371-27-7

Basic information

• Product Name: 2,2,2-TRIFLUOROETHYL BUTYRATE
• Synonyms: 2,2,2-TRIFLUOROETHYL N-BUTYRATE;2,2,2-TRIFLUOROETHYL BUTYRATE;N-BUTYRIC ACID 2,2,2-TRIFLUOROETHYL ESTER;Butyric acid, TFE;2,2,2-Trifluoroethyl butyrate 98%;2,2,2-Trifluoroethylbutyrate98%;Butyric Acid 2,2,2-Trifluoroethyl Ester;Butanoic acid, 2,2,2-trifluoroethyl ester
• CAS NO: 371-27-7
• Molecular Formula: C₆H₉F₃O₂
• Molecular Weight: 170.13
• Product Categories: C6 to C7;Carbonyl Compounds;Esters
• Mol File: 371-27-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 113 °C747 mm Hg(lit.)
• Flash Point: 75 °F
• Appearance: /
• Density: 1.127 g/mL at 25 °C(lit.)
• Vapor Pressure: 32.4mmHg at 25°C
• Refractive Index: n20/D 1.347(lit.)
• BRN: 1769212
• CAS DataBase Reference: 2,2,2-TRIFLUOROETHYL BUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRIFLUOROETHYL BUTYRATE(371-27-7)
• EPA Substance Registry System: 2,2,2-TRIFLUOROETHYL BUTYRATE(371-27-7)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3272 3/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 371-27-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

InChI:InChI=1/C6H9F3O2/c1-2-3-5(10)11-4-6(7,8)9/h2-4H2,1H3

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 141-75-3 butyryl chloride 
• 107-92-6 butyric acid 
• 2635-84-9 p-nitrophenyl butyrate 
• 106-31-0 butanoic acid anhydride 
• 67696-25-7 bis(2,2,2-trifluoroethoxy)triphenylphosphorane 

Downstream Products

• 176966-03-3 1-O-butanoyl-2-O-β-D-glucopyranosyl-sn-glycerol 
• 35677-83-9 methyl (S)-pipecolinate 
• 35677-83-9 (+)-2R-Piperidine-2-carboxylic acid methyl ester 
• 831171-99-4 N-[2-hydroxy-2-(4-hydroxy-phenyl)-ethyl]-butyramide 
• 960403-29-6 (S)-4,4-diphenyl-3-buten-2-yl butanoate 

Relevant articles and documents

Lipase-catalyzed kinetic resolution of 7-, 8- and 12-membered alicyclic β-amino esters and N-hydroxymethyl-β-lactam enantiomers

Enzymatic kinetic resolutions of methyl cis-2-aminocycloheptane-, 2-aminocyclooctane- and 2-aminocyclododecanecarboxylates with Candida antarctica lipase A in diisopropyl ether (E >200) and of the corresponding N-hydroxymethyl-β-lactams with Pseudomonas cepacia lipase in dry acetone (E from 27 to >200) has been performed with 2,2,2-trifluoroethyl butanoate as the best acyl donor, with both enantiomers being obtained. trans-13-Hydroxymethyl-13-azabicyclo[10.2.0]tetradecan-14-one was resolved with vinyl butanoate and Candida antarctica lipase B (E=26) in acetone.

Lipase-catalyzed kinetic resolution of 2-aminocyclopentane- and 2-aminocyclohexanecarboxamides

Candida antarctica lipase B (CAL-B)-catalyzed N-acylation with 2,2,2-trifluoroethyl butanoate in solvent mixtures of tert-butyl methyl ether and tert-amyl alcohol was used to prepare all the enantiomers of cis- and trans-2-aminocyclopentane- and -cyclohexanecarboxamides. An unexpected change in enantiopreference, accompanied by low enantioselectivity, was observed when Pseudomonas cepacia lipase (cis-cyclohexane substrate) or C. antarctica lipase A (cis-cyclopentane and -cyclohexane substrates) replaced CAL-B.

Enantioselective synthesis of a hindered furyl substituted allyl alcohol intermediate: A case study in asymmetric synthesis

In the course of the synthesis of the DEFG ring system of cneorin C 1, we were faced with the task of preparing the furyl substituted allyl alcohol 5 enantioselectively. Several different methods starting from enantioselective zinc-mediated alkylations were attempted, but none of them proved entirely satisfactory. The solution turned out to be enzymatic kinetic resolution through a highly enantioselective (E>300) acylation in the presence of Candida antarctica lipase A.