioxidant, polymerization inhibitor.

Uses of Toluhydroquinone:
Toluhydroquinone is used as stabilizer and antioxidant in aerylic monomers to prevent polymerization.

Uses of Toluhydroquinone:
Toluhydroquinone is a marine fungus metabolite, showing activity as an angiosupressor that interferes with the Akt pathway.
Allows for screening of novel inhibitors of angiogenesis.

Definition of Toluhydroquinone:
ChEBI: A member of the class of hydroquinones that is hydroquinone in which one of the benzene hydrogens has been replaced by a methyl group.

General Description of Toluhydroquinone:
Toluhydroquinone is produced by the oxidation of o-cresol by the mutants G103S, G103S/A107G, and G103S/A107T.

Purification Methods of Toluhydroquinone:
Crystallise the quinone from EtOH.

Toluhydroquinone Properties:
Melting point: 128-130 °C(lit.)
Boiling point: 285°C
Density: 1.1006 (rough estimate)
refractive index: 1.4922 (estimate)
Flash point: 172 °C
storage temp.: Store below +30°C.
solubility: 77g/l
form: Crystalline Powder
pka: pK1:10.03;pK2:11.62 (25°C)
color: Grayish-white to light beige
Water Solubility: 77 g/L (25 ºC)
BRN: 2041489
Stability: Stable. Combustible. Incompatible with oxidizing agents, strong bases.
InChIKey: CNHDIAIOKMXOLK-UHFFFAOYSA-N
CAS DataBase Reference: 95-71-6(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: 332W51E0OC
NIST Chemistry Reference: 1,4-Benzenediol, 2-methyl-(95-71-6)
EPA Substance Registry System: 2-Toluhydroquinone (95-71-6)

PROPERTIES of Toluhydroquinone:
Quality Level:
100

assay:
99%

form:
solid

autoignition temp.:
851 °F

mp:
128-130 °C (lit.)

SMILES string:
Cc1cc(O)ccc1O

InChI:
1S/C7H8O2/c1-5-4-6(8)2-3-7(5)9/h2-4,8-9H,1H3

InChI key:
CNHDIAIOKMXOLK-UHFFFAOYSA-N

Product Number: M0342
Purity / Analysis Method: >98.0%(T)
Molecular Formula / Molecular Weight: C7H8O2 = 124.14
Physical State (20 deg.C). Solid
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Light Sensitive,Air Sensitive
CAS RN: 95-71-6
Reaxys Registry Number: 2041489
PubChem Substance ID: 87572412
SDBS (AIST Spectral DB): 3439
MDL Number: MFCD00002345

Toluhydroquinone (MeHQ) or methyl ether derivative thereof is prepared by contacting paramethoxyphenol or para-dimethoxybenzene with an acid catalyst, preferably a solid acid catalyst, at a temperature ranging from 100° to 300° C.

Property Name: Property Value
Molecular Weight: 124.14
XLogP3: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 124.052429494
Monoisotopic Mass: 124.052429494
Topological Polar Surface Area: 40.5 Å²
Heavy Atom Count: 9
Formal Charge: 0
Complexity: 92.9
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

CAS:
95-71-6

Molecular Formula:
C7H8O2

Molecular Weight (g/mol):
124.14

MDL Number:
MFCD00002345

InChI Key:
CNHDIAIOKMXOLK-UHFFFAOYSA-N

Synonym:
Toluhydroquinone, 2-Toluhydroquinone, 2,5-dihydroxytoluene, p-toluhydroquinone, toluhydroquinone, toluquinol, p-toluquinol, tolylhydroquinone, p-toluhydroquinol, 2,5-toluenediol

PubChem CID:
7253

IUPAC Name:
2-methylbenzene-1,4-diol

SMILES:
CC1=CC(O)=CC=C1O

Toluhydroquinone
2-Toluhydroquinone
95-71-6
2-methylbenzene-1,4-diol
2,5-Dihydroxytoluene
Toluhydroquinone
p-Toluhydroquinone
Toluquinol
p-Toluquinol
Tolylhydroquinone
p-Toluhydroquinol
2,5-Toluenediol
Methyl-p-hydroquinone
1,4-Benzenediol, 2-methyl-
1,4-Dihydroxy-2-methylbenzene
2-Methyl-1,4-benzenediol
METHYL HYDROQUINONE
Hydroquinone, methyl-
Hydroquinone, tolyl-
Pyrolin
2-Methyl-1,4-hydroquinone
NSC 4962
UNII-332W51E0OC
MFCD00002345
NSC4962
332W51E0OC
EINECS 202-443-7
BRN 2041489
2-Methyl-benzene-1,4-diol
methylhydroquinon
3-methyl-1,4-dihydroxybenzene
AI3-14932
2-methylhydroquinol
methyl-p-hydroquinol
monoToluhydroquinone
2-methyl hydroquinone
2-Methyl-hydroquinone
monomethyl hydroquinone
2-Methyl-p-hydroquinone
DSSTox_CID_876
Toluhydroquinone, 99%
3-methyl-4-hydroxyphenol
4-hydroxy-2-methylphenol
EC 202-443-7
2-Methylbenzene-1,4-diole
DSSTox_RID_75840
Toluhydroquinone, >=99%
WLN: L6V DVJ X1
DSSTox_GSID_20876
SCHEMBL36349
2,5-Dihydroxytoluene polymer
2,5-DHTOP
4-06-00-05866 (Beilstein Handbook Reference)
2-methyl-1,4-dihydroxybenzene
CHEMBL450917
WLN: L6V DVJ XR X1
3-metyl-1,4-dihydroxy benzene
DTXSID4020876
2-methyl-1,4-dihydroxy benzene
CHEBI:133842
BDBM176768
ZINC388086
NSC-4962
Tox21_200506
AKOS015856210
AC-4660
CS-W013533
MCULE-7035325950
CAS-95-71-6
NCGC00248664-01
NCGC00258060-01
AS-15442
CAS# 95-71-6
P353
FT-0613052
M0342
Toluhydroquinone, purum, >=98.0% (HPLC)
E83005
US9688816, 8
Q1925586
W-109360
F0001-2277
N-a-Fmoc-N-?-allyloxycarbonyl-L-2,3-diaminopropionicacid
7DV
2-Methyl-p-hydroquinone
1,4-Benzenediol, 2-methyl- [ACD/Index Name]
202-443-7 [EINECS]
2041489 [Beilstein]
2-Methyl-1,4-benzenediol [ACD/IUPAC Name]
2-Méthyl-1,4-benzènediol [French] [ACD/IUPAC Name]
2-Methyl-1,4-benzoldiol [German] [ACD/IUPAC Name]
2-Methylbenzene-1,4-diol [ACD/IUPAC Name]
2-Toluhydroquinone [ACD/IUPAC Name]
95-71-6 [RN]
Toluhydroquinone
MFCD00002345 [MDL number]
MX6700000
QR DQ B1 [WLN]
"1,4-BENZENEDIOL, 2-METHYL-"
"1,4-BENZENEDIOL, 2-METHYL-"|"2-METHYLBENZENE-1,4-DIOL"
"2-METHYLBENZENE-1,4-DIOL"
p-toluquinol
1-(3,4-Dihydroxyphenyl)-2-propanone
1,4-Dihydroxy-2-methylbenzene
135648-79-2 [RN]
140627-29-8 [RN]
2,4-DCT
2,5-DHTOP
2,5-Dihydroxytoluene
2,5-Dihydroxytoluene, Toluhydroquinone
2,5-Toluenediol
202-443-7MFCD00002345
202-445-8 [EINECS]
29763-99-3 [RN]
2-METHYLHYDROQUI
2-Toluhydroquinone;2,5-Dihydroxytoluene
4-05-00-00815 [Beilstein]
4-06-00-05866 (Beilstein Handbook Reference) [Beilstein]
437-50-3 [RN]
65916-21-4 [RN]
78446-96-5 [RN]
7DV
95-73-8 [RN]
96937-50-7 [RN]
EINECS 202-443-7
Gentisin
Hydroquinone, methyl-
Toluhydroquinone, ???
Toluhydroquinone|2,5-Dihydroxytoluene
Methyl-p-hydroquinone
PHENOXY, 4-HYDROXY-2-METHYL-
S1
THQ (VAN)
WLN: L6V DVJ X1
WLN: L6V DVJ XR X1

Regulatory process names:
2-Toluhydroquinone
2-Toluhydroquinone

CAS names:
1,4-Benzenediol, 2-methyl-

IUPAC names:
2-METHYL HYDROQUINONE
2-Methyl-1,4-benzenediol
2-methylbenzene-1,4-diol
2-Toluhydroquinone
2-Toluhydroquinone
Toluhydroquinone
Toluhydroquinone

Other identifiers:
135648-79-2
140627-29-8
29763-99-3
65916-21-4
78446-96-5
95-71-6
96937-50-7