2,3-Dimethoxy-5-(chloromethyl)-6-methyl-1,4-benzoquinone

Base Information

• Chemical Name: 2,3-Dimethoxy-5-(chloromethyl)-6-methyl-1,4-benzoquinone
• CAS No.: 202843-56-9
• Molecular Formula: C10H11ClO4
• Molecular Weight: 230.648
• European Community (EC) Number: 606-488-7
• DSSTox Substance ID: DTXSID301159164
• Nikkaji Number: J1.704.032D
• Mol file: 202843-56-9.mol

Synonyms:SCHEMBL5082520;DTXSID301159164;2,3-Dimethoxy-5-(chloromethyl)-6-methyl-1,4-benzoquinone;5-chloromethyl-2,3-dimethoxy-6-me-thyl-1,4-benzoquinone;2-(Chloromethyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione;202843-56-9

Chemical Property of 2,3-Dimethoxy-5-(chloromethyl)-6-methyl-1,4-benzoquinone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 230.0345865
• Heavy Atom Count: 15
• Complexity: 379

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=O)C(=C(C1=O)OC)OC)CCl

Technology Process of 2,3-Dimethoxy-5-(chloromethyl)-6-methyl-1,4-benzoquinone

There total 14 articles about 2,3-Dimethoxy-5-(chloromethyl)-6-methyl-1,4-benzoquinone 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: 93.0%

2-hydroxymethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone (84055-96-9) → 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone (202843-56-9)

Guidance literature:

With N,N-dimethyl-formamide; phosphorus trichloride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ol051329y

Reference yield: 87.0%

1-(chloromethyl)-2,3,4,5-tetramethoxy-6-methylbenzene (127430-84-6) → 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone (202843-56-9)

Guidance literature:

With ammonium cerium (IV) nitrate; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.3184/174751911X13099411630089

Reference yield: 85.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2,3-Dimethoxy-5-methyl-1,4-benzoquinone (605-94-7) → 2,3-dimethoxy-5-chloro-6-methyl-1,4-benzoquinone (30685-16-6) + 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone (202843-56-9)

Guidance literature:

With hydrogenchloride; In water; toluene; at 0 - 20 ℃; for 3 - 10.5h;

upstream raw materials:

1-(chloromethyl)-2,3,4,5-tetramethoxy-6-methylbenzene

2-hydroxymethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone

2-hydroxymethyl-5,6-dimethoxy-3-methylphenol

2-hydroxy-3,4-dimethoxy-6-methylbenzaldehyde

Downstream raw materials:

ubiquinone ⁽²⁵⁾

ubiquinone Q₃

Ubichinon-7

ubiquinone 8

Refernces

• 1、 Wang, Jin,Li, Shuo,Yang, Tao,Yang, Jian. "Synthesis and antioxidant activities of Coenzyme Q analogues". . p. 710 - 713. Retrieved 2015/02/19.
• 2、 Wang, Jin,Yang, Jian,Zhou, Rong-Guang,Yang, Bo,Wu, Yuan-Shuang. "Alternative synthesis of 2-(4-benzoyl-piperazin-1-ylmethyl)-5, 6-dimethoxy-3-methyl-[1, 4]benzoquinone". experimental part. p. 431 - 432. Retrieved 2011/10/08.