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

Base Information

• Chemical Name: cis-3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid
• CAS No.: 68127-59-3
• Deprecated CAS: 76647-97-7
• Molecular Formula: C₉H₁₀ClF₃O₂
• Molecular Weight: 242.625
• European Community (EC) Number: 614-283-9,813-821-1,615-798-1
• DSSTox Substance ID: DTXSID70887168,DTXSID101335879
• Nikkaji Number: J483.205A,J922.922A
• Wikidata: Q76386748
• Mol file: 68127-59-3.mol

Synonyms:Lambda-cyhalothric acid;72748-35-7;68127-59-3;cis-3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid;cis-Cyhalothric acid;76023-99-9;(1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid;EC 614-283-9;C9H10ClF3O2;Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, cis-;(1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylic acid;(1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-cyclopropane-1-carboxylic acid;Cyclopropanecarboxylic acid, 3-((1Z)-2-chloro-3,3,3-trifluoro-1-propen-1-yl)-2,2-dimethyl-, (1R,3R)-rel-;C9-H10-Cl-F3-O2;Cyhalothric acid;Z-(1R,S)-cis-2,2-dimethyl-3-(2,2-chloro-3,3,3-trifluoro-1-propenyl)cyclopropanecarboxylic acid;(1R-cis)-Cyhalothric Acid;SCHEMBL2353926;DTXSID70887168;Cis-3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylicacid;DTXSID101335879;Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, (1a,3a(Z));MFCD04112623;AKOS015907709;BG-0206;CS-W008660;EN300-6734387;2,2-Dimethyl-3beta-(2-chloro-3,3,3-trifluoro-1-propenyl)cyclopropane-1beta-carboxylic acid;cis-3-[(2-Chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylic acid;(1R,3R)-3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propen-1-yl]-2,2-dimet hylcyclopropanecarboxylic acid;Cyclopropanecarboxylic acid,3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, (1R,3R)-rel-;rac-(1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylic acid

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

Chemical Property:

• Vapor Pressure: 0.009-1.218Pa at 20-59.9℃
• Melting Point: 109-111°C
• Boiling Point: 271.6°Cat760mmHg
• PKA: 4.01±0.42(Predicted)
• Flash Point: 118.1°C
• PSA: 37.30000
• Density: 1.449g/cm³
• LogP: 3.02820
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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:

99.9% ^*data from raw suppliers

(±)-Cyhalothric acid ^*data from reagent 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@H]([C@H]1C(=O)O)/C=C(/C(F)(F)F)\Cl)C
• Uses: (±)-Cyhalothric Acid is a useful reagent for the preparation of Tefluthrin (T013800(P)), which is a pyrethroid based insecticide. Tefluthrin is used in the control of a broad range of soil pests, including members of the Coleoptera, Lepidoptera, and Diptera.

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

There total 6 articles about cis-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:

2,2-dichloro-1,1,1-trifluoro-5-methyl-4-hexen-3-ol (103654-93-9) → (+/-)-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:

Multi-step reaction with 4 steps

1: 88 percent / sodium acetate / 4 h / 80 °C

2: 82 percent / triethylamine, tosyl azide, 1.2 M sodium hydroxide / acetonitrile; H₂O / 1.5 h / Ambient temperature

3: 75 percent / copper(II) acetylacetone / dioxane / 2.5 h / Heating

4: zinc / dimethylformamide / 3 h / 60 °C

With sodium hydroxide; 4-toluenesulfonyl azide; sodium acetate; triethylamine; zinc; copper acetylacetonate; In 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/bcsj.60.4385

Reference yield:

4-(2,4-dioxobutoxy)-5,5-dichloro-6,6,6-trifluoro-2-methyl-2-hexene (107686-52-2) → (+/-)-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:

Multi-step reaction with 3 steps

1: 82 percent / triethylamine, tosyl azide, 1.2 M sodium hydroxide / acetonitrile; H₂O / 1.5 h / Ambient temperature

2: 75 percent / copper(II) acetylacetone / dioxane / 2.5 h / Heating

3: zinc / dimethylformamide / 3 h / 60 °C

With sodium hydroxide; 4-toluenesulfonyl azide; triethylamine; zinc; copper acetylacetonate; In 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/bcsj.60.4385

upstream raw materials:

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

4-(1,1-dichloro-2,2,2-trifluoroethyl)-6,6-dimethyl-3-oxabicyclo<3.1.0>hexan-2-one

2,2-dichloro-1,1,1-trifluoro-5-methyl-4-hexen-3-ol

Refernces

• 1、 Fujita, Makoto,Hiyama, Tamejiro,Kondo, Kiyosi. "PRACTICAL AND STEREOCONTROLLED SYNTHESES OF BOTH (1R*,3S*)- AND (1R*,3R*)-3-(2-CHLORO-3,3,3-TRIFLUORO-1-PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATES". . p. 2139 - 2142. Retrieved 2007/10/02.