Trimethylhydroquinone

Base Information

• Chemical Name: Trimethylhydroquinone
• CAS No.: 700-13-0
• Molecular Formula: C9H12O2
• Molecular Weight: 152.193
• Hs Code.: Oral rat LD50: 3200 mg/kg
• European Community (EC) Number: 211-838-3
• NSC Number: 401617
• UNII: GSY6340N4A
• DSSTox Substance ID: DTXSID7052446
• Nikkaji Number: J12.289K
• Wikidata: Q27279264
• Metabolomics Workbench ID: 130602
• ChEMBL ID: CHEMBL3182864
• Mol file: 700-13-0.mol

Synonyms:Hydroquinone,trimethyl- (6CI,7CI,8CI);1,4-Dihydroxy-2,3,5-trimethylbenzene;2,3,5-Trimethyl-1,4-benzenediol;2,3,5-Trimethyl-1,4-hydroquinone;2,3,5-Trimethyl-p-hydroquinone;2,3,5-Trimethylhydroquinone;NSC 401617;Pseudocumohydroquinone;Trimethyl-p-hydroquinone;Trimethylhydroquinone;y-Cumohydroquinone;

Chemical Property of Trimethylhydroquinone

Chemical Property:

• Appearance/Colour: off-white, tan or orange powder
• Vapor Pressure: 0.000723mmHg at 25°C
• Melting Point: 169-174 °C
• Refractive Index: 1.572
• Boiling Point: 298.3 °C at 760 mmHg
• PKA: 11.28±0.28(Predicted)
• Flash Point: 146.3 °C
• PSA: 40.46000
• Density: 1.126 g/cm³
• LogP: 2.02300
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: 2 g/L (20 ºC)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 152.083729621
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

98%, ^*data from raw suppliers

Trimethylhydroquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; N
• Hazard Codes: Xn,N
• Statements: 20-37/38-41-43-50/53
• Safety Statements: 24-26-37/39-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: CC1=CC(=C(C(=C1O)C)C)O
• Uses: The product is main ring of vitamin E, it can condensation with isophytol to get vitamin E. Organic intermediates, pharmaceutical intermediates, it can be used for the synthesis of VE. Trimethylhydroquinone is used for synthesizing vitamin E and used as medical intermediate. Trimethylhydroquinone is a key precursor for the synthesis of tocopherols (vitamin E) and (±)-madindolines.
• Production method: By sulfonation, nitration, reduction, oxidation 1,2,4-trimethylbenzene can get 2,3,5-trimethyl benzoquionone ([935-92-2]). 2,3,5-trimethyl benzoquionone is yellow needle crystallization, melting point is 32℃ (38-29.5℃), the boiling point is 53℃(53Pa). Said step of products are generally to obtain a solution of petroleum ether or gasoline. In 2,3,5-trimethyl gasoline solution (petroleum ether), hydrosulfite solution is added with stirring, stir at room temperature for 3h, then filter, the cake should be washed with 0.5% hydrosulfite solution, and then dry to get trimethyl hydroquinone.

Technology Process of Trimethylhydroquinone

There total 42 articles about Trimethylhydroquinone 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: 100.0%

2,3,5-Trimethyl-1,4-benzoquinone (935-92-2) → Trimethylhydroquinone (700-13-0)

Guidance literature:

With sodium dithionite; In diethyl ether; water;

Reference yield: 94.7%

2-Bromo-3,5,6-trimethyl-1,4-benzoquinone (7210-68-6) → Trimethylhydroquinone (700-13-0)

Guidance literature:

With hydrogen; sodium carbonate; at 80 ℃;

Reference yield: 88.5%

2,6,6-trimethyl-1,4-cyclohexanedione (20547-99-3) + acetic anhydride (108-24-7) → Trimethylhydroquinone (700-13-0) + trimethylpyrocatechol (3938-10-1)

Guidance literature:

2,6,6-trimethyl-1,4-cyclohexanedione; acetic anhydride; With sulfuric acid; acetic acid; at 50 ℃; for 2h;

With water; for 3h; Heating / reflux;

upstream raw materials:

2,3,5-Trimethyl-1,4-benzoquinone

2-(2,4,6-trimethylphenyl)quinoline

4-Hexadecyloxy-2,3,6-trimethyl-phenol

peracetic acid

Downstream raw materials:

3,5,6,3',5',6'-hexamethyl-2,2'-methanediyl-di-hydroquinone

2-chloromethyl-3,5,6-trimethyl-hydroquinone

1,4-diethoxy-2,3,5-trimethyl-benzene

2,3,5-Trimethyl-1,4-benzoquinone

Refernces

• 1、 Cai, Xiaoxiong,Pan, Jianping,Tu, Gaomei,Fu, Yanghe,Zhang, Fumin,Zhu, Weidong. "Pd/UiO-66(Hf): A highly efficient heterogeneous catalyst for the hydrogenation of 2,3,5-trimethylbenzoquinone". . p. 23 - 26. Retrieved 2018.
• 2、 -. "PROCESS FOR THE PREPARATON OF HYDROQUINONES". Page/Page column 10. . Retrieved 2021/06/26.
• 3、 -. "FORMATION OF 2,3,5-TRIMETHYLHYDROQUINONE FROM 2,3,6-TRIMETHYLPHENOL". Page/Page column 12; 13. . Retrieved 2021/06/26.