Ethyl 1-(trifluoromethyl)cyclopropanecarboxylate

Base Information

• Chemical Name: Ethyl 1-(trifluoromethyl)cyclopropanecarboxylate
• CAS No.: 139229-57-5
• Molecular Formula: C7H9F3O2
• Molecular Weight: 182.142
• Hs Code.: 2916200090
• DSSTox Substance ID: DTXSID70566709
• Wikidata: Q82452454
• Mol file: 139229-57-5.mol

Synonyms:Ethyl 1-(trifluoromethyl)cyclopropanecarboxylate;139229-57-5;Ethyl 1-(trifluoromethyl)cyclopropane-1-carboxylate;Cyclopropanecarboxylic acid, 1-(trifluoromethyl)-, ethyl ester;Ethyl 1-Trifluoromethylcyclopropanecarboxylate;MFCD22199506;Ethyl1-(trifluoromethyl)cyclopropanecarboxylate;SCHEMBL9313190;AMY3066;DTXSID70566709;XKNRIQDQYMPZKZ-UHFFFAOYSA-N;BCP05937;AKOS015998762;PB48556;DS-18204;SY105084;CS-0054279;EN300-85985;A854689

Chemical Property of Ethyl 1-(trifluoromethyl)cyclopropanecarboxylate

Chemical Property:

• Boiling Point: 127.4±35.0 °C(Predicted)
• PSA: 26.30000
• Density: 1.311±0.06 g/cm3(Predicted)
• LogP: 1.89200
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 182.05546401
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

98% ^*data from raw suppliers

Ethyl1-Trifluoromethylcyclopropanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CC1)C(F)(F)F
• Uses: Ethyl 1-Trifluoromethylcyclopropanecarboxylate is used prepare fungicidal/pesticidal benzyl cyclopropanecarboxylates.

Technology Process of Ethyl 1-(trifluoromethyl)cyclopropanecarboxylate

There total 4 articles about Ethyl 1-(trifluoromethyl)cyclopropanecarboxylate 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: 76.0%

sulfur tetrafluoride + 1,1-cyclopropanedicarboxylic acid monoethyl ester (3697-66-3) + chromium (7440-47-3) + nickel (7440-02-0) + molybdenum (7439-98-7) → ethyl 1-(trifluoromethyl)cyclopropane-1-carboxylate (139229-57-5)

Guidance literature:

With hydrogen fluoride; In dichloromethane;

Reference yield: 54.0%

1,1-cyclopropanedicarboxylic acid monoethyl ester (3697-66-3) → ethyl 1-(trifluoromethyl)cyclopropane-1-carboxylate (139229-57-5)

Guidance literature:

With sulfur tetrafluoride; water; for 24h; Autoclave;

DOI:10.1021/acs.joc.9b02596

Reference yield:

diethyl cyclopropane-1,1-dicarboxylate (1559-02-0) → ethyl 1-(trifluoromethyl)cyclopropane-1-carboxylate (139229-57-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 71.6 percent / KOH / ethanol / 6 h / 25 °C

2: SF₄ / 21 h / 60 °C

With potassium hydroxide; sulfur tetrafluoride; In ethanol; 1: Saponification / 2: Substitution;

DOI:10.1016/S0022-1139(00)00257-8

upstream raw materials:

1,1-cyclopropanedicarboxylic acid monoethyl ester

diethyl cyclopropane-1,1-dicarboxylate

chromium

nickel

Downstream raw materials:

2-(4-(6-aminopyridin-3-yl)-2-fluorophenyl)-N-(5-(1-(trifluoromethyl)cyclopropyl)isoxazol-3-yl)acetamide

Refernces

• 1、 Hell,Finta,Dmowski,Faigl,Pustovit,Toke,Harmat. "Reaction of cyclopropane carboxylic acid derivatives with sulphur tetrafluoride - An example of a diastereoselective ring opening". . p. 297 - 301. Retrieved 2007/10/03.