1,4-Dimethyl 2,5-bis(bromomethyl)-1,4-benzenedicarboxylate

Base Information

• Chemical Name: 1,4-Dimethyl 2,5-bis(bromomethyl)-1,4-benzenedicarboxylate
• CAS No.: 54100-54-8
• Molecular Formula: C₁₂H₁₂Br₂O₄
• Molecular Weight: 380.033
• European Community (EC) Number: 684-425-2
• DSSTox Substance ID: DTXSID401194111
• Mol file: 54100-54-8.mol

Synonyms:54100-54-8;SCHEMBL19691966;DTXSID401194111;AKOS024428631;1,4-Dimethyl 2,5-bis(bromomethyl)-1,4-benzenedicarboxylate

Chemical Property of 1,4-Dimethyl 2,5-bis(bromomethyl)-1,4-benzenedicarboxylate

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 379.90818
• Heavy Atom Count: 18
• Complexity: 279

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=C(C=C1CBr)C(=O)OC)CBr

Technology Process of 1,4-Dimethyl 2,5-bis(bromomethyl)-1,4-benzenedicarboxylate

There total 5 articles about 1,4-Dimethyl 2,5-bis(bromomethyl)-1,4-benzenedicarboxylate 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: 85.0%

2,5-dimethylterephthalic acid, dimethyl ester (54100-53-7) → dimethyl 2,5-bis(bromomethyl)benzene-1,4-dicarboxylate (54100-54-8)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In dichloromethane; for 2h; Reflux;

DOI:10.1021/jo801441h

Reference yield:

2,5-dimethylterephthalic acid (6051-66-7) → dimethyl 2,5-bis(bromomethyl)benzene-1,4-dicarboxylate (54100-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1: MeSO₃H / 10 h / Heating

2: 42 percent / NBS, benzoyl peroxide / CCl₄ / 21 h / Heating

With N-Bromosuccinimide; Perbenzoic acid; methanesulfonic acid; In tetrachloromethane;

DOI:10.1021/ja982499r

Reference yield:

2,5-dibromo-p-xylene (1074-24-4) → dimethyl 2,5-bis(bromomethyl)benzene-1,4-dicarboxylate (54100-54-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / dimethylformamide / 48 h / Heating

2: KOH / bis-(2-hydroxy-ethyl) ether / Heating

3: MeSO₃H / 10 h / Heating

4: 42 percent / NBS, benzoyl peroxide / CCl₄ / 21 h / Heating

With potassium hydroxide; N-Bromosuccinimide; Perbenzoic acid; methanesulfonic acid; In tetrachloromethane; N,N-dimethyl-formamide; diethylene glycol;

DOI:10.1021/ja982499r

upstream raw materials:

2,5-dimethylterephthalic acid, dimethyl ester

2,5-dimethylbenzene-1,4-dicarbonitrile

2,5-dimethylterephthalic acid

2,5-dibromo-p-xylene

Downstream raw materials:

C₄₀H₄₀O₈S₂

C₃₈H₃₆O₆S₂

14,17-Bis(benzyloxycarbonylamino)<3.3>paracyclophan-5,8-diacetonitril

N,N'-Bis(benzyloxycarbonyl)<3.3>paracyclophan-5,8-diamin