(2S)-2-(trifluoromethyl)oxirane

Base Information

• Chemical Name: (2S)-2-(trifluoromethyl)oxirane
• CAS No.: 130025-34-2
• Molecular Formula: C3H3 F3 O
• Molecular Weight: 112.051
• Hs Code.: 2910900090
• DSSTox Substance ID: DTXSID001304532
• Nikkaji Number: J476.724A
• Mol file: 130025-34-2.mol

Synonyms:130025-34-2;(2S)-2-(trifluoromethyl)oxirane;(S)-2-(trifluoromethyl)oxirane;(S)-(-)-3,3,3-Trifluoro-1,2-epoxypropane;Oxirane, 2-(trifluoromethyl)-, (2S)-;(S)-3,3,3-Trifluoro-1,2-Epoxypropane;MFCD04128982;(S)-2-Trifluoromethyl-oxirane;(S)-(-)-2-Trifluoromethyloxirane;Oxirane, (trifluoromethyl)-, (2S)-;(S)-2-trifluoromethyloxirane;SCHEMBL690652;(S)-2-(trifluoromethyl) oxirane;DTXSID001304532;(S)-2alpha-(Trifluoromethyl)oxirane;(S)-(-)-2-(Trifluoromethyl)oxirane;AKOS015991426;AKOS016016392;FF-0746;(s)-(-)-3,3,3-trifluoropropene oxide;BP-12580;(2S)-2-(trifluoromethyl)oxirane >98%ee;EN300-222102;N12669;(2S)-(-)-3,3,3-Trifluoro-1,2-propenoxide;(S)-(-)-3,3,3-Trifluoro-1,2-epoxypropane, 97%

Chemical Property of (2S)-2-(trifluoromethyl)oxirane

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 560mmHg at 25°C
• Melting Point: -80
• Refractive Index: n20/D <1.300
• Boiling Point: 40
• Flash Point: 80.4°C
• PSA: 12.53000
• Density: 1.074g/cm³
• LogP: 0.94750
• Storage Temp.: ?20°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 112.01359920
• Heavy Atom Count: 7
• Complexity: 76.7

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-2-(trifluoromethyl)oxirane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F,F+
• Statements: 12
• Safety Statements: 3

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)C(F)(F)F
• Isomeric SMILES: C1[C@H](O1)C(F)(F)F
• Uses: Precursor to a trifluoromethyl chiral auxiliary which promotes a highly diastereoselective Simmons-Smith cyclopropanation.

Technology Process of (2S)-2-(trifluoromethyl)oxirane

There total 5 articles about (2S)-2-(trifluoromethyl)oxirane 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: 82.0%

3-bromo-1,1,1-trifluoropropan-2-ol (137429-44-8) → (S)-2-trifluoromethyl-oxirane (130025-34-2) + (2R)-2-(trifluoromethyl)oxirane (143142-90-9)

Guidance literature:

With sodium hydroxide; at 95 - 100 ℃; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00106a012

Reference yield: 42.0%

1,1,1-trifluoro-2,3-epoxypropane (359-41-1) → (S)-2-trifluoromethyl-oxirane (130025-34-2) + (S)-(-)-1,2-Dihydroxy-3,3,3-trifluoropropane (148683-14-1) + (2R)-2-(trifluoromethyl)oxirane (143142-90-9)

Guidance literature:

With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water; at 0 - 20 ℃;

DOI:10.1021/ja016737l

Reference yield: 37.0%

1,1,1-trifluoro-2,3-epoxypropane (359-41-1) → poly((R)-1,1,1-trifluoro-2,3-epoxypropane) + (S)-2-trifluoromethyl-oxirane (130025-34-2) + (2R)-2-(trifluoromethyl)oxirane (143142-90-9)

Guidance literature:

C₆₄H₇₄Cl₂Co₂N₄O₄; bis(triphenylphosphoranylidene)-ammonium acetate; In toluene; at 0 ℃; for 0.0333333h; Product distribution / selectivity;

upstream raw materials:

3-bromo-1,1,1-trifluoroacetone

3-bromo-1,1,1-trifluoropropan-2-ol

1,1,1-trifluoro-2,3-epoxypropane

Downstream raw materials:

(S)-1,1,1-trifluoro-3-[2-(3-methoxyphenyl)-1,1-dioxo-1λ⁶-thiomorpholin-4-yl]-propan-2-ol

Refernces

• 1、 -. "ISOSELECTIVE POLYMERIZATION OF EPOXIDES". Page/Page column 69; 77-78. . Retrieved 2009/04/25.
• 2、 Ramachandran, P. Veeraraghavan,Gong, Baoqing,Brown, Herbert C.. "Chiral Synthesis via Organoboranes. 40. Selective Reductions. 55. A Simple One-Pot Synthesis of the Enantiomers of (Trifluoromethyl)oxirane. A General Synthesis in High Optical Purities of α-Trifluoromethyl Secondary Alcohols via the Ring-Cleavage Reactions of the Epoxide". . p. 41 - 46. Retrieved 2007/10/02.