130025-34-2

Basic information

• Product Name: 1,1,1-TRIFLUORO-2,3-EPOXYPROPANE
• Synonyms: 1,2-EPOXY-3,3,3-TRIFLUOROPROPANE;2-(TRIFLUOROMETHYL)OXIRANE;(S)-2-(Trifluoromethyl)oxirane,Trifluoropropeneoxide;(S)-3,3,3-Trifluoro-1,2-epoxypropane99%;(2S)-3,3,3-Trifluoro-1,2-propenoxide 99%;(2S)-2-(Trifluoromethyl)oxirane;(2S)-2-(Trifluoromethyl)oxirane, (2S)-3,3,3-Trifluoro-1,2-epoxypropane;rac-2-(Trifluoromethyl)oxirane
• CAS NO: 130025-34-2
• Molecular Formula: C₃H₃F₃O
• Molecular Weight: 112.05
• Mol File: 130025-34-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: -80
• Boiling Point: 40
• Flash Point: -21.5
• Appearance: /
• Density: 1.3068
• Vapor Pressure: 560mmHg at 25°C
• Refractive Index: n20/D <1.300
• Storage Temp.: ?20°C
• CAS DataBase Reference: 1,1,1-TRIFLUORO-2,3-EPOXYPROPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1-TRIFLUORO-2,3-EPOXYPROPANE(130025-34-2)
• EPA Substance Registry System: 1,1,1-TRIFLUORO-2,3-EPOXYPROPANE(130025-34-2)

Safety Data

• Hazard Codes: F,F+
• Statements: 12
• Safety Statements: 3
• RIDADR: UN 1993 3/PG 1
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 130025-34-2(Hazardous Substances Data)

Usage

Uses

Precursor to a trifluoromethyl chiral auxiliary which promotes a highly diastereoselective Simmons-Smith cyclopropanation.

InChI:InChI=1/C3H3F3O/c4-3(5,6)2-1-7-2/h2H,1H2/t2-/m0/s1

Upstream product

• 359-41-1 1,1,1-trifluoro-2,3-epoxypropane 
• 137429-44-8 3-bromo-1,1,1-trifluoropropan-2-ol 
• 431-35-6 3-bromo-1,1,1-trifluoroacetone 

Downstream Products

• 108535-33-7 (R)-(+)-1,1,1-trifluoro-2-decanol 
• 111423-27-9 (S)-(-)-(1-trifluoromethyl)nonanol 
• 175840-70-7 (R)-1,1,1-trifluoroheptan-2-ol 
• 130025-35-3 (S)-1,1,1-trifluoroheptan-2-ol 
• 198019-16-8 (S)-1-((S)-1-phenylethylamino)-3,3,3-trifluoro-2-propanol 
• 242802-45-5 (S)-3,3,3-trifluoro-1-phenylseleno-2-propanol 
• 902757-59-9 (S)-1,1,1-Trifluoro-3-[methyl-((E)-3-phenyl-allyl)-amino]-propan-2-ol 
• 374-01-6 (S)-1,1,1-trifluoro-2-propanol 
• 142599-69-7 2-hydroxy-3,3,3-trifluoropropyltriphenylphosphonium trifluoroacetate 
• 330-72-3 (S)-1,1,1-trifluoro-2-hydroxy-3-phenylpropane 
• 132871-34-2 (S)-3-(2,5-Dimethyl-phenyl)-1,1,1-trifluoro-propan-2-ol 

Relevant articles and documents

Method for Industrial Production of Optically Active Fluoroalkyl Ethylene Oxide

It is possible to produce an optically active fluoroalkyl chloromethyl alcohol with a high optical purity and a good yield by treating a fluoroalkyl chloromethyl ketone with a microorganism having an activity for asymmetrically reducing the ketone or an enzyme having the activity. Then, it is possible to obtain a fluoroalkyl ethylene oxide by treating the alcohol with a base. Industrial implementation of the production method of the present invention is easy.

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols

The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by chiral (salen)CoIII complex 1·OAc affords both recovered unreacted epoxide and 1,2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several appealing features from a practical standpoint, including the use of H2O as a reactant and low loadings (0.2-2.0 mol %) of a recyclable, commercially available catalyst. In addition, the HKR displays extraordinary scope, as a wide assortment of sterically and electronically varied epoxides can be resolved to ≥ 99% ee. The corresponding 1,2-diols were produced in good-to-high enantiomeric excess using 0.45 equiv of H2O. Useful and general protocols are provided for the isolation of highly enantioenriched epoxides and diols, as well as for catalyst recovery and recycling. Selectivity factors (krel) were determined for the HKR reactions by measuring the product ee at ca. 20% conversion. In nearly all cases, krel values for the HKR exceed 50, and in several cases are well in excess of 200.