3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid

Base Information

• Chemical Name: 3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid
• CAS No.: 74609-46-4
• Molecular Formula: C9H10 Cl F3 O2
• Molecular Weight: 242.625
• European Community (EC) Number: 615-798-1
• DSSTox Substance ID: DTXSID401028724
• Nikkaji Number: J347.951J
• Wikidata: Q27119811
• Metabolomics Workbench ID: 56232
• Mol file: 74609-46-4.mol

Synonyms:74609-46-4;3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid;72748-35-7;3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid;3-(2-CHLORO-3,3,3-TRIFLUORO-1-PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID;cis-3-(2-Chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropanecarboxylic Acid;850227-76-8;(Z)-3-(2-Chloro-3,3,3-trifluoro-1-propenyl)2,2-dimethylcyclopropanecarboxylic Acid;3-(2-Chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylicacid;Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-;Tefluthrin (free acid);Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl inverted exclamation mark inverted exclamation mark inverted exclamation mark inverted exclamation mark;Cyclopropanecarboxylic acid,3-[(1Z)-2-chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethyl-, (1R,3R)-;C9-H10-Cl-F3-O2;tefluthrin TP;TFP acid;LAMBDA CYHALTHRIN ACID;SCHEMBL2353923;CHEBI:39319;SPVZAYWHHVLPBN-HYXAFXHYSA-N;DTXSID401028724;AKOS015962224;AC-1630;EN300-81908;A838177;Q27119811;(Z)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid;3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylic acid;3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane-1-carboxylic acid;3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethyl-1-cyclopropanecarboxylic acid;(1R,3R;1S,3S)-3-((Z)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid;3-[(Z)-2-chloranyl-3,3,3-tris(fluoranyl)prop-1-enyl]-2,2-dimethyl-cyclopropane-1-carboxylic acid

Chemical Property of 3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid

Chemical Property:

• PSA: 37.30000
• LogP: 3.02820
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 242.0321417
• Heavy Atom Count: 15
• Complexity: 320

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C1C(=O)O)C=C(C(F)(F)F)Cl)C
• Isomeric SMILES: CC1(C(C1C(=O)O)/C=C(/C(F)(F)F)\Cl)C
• Uses: Descyano-3-phenoxybenzyl Cyhalothrin is an impurity of Cyhaloythrin which is used as an insecticide.

Technology Process of 3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid

There total 8 articles about 3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-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: 84.0%

4-(1,1-Dichloro-2,2,2-trifluoro-ethyl)-6,6-dimethyl-3-oxa-bicyclo[3.1.0]hexan-2-one (107686-54-4,187592-70-7) → (+/-)-cis-3-<(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl>-2,2-dimethylcyclopropanecarboxylic acid (68086-36-2,68127-59-3,68127-60-6,68127-61-7,72257-63-7,72257-64-8,72748-35-7,72748-68-6,74111-94-7,74111-95-8,74609-46-4,76023-99-9,76647-97-7,82796-20-1,83212-82-2,87725-85-7,90129-56-9,104531-12-6,104531-15-9,122045-31-2,122406-91-1)

Guidance literature:

With zinc; In N,N-dimethyl-formamide; at 60 ℃; for 3h;

DOI:10.1016/S0040-4039(00)84469-X

Reference yield:

α-cyano-3-phenoxybenzyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (68085-85-8) → 3-(2-chloro-3,3,3-trifluoroprop-1-en-yl)-2,2-dimethylcyclopropanecarboxylic acid (74609-46-4) + 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile (39515-47-4)

Guidance literature:

With carboxylesterase EstSt₇ from Sulfolobus tokodaii strain 7; water; In ethanol; at 80 ℃; pH=9; Kinetics; Enzymatic reaction;

DOI:10.1016/j.molcatb.2013.07.022

Reference yield:

bifenthrin (92880-79-0,107497-60-9) → 3-(2-chloro-3,3,3-trifluoroprop-1-en-yl)-2,2-dimethylcyclopropanecarboxylic acid (74609-46-4) + (2-methyl-[1,1′-biphenyl]-3-yl)methanol (76350-90-8)

Guidance literature:

With carboxylesterase EstSt₇ from Sulfolobus tokodaii strain 7; water; In ethanol; at 80 ℃; pH=9; Kinetics; Enzymatic reaction;

DOI:10.1016/j.molcatb.2013.07.022

upstream raw materials:

α-cyano-3-phenoxybenzyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

bifenthrin

4-(1,1-Dichloro-2,2,2-trifluoro-ethyl)-6,6-dimethyl-3-oxa-bicyclo[3.1.0]hexan-2-one

ethyl (+/-)-cis,trans-3-<(E,Z)-2-chloro-3,3,3-trifluoroprop-1-enyl>-2,2-dimethylcyclopropanecarboxylate

Downstream raw materials:

cyhalothrin chloride

3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-[5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide

3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-[5-(2-chloro-4-nitrophenyl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide

3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide

Refernces

• 1、 Fujita,Kondo,Hiyama. "Practical, stereocontrolled synthesis of polyfluorinated artificial pyrethroids". . p. 4385 - 4394. Retrieved 2007/10/02.
• 2、 Engel, John F.,McPhail, Andrew T.,Miller, Richard W.. "Synthesis and X-Ray Crystal Structure of a New Potent Pyrethroid Acid, (+/-)-cis-3--2,2-dimethylcyclopropanecarboxylic Acid". . p. 1737 - 1740. Retrieved 2007/10/02.