Methylhydroquinone (HCID 7253)

Overview

Toluquinol is a member of the class of hydroquinones that is hydroquinone in which one of the benzene hydrogens has been replaced by a methyl group. It has a role as an angiogenesis inhibitor, an anti-inflammatory agent and a Penicillium metabolite.

Names & identifiers

Preferred name: Methylhydroquinone
IUPAC: 2-methylbenzene-1,4-diol
English name: 2-Methylhydroquinone
Molecular formula: C7H8O2
Molecular weight: 124.14

Names & synonyms

Methylhydroquinone95-71-62-Methylhydroquinone2-methylbenzene-1,4-diol2,5-DihydroxytolueneToluhydroquinonep-ToluhydroquinoneToluquinolp-Toluquinolp-ToluhydroquinolTolylhydroquinone2,5-Toluenediol

Show more names

THQ

2-Methyl-1,4-benzenediol1,4-Benzenediol, 2-methyl-1,4-Dihydroxy-2-methylbenzene2-Methyl-1,4-hydroquinoneDTXSID4020876332W51E0OCNSC-4962DTXCID00876

Database identifiers

CAS: 95-71-6
PubChem CID: 7253
DTXSID: DTXSID4020876
ChEMBL: CHEMBL450917
ChEBI: CHEBI:133842
UNII: 332W51E0OC
EC Number: 202-443-7
Nikkaji: J4.712K

Properties

Computed structural properties

XLogP: 1
Topological polar surface area: 40.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 9
Formal charge: 0
Complexity: 92.9

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Phenols

Vapor Pressure0.0028 [mmHg]

Physical Description · 2 items

Dry Powder

Off-white solid with a slight odor; [Eastman Chemical MSDS]

Physicochemical properties

Melting point: 128 · 128-130 °C(lit.)
Boiling point: 285 °C · 285°C
Density: 1.1006 · 1.1006 (rough estimate)
vapor pressure: 0.004 Pa · 0.004Pa at 25℃
refractive index: 1.4922 · 1.4922 (estimate)
Flash point: 172 °C · 172 °C
storage temp.: 30 °C · Store below +30°C.
solubility: 77 g/l · 77g/l
pka: 1 · pK1:10.03;pK2:11.62 (25°C)
form: Crystalline Powder
color: Grayish-white to light beige
Water Solubility: 77 g/L · 77 g/L (25 ºC)
BRN: 2041489 · 2041489
Stability: Stable. Combustible. Incompatible with oxidizing agents, strong bases.
InChI: 1S/C7H8O2/c1-5-4-6(8)2-3-7(5)9/h2-4,8-9H,1H3
InChIKey: CNHDIAIOKMXOLK-UHFFFAOYSA-N
SMILES: Cc1cc(O)ccc1O
LogP: 0.9 at · 0.9 at 27℃
CAS DataBase Reference: 95 · 95-71-6(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 332 W51E0OC · 332W51E0OC
NIST Chemistry Reference: 1 · 1,4-Benzenediol, 2-methyl-(95-71-6)
EPA Substance Registry System: 2 · 2-Methylhydroquinone (95-71-6)
UNSPSC Code: 12352104 · 12352104
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335-H312
Precautionary statements: 280 · P280-P304+P340-P405-P501a-P301+P312+P330-P305+P351+P338-P261
target organs: Respiratory system
Hazard Codes: Xi,Xn
Risk Statements: 36 · 36/37/38-22
Safety Statements: 26 · 26-36
RIDADR: 2811 · 2811
WGK Germany: 2 · 2
RTECS: 6700000 · MX6700000
Autoignition Temperature: 851 °F · 851 °F
TSCA: TSCA listed
HazardClass: 6.1 · 6.1(b)
PackingGroup: III
HS Code: 29072900 · 29072900
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1ASkin Sens. 1STOT SE 3
Toxicity: 50 orally · LD50 orally in Rabbit: 200 - 400 mg/kg
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.1% (5 of 467) of reports.

Danger

H302 (94%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 467 reports by companies from 28 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 1,4-Benzenediol, 2-methyl-

1,4-Benzenediol, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenediol, 2-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 05-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/27614

Methylhydroquinone: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin and eye irritant; Dust causes eye and respiratory tract irritation; Harmful by ingestion; [Eastman Chemical MSDS] See Hydroquinone.

Hazard Classes and CategoriesAcute Tox. 4 (94%)

Safety data

wgk: 2
tsca: TSCA listed
rtecs: MX6700000
ridadr: 2811
hs_code: 29072900
Toxicity: LD50 orally in Rabbit: 200 - 400 mg/kg
risk_code: 36/37/38-22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi,Xn
safety_code: 26-36
hazard_class: 6.1(b)
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: III
target organs: Respiratory system
Hazard statements: H302-H315-H319-H335-H312
REACH Registrations: Active
Hazard Classifications: Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1ASkin Sens. 1STOT SE 3
Autoignition Temperature: 851 °F
Precautionary statements: P280-P304+P340-P405-P501a-P301+P312+P330-P305+P351+P338-P261

Chemistry & industry

Uses & manufacturing

UsesUsed as an inhibitor; [Eastman Chemical MSDS]

U.S. Production2023: 22,046 lb

Industry UsesCorrosion inhibitor

General Manufacturing Information · 2 items

All Other Chemical Product and Preparation Manufacturing

1,4-Benzenediol, 2-methyl-: ACTIVE

Applications · 4 items

UsesAntioxidant, polymerization inhibitor.

UsesMethylhydroquinone is used as stabilizer and antioxidant in aerylic monomers to prevent polymerization.

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

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

Upstream & downstream products

Downstream products

2,5-Dimethoxybenzylamine 3-Methyl-4-nitrophenol Benzoic acid, 4-[4-[(1-oxo-2-propenyl)oxy]butoxy]-, 2-Methyl-1,4-phenylene ester 2,5-DIMETHOXY-4-METHYLBENZALDEHYDE 1,4-BENZENEDIETHANOL 3,4-Dimethoxytoluene 2,5-Di(Methoxy-d3)-4-Methylbenzaldehyde 1,4-BIS-[4-(6-ACRYLOYLOXYHEXYLOXY)BENZOYLOXY]-2-METHYLBENZENE 1,4-Bis-[4-(3-acryloyloxypropyloxy)benzoyloxy]-2-methylbenzene

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]

Additional notes

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