trans-2-(Trifluoromethyl)cyclopropanecarboxylic acid

Base Information

• Chemical Name: trans-2-(Trifluoromethyl)cyclopropanecarboxylic acid
• CAS No.: 78376-99-5
• Molecular Formula: C₅H₅F₃O₂
• Molecular Weight: 154.089
• Hs Code.: 2916199590
• European Community (EC) Number: 807-832-0
• Nikkaji Number: J2.964.884K
• Mol file: 78376-99-5.mol

Synonyms:78376-99-5;TRANS-2-(TRIFLUOROMETHYL)CYCLOPROPANECARBOXYLIC ACID;1932455-67-8;(1R,2R)-2-(Trifluoromethyl)cyclopropanecarboxylic acid;(1R,2R)-2-(TRIFLUOROMETHYL)CYCLOPROPANE-1-CARBOXYLIC ACID;MFCD18027181;trans-2-(trifluoromethyl)cyclopropane-1-carboxylic acid;(+/-)-trans-2-(trifluoromethyl)cyclopropanecarboxylic acid;SCHEMBL24806528;GSNLYQDUCHEFFQ-PWNYCUMCSA-N;MFCD29048937;AKOS016015491;AT11287;AS-37506;CS-0170883;EN300-245139;EN300-268472;(1R,2R)-2-(Trifluoromethyl)cyclopropane-1-carboxylicacid;rac-(1R,2R)-2-(trifluoromethyl)cyclopropane-1-carboxylic acid;ABS-(1R,2R)-2-(TRIFLUOROMETHYL)CYCLOPROPANE-1-CARBOXYLIC ACID

Chemical Property of trans-2-(Trifluoromethyl)cyclopropanecarboxylic acid

Chemical Property:

• PSA: 37.30000
• LogP: 1.26940
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 154.02416388
• Heavy Atom Count: 10
• Complexity: 163

Purity/Quality:

98% ^*data from raw suppliers

trans-2-(Trifluoromethyl)cyclopropanecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C1C(F)(F)F)C(=O)O
• Isomeric SMILES: C1[C@H]([C@@H]1C(F)(F)F)C(=O)O

Technology Process of trans-2-(Trifluoromethyl)cyclopropanecarboxylic acid

There total 8 articles about trans-2-(Trifluoromethyl)cyclopropanecarboxylic 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: 70.0%

N-methoxy-N-methyl-2-(trifluoromethyl)cyclopropanecarboxamide → (±)-trans-2-(trifluoromethyl)cyclopropane-1-carboxylic acid (22581-33-5,78376-99-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; water; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1055/s-0031-1289711

Reference yield: 65.0%

ethyl 5,5,5-trifluoro-4-tosyloxyvalerate (94633-26-8) → (±)-trans-2-(trifluoromethyl)cyclopropane-1-carboxylic acid (22581-33-5,78376-99-5)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide;

Reference yield: 56.0%

((E)-2-((1RS,2SR)-2-(trifluoromethyl)cyclopropyl)vinyl)benzene → (±)-trans-2-(trifluoromethyl)cyclopropane-1-carboxylic acid (22581-33-5,78376-99-5)

Guidance literature:

With sodium periodate; ruthenium(III) trichloride hydrate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1021/ol200983s

upstream raw materials:

ethyl 5,5,5-trifluoro-4-tosyloxyvalerate

4-trifluoromethyl-4-oxobutyric acid ethyl ester

ethyl 5,5,5-trifluoro-4-oxo-3-ethoxycarbonyl-pentanoate

ethyl 4-hydroxy-5,5,5-trifluoropentanoate

Downstream raw materials:

trans-2-trifluoromethylcyclopropylmethanol

Toluene-4-sulfonic acid (1R,2R)-2-trifluoromethyl-cyclopropylmethyl ester

Refernces

• 1、 De Meijere, Armin,Kozhushkov, Sergei I.,Yufit, Dmitrii S.,Grosse, Christian,Kaiser, Marcel,Raev, Vitaly A.. "(2R,1'S,2'R)- And (2S,1'S,2'R)-3-[2-mono(di,tri)fluoromethylcyclopropyl] alanines and their incorporation into hormaomycin analogues". supporting information. p. 2844 - 2857. Retrieved 2015/02/19.
• 2、 Morandi, Bill,Cheang, Jeremy,Carreira, Erick M.. "Iron-catalyzed preparation of trifluoromethyl substituted vinyl- and alkynylcyclopropanes". supporting information; experimental part. p. 3080 - 3081. Retrieved 2011/08/04.