133095-74-6

Basic information

• Product Name: (S)-1-TOSYLOXY-3-BUTEN-1-OL
• Synonyms: (S)-3-BUTENE-1,2-DIOL 1-TOSYLATE;(S)-2-HYDROXY-3-BUTEN-1-YL P-TOSYLATE;(S)-2-HYDROXY-3-BUTEN-1-YL TOSYLATE;(S)-2-HYDROXY-3-BUTENYL-1-TOSYLATE;(S)-2-HYDROXY-3-BUTENYL TOSYLATE;(S)-1-TOSYLOXY-3-BUTEN-1-OL;(S)-3-Butene-1,2-diol-1-(p-toluenesulfonate);(S)-2-HYDROXY-3-BUTEN-1-YL P-TOSYLATE, 99%(GC)
• CAS NO: 133095-74-6
• Molecular Formula: C₁₁H₁₄O₄S
• Molecular Weight: 242.29
• Product Categories: chiral
• Mol File: 133095-74-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 58-63 °C
• Boiling Point: 355.12°C (rough estimate)
• Flash Point: 194.7 °C
• Appearance: White to beige/Crystalline Powder or Crystals
• Density: 1.3329 (rough estimate)
• Vapor Pressure: 4.65E-07mmHg at 25°C
• Refractive Index: 1.5220 (estimate)
• Storage Temp.: 2-8°C
• PKA: 13.01±0.20(Predicted)
• BRN: 4254384
• CAS DataBase Reference: (S)-1-TOSYLOXY-3-BUTEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-TOSYLOXY-3-BUTEN-1-OL(133095-74-6)
• EPA Substance Registry System: (S)-1-TOSYLOXY-3-BUTEN-1-OL(133095-74-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 1-10
• Hazardous Substances Data: 133095-74-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C11H14O4S/c1-3-10(12)8-15-16(13,14)11-6-4-9(2)5-7-11/h3-7,10,12H,1,8H2,2H3/t10-/m0/s1

Upstream product

• 138332-13-5 2-hydroxy-3-butenyl-4-methyl-1-benzenesulfonate 
• 108-05-4 vinyl acetate 
• 98-59-9 p-toluenesulfonyl chloride 
• 138249-06-6 (±)-2-acetoxybut-3-enyl tosylate 
• 62214-39-5 (2S)-but-3-ene-1,2-diol 
• 497-06-3 3,4-butenediol 

Downstream Products

• 138332-14-6 (S)-1-tosyloxy-2-acetyloxy-3-butene 
• 62249-80-3 (S)-(+)-3,4-epoxy-1-butene 
• 913824-96-1 (2R)-2-({2'.6'-dichloro-3-[(1E)-prop-1-enyl]-1,1'-biphenyl-2-yl}oxy)but-3-enyl 4-methylbenzenesulfonate 
• 1200113-25-2 (S,E)-2-hydroxy-5-phenylpent-3-enyl 4-methylbenzenesulfonate 
• 1200113-24-1 (S,E)-2-hydroxyoct-3-enyl 4-methylbenzenesulfonate 
• 615251-46-2 toluene-4-sulfonic acid (S)-2-cyclopropyl-2-hydroxy-ethyl ester 
• 1426685-40-6 C₂₇H₃₂O₄SSi 
• 1047665-66-6 C₁₈H₁₈BrNO₄S 
• 1047664-13-0 C₁₉H₁₉BrO₄S 
• 510766-92-4 (2R)-2H-chromen-2-ylmethyl 4-methylbenzenesulfonate 

Relevant articles and documents

Synthesis of enantiomerically pure 3-butene-1,2-diol derivatives via a Sharpless asymmetric epoxidation route

A short enantiospecific synthesis of the butenediol monotosylates (1,2), the epoxybutanediol monotosylates (3,4) and the epoxybutenes (5,6) is described.

Synthesis of the C1-C15 fragment of elaiolide

The synthesis of the C1-C15 fragment of elaiolide was achieved by successfully utilizing the desymmetrization strategy, zirconium catalyzed C-C bond formation and double stereodifferentiating aldol reactions. The Royal Society of Chemistry.

Three step synthesis of single diastereoisomers of the vicinal trifluoro motif

A three step route to single diastereoisomers of the vicinal trifluoromethyl motif is described. The route starts from either syn- or anti-α,β-epoxy alcohols and takes a direct approach in that each of the three steps introduces a fluorine atom in a regio- and stereospecific manner. Starting from either the syn- or the anti-α,β-epoxy alcohol, stereospecific reactions generate two separate diastereoisomeric series of this motif. The route is a significant improvement on an earlier six step strategy.