3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride

Base Information

• Chemical Name: 3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride
• CAS No.: 52314-67-7
• Deprecated CAS: 78491-05-1
• Molecular Formula: C8H9Cl3O
• Molecular Weight: 227.518
• European Community (EC) Number: 257-840-8
• DSSTox Substance ID: DTXSID1028027
• Nikkaji Number: J94.794F
• Mol file: 52314-67-7.mol

Synonyms:52314-67-7;3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride;Permethric chloride;3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride;EINECS 257-840-8;Cyclopropanecarbonyl chloride, 3-(2,2-dichloroethenyl)-2,2-dimethyl-;UNII-7433EG1ZY9;3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonylchloride;3-(2,2-Dichloroethenyl)-2,2-dmethylcyclopropanecarbonyl chloride;Cypermethric acid chloride;C8-H9-Cl3-O;C8H9Cl3O;SCHEMBL8409198;DTXSID1028027;7433EG1ZY9;3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropanecarbonyl chloride;MFCD00071724;AKOS015900508;AS-16149;LS-195517;FT-0652297;A829020;2,2-Dimethyl-3-(2,2-dichloroethenyl)cyclopropanecarbonyl chloride;2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarbonyl chloride;2,2-dimethyl-3-(dichlorovinyl)-cyclopropanecarboxylic acid chloride;2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropanecarbonyl chloride;2-(2,2-Dichlorovinyl)-3,3-dimethylcyclopropanecarbonyl chloride;3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxoyl chloride;3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride;2,2-dimethyl-3-(2',2'-dichloro-vinyl)-cyclopropanecarboxylic acid chloride;2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid chloride;2,2-dimethyl-3-(2,2-dichloroethenyl)cyclopropane carboxylic acid chloride;3-(2,2-dichloroethenyl)-2,2-dimethyl-1-cyclopropanecarbonyl chloride;3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid chloride

Chemical Property of 3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride

Chemical Property:

• Vapor Pressure: 0.0341mmHg at 25°C
• Refractive Index: 1.58
• Boiling Point: 242.4 °C at 760 mmHg
• Flash Point: 98.9 °C
• PSA: 17.07000
• Density: 1.424 g/cm³
• LogP: 3.34300
• Water Solubility.: 123.2mg/L at 25℃
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 225.971898
• Heavy Atom Count: 12
• Complexity: 241

Purity/Quality:

99.9% ^*data from raw suppliers

3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C1C(=O)Cl)C=C(Cl)Cl)C
• Uses: 3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride can be used as an important intermediate of pyrethroids to prepare pesticides such as permethrin, cypermethrin, beta-cypermethrin, pentenyl cypermethrin, etc.

Technology Process of 3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride

There total 11 articles about 3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarbonyl chloride 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: 96.1%

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (55701-05-8) → permethric acid chloride (52314-67-7)

Guidance literature:

With phosgene; triethylamine; at 100 ℃; for 2h;

Reference yield:

cis-permethrinic acid (59042-49-8) → (+/-)-cis-2-(2,2-dichloroethenyl)-3,3-dimethylcyclopropanecarboxylic acid chloride (52314-67-7,60254-21-9,61914-47-4,66182-41-0,66182-42-1,68539-75-3,69831-14-7,76984-70-8,77026-59-6)

Guidance literature:

With thionyl chloride; Heating;

Reference yield:

cis,trans methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate (61898-95-1) → (+/-)-cis-2-(2,2-dichloroethenyl)-3,3-dimethylcyclopropanecarboxylic acid chloride (52314-67-7,60254-21-9,61914-47-4,66182-41-0,66182-42-1,68539-75-3,69831-14-7,76984-70-8,77026-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH / ethanol; H₂O / Heating

2: SOCl₂, DMF / CHCl₃ / 3 h / 40 °C

With sodium hydroxide; thionyl chloride; N,N-dimethyl-formamide; In ethanol; chloroform; water;

DOI:10.1021/jf970408o

upstream raw materials:

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

(RS)-α-cyano-3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate

oxalyl dichloride

ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

Downstream raw materials:

N-perm-L-tyrosine methyl ester

(1S,3S)-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid phenethyl-amide

Refernces

• 1、 Butte, Werner,Kemper, Kerstin. "A spectrophotometric assay for pyrethroid-cleaving enzymes in human serum". . p. 49 - 53. Retrieved 1999.
• 2、 Shet,Shelar,Manvi. "Synthesis of new chiral and nonchiral pyrido [3,2-e],[1,3,4] oxadiazine derivatives". body text. p. 149 - 156. Retrieved 2011/01/03.
• 3、 Xue, Sijia,Guo, Yanling,Li, Jingzhi,Ke, Shaoyong,Duan, Liping. "Synthesis and biological activity of N′-(substituted pyrimidin-2-yl)-N-dichlorochrysanthemoyl thioureas and their fused heterocyclic compounds". . p. 262 - 264. Retrieved 2007/10/03.