Dimethyl benzyl(trifluoromethyl)propanedioate

Base Information

• Chemical Name: Dimethyl benzyl(trifluoromethyl)propanedioate
• CAS No.: 86311-86-6
• Molecular Formula: C13H13F3O4
• Molecular Weight: 290.239
• DSSTox Substance ID: DTXSID90513997
• Wikidata: Q82374065
• Mol file: 86311-86-6.mol

Synonyms:Dimethyl benzyl(trifluoromethyl)propanedioate;86311-86-6;DTXSID90513997

Chemical Property of Dimethyl benzyl(trifluoromethyl)propanedioate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 290.07659338
• Heavy Atom Count: 20
• Complexity: 343

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=CC=C1)(C(=O)OC)C(F)(F)F

Technology Process of Dimethyl benzyl(trifluoromethyl)propanedioate

There total 3 articles about Dimethyl benzyl(trifluoromethyl)propanedioate 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: 45.0%

methyl dimethyl 2-(trifluoromethyl)propanedioate (5838-00-6) + benzyl bromide (100-39-0) → dimethyl benzyl(trifluoromethyl)malonate (86311-86-6)

Guidance literature:

With cesium fluoride; In diethylene glycol dimethyl ether; at 70 - 75 ℃; for 0.833333h;

DOI:10.1246/bcsj.56.724

Reference yield:

1,1,1,3,3-pentafluoro-3-methoxy-2-trifluoromethylpropane (382-26-3) → dimethyl benzyl(trifluoromethyl)malonate (86311-86-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) triethylamine, 2.) conc. H₂SO₄ / 1.) DMF, from 10 to 20 deg C, 2.) ether, RT, overnight

2: 45 percent / CsF / bis-(2-methoxy-ethyl) ether / 0.83 h / 70 - 75 °C

With sulfuric acid; triethylamine; cesium fluoride; In diethylene glycol dimethyl ether;

DOI:10.1246/bcsj.56.724

Reference yield:

benzyl bromide (100-39-0) + 3,3,3-Trifluoro-1-methoxy-2-methoxycarbonyl-propan-1-olatetetraethyl-ammonium; → dimethyl benzyl(trifluoromethyl)malonate (86311-86-6)

Guidance literature:

In N,N-dimethyl-formamide; Yield given;

DOI:10.1021/jo00232a041

upstream raw materials:

methyl dimethyl 2-(trifluoromethyl)propanedioate

benzyl bromide

1,1,1,3,3-pentafluoro-3-methoxy-2-trifluoromethylpropane

Refernces

• 1、 Ishikawa, Nobuo,Yokozawa, Tsutomu. "Convenient Preparation of Dimethyl (Trifluoromethyl)malonate and Related Compounds". . p. 724 - 726. Retrieved 2007/10/02.