1,4-Cyclohexadiene, 1-bromo-3,3,6,6-tetramethoxy-

Base Information

• Chemical Name: 1,4-Cyclohexadiene, 1-bromo-3,3,6,6-tetramethoxy-
• CAS No.: 60316-51-0
• Molecular Formula: C10H15BrO4
• Molecular Weight: 279.131
• DSSTox Substance ID: DTXSID20439010
• Nikkaji Number: J775.316K
• Mol file: 60316-51-0.mol

Synonyms:1-Bromo-3,3,6,6-tetramethoxy-1,4-cyclohexadiene;60316-51-0;1,4-Cyclohexadiene, 1-bromo-3,3,6,6-tetramethoxy-;DTXSID20439010

Chemical Property of 1,4-Cyclohexadiene, 1-bromo-3,3,6,6-tetramethoxy-

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 278.01537
• Heavy Atom Count: 15
• Complexity: 277

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1(C=CC(C(=C1)Br)(OC)OC)OC

Technology Process of 1,4-Cyclohexadiene, 1-bromo-3,3,6,6-tetramethoxy-

There total 2 articles about 1,4-Cyclohexadiene, 1-bromo-3,3,6,6-tetramethoxy- 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: 87.0%

methanol (67-56-1) + 1-bromo-2,5-dimethoxybenzene (25245-34-5) → 2-bromo-1,1,4,4-tetramethoxycyclohexa-2,5-diene (60316-51-0)

Guidance literature:

With potassium hydroxide; at -7 ℃; for 16h; anodic oxidation;

DOI:10.1016/0022-328X(90)85125-I

Reference yield:

→ 2-bromo-1,1,4,4-tetramethoxycyclohexa-2,5-diene (60316-51-0)

Guidance literature:

2-Brom-1,4-dimethoxybenzol, anodische Oxidation / Methanol;

DOI:10.1021/ja00432a049

Reference yield: 90.0%

2-bromo-1,1,4,4-tetramethoxycyclohexa-2,5-diene (60316-51-0) + tert.-butyl lithium (594-19-4) + chromium(0) hexacarbonyl (199620-14-9,13007-92-6) → lithium(pentacarbonyl(1,1,4,4,-tetramethoxycyclohexa-2,5-diene)chromate)

Guidance literature:

In diethyl ether; under dry inert gas, addn. of a suspn. of t-BuLi (hexane) to a soln. of the bromide in ether, -75°C, stirring 10 h (orange suspn.), addn. of the suspn.to a suspn. of Cr(CO)6 in ether, -60°C, warming to room temp. during 4 h; vac. evapn., residue washed (pentane), dried;

upstream raw materials:

methanol

1-bromo-2,5-dimethoxybenzene

Downstream raw materials:

2-(7-Hydroxybicyclo<4.2.0>octa-1,3,5-trien-7-yl)-p-benzoquinone, Bis(dimethyl acetal)

2-o-Toluyl-p-benzoquinone, Bis(dimethyl acetal)

3,3,6,6-Tetramethoxy-1-methylsulfanyl-cyclohexa-1,4-diene

[S(S)]-2-p-tolylsulfinyl-1,1,4,4-tetramethoxy-2,5-cyclohexadiene

Refernces

• 1、 Gautier, Elisabeth C. L.,Lewis, Norman J.,McKillop, Alexander,Taylor, Richard J. K.. "Synthesis of bromoxone". . p. 8759 - 8760. Retrieved 2007/10/02.
• 2、 Henton, Daniel R.,McCreery, Richard L.,Swenton, John S.. "Anodic Oxidation of 1,4-Dimethoxy Aromatic Compounds. A Facile Route to Functionalized Quinone Bisketals.". . p. 369 - 378. Retrieved 2007/10/02.