3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid

Base Information

• Chemical Name: 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid
• CAS No.: 59952-39-5
• Molecular Formula: C₈H₁₀Br₂O₂
• Molecular Weight: 297.974
• Mol file: 59952-39-5.mol

Synonyms:2-(2,2-dibromovinyl)-3,3-dimethyl-cyclopropanecarboxylic acid;2,2-dimethyl-3-(2',2'-dibromovinyl)-cyclopropanecarboxylic acid;(1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethyl-cyclopropane carboxylic acid;(+-)-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid;2,2-dimethyl-3-(2,2-dibromo-1-ethenyl)cyclopropanecarboxylic acid ester;3-(2,2-dibromoethenyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid;

Chemical Property of 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 326.351°C at 760 mmHg
• PKA: 4.09±0.33(Predicted)
• Flash Point: 151.172°C
• PSA: 37.30000
• Density: 1.994g/cm³
• LogP: 2.97440

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid

There total 65 articles about 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid 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: 86.0%

6,6-dimethyl-4(R)-tribromomethyl-3-oxa-bicyclo(3,1,0)hexan-2-one (72345-90-5) + zinc (7440-66-6) → 3-(2',2'-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid (53179-78-5,61914-48-5,63538-10-3,63597-73-9,63949-77-9,72691-16-8,72691-18-0,74560-76-2,59952-39-5)

Guidance literature:

In water; acetic acid;

Reference yield: 60.0%

3-(2',2'-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid (53179-78-5,61914-48-5,63538-10-3,63597-73-9,63949-77-9,72691-16-8,72691-18-0,74560-76-2,59952-39-5) → 2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid (53179-78-5,59952-39-5,61914-48-5,63538-10-3,63597-73-9,63949-77-9,72691-16-8,72691-18-0,74560-76-2) + cis-(1S,3R)-Deltamethrinic acid (72691-18-0) + D,L-trans 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acid (61914-48-5) + (1S,3R)-3-(2',2'-Dibromvinyl)-2,2-dimethylcyclopropancarbonsaeure

Guidance literature:

3-(2',2'-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid; With Tentagel resin;

With lipase enzyme; In tetrahydrofuran; tert-butyl alcohol; at 30 ℃; for 8h; pH=7.8;

DOI:10.1016/S0040-4039(99)01127-2

Reference yield: 55.0%

deltametrin (52918-63-5) → 3-(2',2'-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid (53179-78-5,61914-48-5,63538-10-3,63597-73-9,63949-77-9,72691-16-8,72691-18-0,74560-76-2,59952-39-5) + 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile (39515-47-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 72h; Heating;

DOI:10.1021/jf970438r

upstream raw materials:

6,6-dimethyl-4(R)-tribromomethyl-3-oxa-bicyclo(3,1,0)hexan-2-one

deltametrin

zinc

1-chloro-3,3-dimethyl-pent-4-en-2-one

Downstream raw materials:

(1S,3S)-3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid; compound with furan

(1S,3S)-3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid; compound with 2-methyl-furan

(1S,3S)-3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid; compound with benzene

2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid

Refernces

• 1、 Krief, Alain,Jeanmart, Stéphane,Gondal, Humaira Y.,Kremer, Adrian. "Syntheses of racemic and scalemic cis-chrysanthemic acid from β,γ-unsaturated cyclohexanol". . p. 2123 - 2167. Retrieved 2013/02/23.
• 2、 Krief, Alain,Jeanmart, Stephane,Kremer, Adrian. "Diastereoselective bromination of compounds bearing a cyclohex-3-enol moiety: Application to the enantioselective synthesis of (1R)-cis-deltamethrinic acid". experimental part. p. 9795 - 9797. Retrieved 2009/04/07.