1365321-55-6

Basic information

• Product Name: (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol
• Synonyms: (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol
• CAS NO: 1365321-55-6
• Molecular Weight: 206.164
• Mol File: 1365321-55-6.mol

Chemical Properties

• CAS DataBase Reference: (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol(1365321-55-6)
• EPA Substance Registry System: (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol(1365321-55-6)

Safety Data

• Hazardous Substances Data: 1365321-55-6(Hazardous Substances Data)

Upstream product

• 955403-59-5 3-(2,4,5-trifluorophenyl)propanal 
• 17533-08-3 1-iodo-2,4,5-trifluorobenzene 
• 165047-24-5 2,4,5-trifluorobenzaldehyde 

Downstream Products

• 868071-17-4 3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid 
• 1283096-74-1 (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile 
• 1352613-29-6 (S)-ethyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate 

Relevant articles and documents

A novel synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by sharpless asymmetric epoxidation method

Synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by the Sharpless asymmetric epoxidation reaction has been achieved. 2,4,5-Trifluorobenzaldehyde with methyl 2-(triphenyl-λ5-phosphanylidene)acetate gave methyl (E)-3-(2,4,5-trifluorophenyl)acrylate in 83% yield. The reduction of ester group with DibalH followed by Sharpless asymmetric epoxidation gave ((2R,3R)-3-(2,4,5-trifluorophenyl)oxiran-2-yl)methanol. Pd/C-catalyzed hydrogenation of epoxy alcohol furnished (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol with >90% ee and 71% yield.

Novel and stereospecific synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol from D-mannitol

A stereospecific synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol from D-mannitol has been developed. The reaction of 2,3-O-isopropylidene-D-glyceraldehyde with 2,4,5-trifluorophenylmagnesium bromide gave [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](2,4,5-trifluorophenyl)methanol in 65% yield as a mixture of diastereoisomers (1-:-1). The Ph3P catalyzed reaction of the latter with C2Cl6 followed by reduction with Pd/C-catalyzed hydrogenation gave (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol with >99% ee and 65% yield.

Novel and enantioselective syntheses of (R)- and (S)-3-hydroxy-4-(2,4,5- trifluorophenyl)butanoic acid: A synthon for sitagliptin and its derivatives

A new synthetic strategy for (R)- and (S)-3-hydroxy-4-(2,4,5- trifluorophenyl)butanoic acid, a building block in the preparation of sitagliptin and its derivatives, was developed. Pd(OAc)2 catalyzed coupling of 2,4,5-trifluoro-1-iodobenzene wit