61820-11-9

Basic information

• Product Name: Cyclopropanecarbonitrile, 3-(2,2-dichloroethenyl)-2,2-dimethyl-
• Synonyms: Cyclopropanecarbonitrile, 3-(2,2-dichloroethenyl)-2,2-dimethyl-;3-(2,2-Dichloroethenyl)-2,2-diMethyl-cyclopropanecarbonitrile
• CAS NO: 61820-11-9
• Molecular Formula: C₈H₉Cl₂N
• Molecular Weight: 190
• EINECS: -0
• Mol File: 61820-11-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclopropanecarbonitrile, 3-(2,2-dichloroethenyl)-2,2-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarbonitrile, 3-(2,2-dichloroethenyl)-2,2-dimethyl-(61820-11-9)
• EPA Substance Registry System: Cyclopropanecarbonitrile, 3-(2,2-dichloroethenyl)-2,2-dimethyl-(61820-11-9)

Safety Data

• Hazardous Substances Data: 61820-11-9(Hazardous Substances Data)

Upstream product

• 65842-21-9 1-cyano-2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropanecarboxylic acid 
• 61863-97-6 3-bromo-1-cyano-2,2-dimethyl-5,5,5-trichloropentane 
• 3167-62-2 diethyl (dichloromethyl)phosphonate 
• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 67401-42-7 (+/-)-cis-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclopropanecarboxamide 
• 202519-14-0 2,2,4,6,6-pentachloro-3,3-dimethylhex-5-enoic acid nitrile 
• 60856-71-5 (+/-)-cis-cyanoaldehyde 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 2198-88-1 (+/-)-cis-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarbonitrile 
• 111455-25-5 Acetic acid (E)-5-cyano-1,1,4,4-tetramethyl-5-(2,4,6-trimethyl-benzenesulfonyl)-pent-2-enyl ester 
• 111455-27-7 (+/-)-cis-3-(2'methyl-1'-propenyl)-2,2-dimethyl-1-cyano-1-(2'-4'-6'-trimethyl-phenylsulfonyl)cyclopropane 

Downstream Products

• 55701-05-8 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 
• 59609-49-3 ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 63142-56-3 ethyl (+/-)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 51877-74-8 (1RS)-cis-permethrin 
• 59042-49-8 cis-permethrinic acid 
• 67401-42-7 (+/-)-cis-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclopropanecarboxamide 

Relevant articles and documents

Nitrile biotransformation for highly enantioselective synthesis of 3-substituted 2,2-dimethylcyclopropanecarboxylic acids and amides

Biotransformations of differently configured 2,2-dimethyl-3-substitued-cyclopropanecarbonitriles were studied using a nitrile hydratase/amidase-containing Rhodococcus sp. AJ270 whole-cell catalyst under very mild conditions. Although all of the cis-3-aryl-2,2-dimethylcyclopropanecarbonitriles appeared inert toward the biocatalyst, a number of racemic trans-isomers efficiently underwent a highly enantioselective hydrolysis to produce (+)-(1R,3R)-3-aryl-2,2-dimethylcyclopropanecarboxylic acids and (-)-(1S,3S)-3-aryl-2,2-dimethylcyclopropanecarboxamides in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of 1R-enantioselective nitrile hydratase and amidase, with the later being a dominant factor. The influence of the substrates on both reaction efficiency and enantioselectivity was discussed in terms of steric and electronic effects. Coupled with chemical transformations, biotransformations of nitriles provided convenient syntheses of optically pure geminally dimethyl-substituted cyclopropanecarboxylic acids and amides, including chrysanthemic acids, in both enantiomeric forms.

Synthesis of ethyl (+/-)-cis-3-(2,2-dihalogenovinyl)-2,2-dimethylcyclopropanecarboxylate

The two (+/-) cis pyrethroid ethyl esters 2a,b have been synthesized.These esters are obtained via stereoselective ScN' cyclization of 3b to 5b.Desulfonylation of 5b with retention of configuration at low temperature (Na/Hg, -30 deg C) affords (+/-)-cis-chrysanthemonitrile 6.This nitrile is converted into cis aldehyde 7 which by Wittig reaction provides pyrethroid nitriles 8a and 8b, respectively.Finally hydrolysis of the nitrile group gives the esters 2a and 2b in 30percent overall yield from 3b.

Preparation of cyano-substituted cyclopropane derivatives

A novel process is disclosed for the preparation of cyano-substituted cyclopropane derivatives of the following general formula: STR1 wherein R1, R2 and Hal have the meanings given in the description. The process comprises the steps of cyclizing and dehydrohalogenating, in the presence of a base, a 4,6,6,6-tetrahalo-2-cyano-3,3-dialkylhexanoic acid or an alkyl ester thereof, followed by thermal decarboxylation of the resulting cyclized and dehydrohalogenated product. Under selected conditions cyclization, dehydrohalogenation and decarboxylation occur simultaneously in one reaction zone. The resulting cyano-substituted cyclopropane derivatives are useful as intermediates in the production of insecticidally active compounds.