Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, trans-

Base Information

• Chemical Name: Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, trans-
• CAS No.: 72748-68-6
• Molecular Formula: C₉H₁₀ClF₃O₂
• Molecular Weight: 242.625
• European Community (EC) Number: 615-798-1
• Nikkaji Number: J483.207H
• Mol file: 72748-68-6.mol

Synonyms:72748-68-6;Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, trans-;(1R,3S)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid;trans-3-(2-Chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropanecarboxylic Acid;C9-H10-Cl-F3-O2;SCHEMBL6423603;SCHEMBL6423605;SPVZAYWHHVLPBN-FAAOWNOOSA-N;72748-35-7;A837604;(1R,3R)-rel-3-(2-Chloro-3,3,3-trifluoro-1-propenyl)-2,2-diMethyl-cyclopropanecarboxylic Acid;cis-3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid;(1R,3S)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylic acid;2,2-Dimethyl-3alpha-(2-chloro-3,3,3-trifluoro-1-propenyl)cyclopropane-1beta-carboxylic acid

Chemical Property of Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, trans-

Chemical Property:

• Vapor Pressure: 0.00179mmHg at 25°C
• Melting Point: 109 - 112°C
• Boiling Point: 271.6°C at 760 mmHg
• PKA: 4.18±0.33(Predicted)
• Flash Point: 118.1°C
• PSA: 37.30000
• Density: 1.449g/cm³
• LogP: 3.02820
• Storage Temp.: Refrigerator
• Solubility.: Acetone (Slightly), Chloroform (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:

trans-3-(2-Chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropanecarboxylicAcid ^*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: trans-3-(2-Chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropanecarboxylic Acid is a reagent used in the synthesis of indanyl insecticides.

Technology Process of Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, trans-

There total 6 articles about Cyclopropanecarboxylic acid, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-, trans- 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.