Methylhydroquinone

Base Information

• Chemical Name: Methylhydroquinone
• CAS No.: 95-71-6
• Deprecated CAS: 135648-79-2,140627-29-8,29763-99-3,65916-21-4,78446-96-5,96937-50-7,140627-29-8,29763-99-3,65916-21-4,78446-96-5,96937-50-7
• Molecular Formula: C7H8O2
• Molecular Weight: 124.139
• Hs Code.: 29072900
• European Community (EC) Number: 202-443-7
• NSC Number: 4962
• UNII: 332W51E0OC
• DSSTox Substance ID: DTXSID4020876
• Nikkaji Number: J4.712K
• Wikidata: Q1925586
• Metabolomics Workbench ID: 134907
• ChEMBL ID: CHEMBL450917
• Mol file: 95-71-6.mol

Synonyms:2,5-dihydroxytoluene;2-methyl-1,4-hydroquinone;2-methylhydroquinone;toluquinol

Chemical Property of Methylhydroquinone

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0.00262mmHg at 25°C
• Melting Point: 128-130 °C(lit.)
• Refractive Index: 1.594
• Boiling Point: 277.8 °C at 760 mmHg
• PKA: pK1:10.03;pK2:11.62 (25°C)
• Flash Point: 140.2 °C
• PSA: 40.46000
• Density: 1.21 g/cm³
• LogP: 1.40620
• Storage Temp.: Store below +30°C.
• Solubility.: 77g/l
• Water Solubility.: 77 g/L (25 ºC)
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 124.052429494
• Heavy Atom Count: 9
• Complexity: 92.9

Purity/Quality:

99% ^*data from raw suppliers

Methylhydroquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: CC1=C(C=CC(=C1)O)O
• Uses: Antioxidant, polymerization inhibitor. Methylhydroquinone is used as stabilizer and antioxidant in aerylic monomers to prevent polymerization. Methylhydroquinone is a marine fungus metabolite, showing activity as an angiosupressor that interferes with the Akt pathway. Allows for screening of novel inhibitors of angiogenesis.

Technology Process of Methylhydroquinone

There total 117 articles about Methylhydroquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3-methyl-phenol (108-39-4) → 2-methylbenzene-1,4-diol (95-71-6,96937-50-7) + 2-Methyl-1,4-benzoquinone (553-97-9)

Guidance literature:

With dihydrogen peroxide; Ti-superoxide; In water; acetic acid; for 1.25h; Product distribution / selectivity; Heating / reflux;

Reference yield: 96.0%

ortho-cresol (95-48-7,77504-84-8) → 2-methylbenzene-1,4-diol (95-71-6,96937-50-7) + 2-Methyl-1,4-benzoquinone (553-97-9)

Guidance literature:

With dihydrogen peroxide; Ti-superoxide; In water; acetic acid; at 50 - 60 ℃; for 1.25h; Product distribution / selectivity; Heating / reflux;

Reference yield: 17.0%

ortho-cresol (95-48-7,77504-84-8) → 4-methyl resorcinol (496-73-1,73073-80-0) + 2-methylbenzene-1,4-diol (95-71-6,96937-50-7) + 2-methylbenzene-1,3-diol (608-25-3) + 3-methylbenzene-1,2-diol (488-17-5)

Guidance literature:

With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride; at -40 ℃; for 0.5h; Product distribution;

DOI:10.1039/c39800001128

upstream raw materials:

p-cresol

p-methylazidobenzene

2-methylmethoxybenzene

gentisyl alcohol

Downstream raw materials:

2,5-dimethoxy toluene

1,4-diethoxy-2-methyl-5-nitrobenzene

(2RS,4'R,8'R)-5-Methyl-tocol

(2RS,4'R,8'R)-7-Methyl-tocol

Refernces

• 1、 Bruns, David L.,Musaev, Djamaladdin G.,Stahl, Shannon S.. "Can Donor Ligands Make Pd(OAc)2a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria". supporting information. p. 19678 - 19688. Retrieved 2020/12/18.
• 2、 Wang, Hong-Shuang,Li, Hui-Jing,Wang, Long-Fei,Shen, Zhi-Lun,Wu, Yan-Chao. "Regioselective synthesis of gentisyl alcohol-type marine natural products". supporting information. p. 1891 - 1896. Retrieved 2018/05/29.