Cyclopropanecarbonyl chloride, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-

Base Information

• Chemical Name: Cyclopropanecarbonyl chloride, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-
• CAS No.: 69831-14-7
• Deprecated CAS: 71748-93-1,80184-11-8,80184-11-8
• Molecular Formula: C8H9Cl3O
• Molecular Weight: 227.518
• DSSTox Substance ID: DTXSID5074925
• Mol file: 69831-14-7.mol

Synonyms:Cyclopropanecarbonyl chloride, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-;69831-14-7;C8-H9-Cl3-O;SCHEMBL8407543;DTXSID5074925;CHLAOFANYRDCPD-NJGYIYPDSA-N;(1R)-cis-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarbonyl chloride

Chemical Property of Cyclopropanecarbonyl chloride, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-

Chemical Property:

• Vapor Pressure: 0.034mmHg at 25°C
• PSA: 17.07000
• LogP: 3.34300
• 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:

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
• Isomeric SMILES: CC1([C@H]([C@H]1C(=O)Cl)C=C(Cl)Cl)C

Technology Process of Cyclopropanecarbonyl chloride, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-

There total 5 articles about Cyclopropanecarbonyl chloride, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)- 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:

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

Reference yield:

trans-permethrin acid (55667-40-8,55701-03-6,55701-05-8,55701-06-9,55701-07-0,55701-08-1,55701-09-2,59042-49-8,59042-50-1) → (+/-)-trans-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;

upstream raw materials:

trans-permethrin acid

cis,trans methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate

cis-permethrinic acid

Downstream raw materials:

N-perm-L-tyrosine methyl ester

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

(+)-(S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate

Refernces

• 1、 Ahn, Ki Chang,Watanabe, Takaho,Gee, Shirley J.,Hammock, Bruce D.. "Hapten and antibody production for a sensitive immunoassay determining a human urinary metabolite of the pyrethroid insecticide permethrin". . p. 4583 - 4594. Retrieved 2007/10/03.
• 2、 Zou, Xinzhuo,Qiu, Zongxing. "Syntheses of 4-methoxymethylbenzyl permethrinates containing fluorine and their insecticidal activity". . p. 173 - 179. Retrieved 2007/10/03.