74839-83-1

Basic information

• Product Name: (2S,3S)-(-)-2,3-BUTANEDIOL DI-P-TOSYLATE
• Synonyms: (-)-2,3-BUTANEDIOL DI-P-TOSYLATE;(2S,3S)-(-)-2,3-BUTANEDIOL DI-P-TOSYLATE;(2R,3R)-2,3-DI-O-TOSYLBUTANEDIOL;(2S,3S)-(-)-Di-O-tosyl-2,3-butanediol;(-)-2,3-BUTANEDIOL DI(P-TOLUENESULFONATE );(-)-2,3-butanediyl di(p-toluenesulfonate)
• CAS NO: 74839-83-1
• Molecular Formula: C₁₈H₂₂O₆S₂
• Molecular Weight: 398.49
• Mol File: 74839-83-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 67-69 °C(lit.)
• Boiling Point: 550.2°C at 760 mmHg
• Flash Point: 286.5°C
• Appearance: /
• Density: 1.273g/cm³
• Vapor Pressure: 1.37E-11mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: (2S,3S)-(-)-2,3-BUTANEDIOL DI-P-TOSYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-(-)-2,3-BUTANEDIOL DI-P-TOSYLATE(74839-83-1)
• EPA Substance Registry System: (2S,3S)-(-)-2,3-BUTANEDIOL DI-P-TOSYLATE(74839-83-1)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 74839-83-1(Hazardous Substances Data)

Usage

General Description

(2S,3S)-(-)-2,3-butanediol di-p-tosylate is a chemical compound that is commonly used as a reagent in organic synthesis. (2S,3S)-(-)-2,3-BUTANEDIOL DI-P-TOSYLATE is a diol derivative, with two hydroxyl groups and two p-tosylate groups attached to a butanediol backbone. The stereochemistry of the compound is specified by the (2S,3S)-(-)- designation, indicating the configuration of the chiral centers in the molecule. The p-tosylate groups make the compound a good leaving group in substitution reactions, and the diol functionality gives it the ability to participate in various types of reactions, such as oxidation and reduction. (2S,3S)-(-)-2,3-BUTANEDIOL DI-P-TOSYLATE is important in the synthesis of pharmaceuticals and other fine chemicals due to its versatile reactivity and stereochemical properties.

InChI:InChI=1/C18H22O6S2/c1-13-5-9-17(10-6-13)25(19,20)23-15(3)16(4)24-26(21,22)18-11-7-14(2)8-12-18/h5-12,15-16H,1-4H3/t15-,16-/m1/s1

Upstream product

• 135638-22-1 <2R-(2α(2S*,3S*),3aα,4α,7α,7aα)>-3-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-2-butanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 19132-06-0 (2S,3S)-butane-2,3-diol 
• 24347-58-8 (R,R)-2,3-butandiol 
• 6982-25-8 d,l-2,3-butanediol 

Downstream Products

• 1450903-80-6 (2R,3R)-bis(2-iodo-3-nitrophenoxyl)butane 
• 74839-84-2 (R,R)-chiraphos 

Relevant articles and documents

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Highly Active and Selective Ethylene Oligomerization Catalyst and Method of Preparing Hexene or Octene Using the Same

This invention relates to a chromium complex compound for selective ethylene oligomerization including a chiral ligand, and to a method of selectively preparing 1-hexene or 1-octene from ethylene using the same.

SYNTHESIS OF OPTICALLY PURE COMPOUNDS BY ENANTIOTOPICALLY DIFFERENTIATING MONOACETALIZATION OF PROCHIRAL DIKETONES. PART II. FRAGMENTATION OF β-KETO-ACETALS

Treatment of β-keto-acetals, derived from non-enolisable β-diketones, with sulfonic acids in boiling benzene results in a smooth retro-Claisen-type fragmentation.The acetal-C-atom is thereby transformed into a carboxylic ester via a dialkoxycarbenium ion, which is dealkylated by the sulfonate counter-ion.Application of this reaction to the diastereomeric monoacetals 3 and 4, derived from cis-9-methyl-decalin-1,8-dione (1), followed by transesterification with CH3OH, yields optically pure 4-(2'-methyl-3'-oxocyclohexyl)butyrate 9 ((+)-9 from 3, (-)-9 from 4) and the monosulfonate of meso-2,3-butanediol (-)-13 (Scheme 2).Unexpected, this cleavage proceeds as well with monoacetal 26, obtained by acetalization of trans-9-methyl-decalin-1,8-dione (27) with 2,2-dimethyl-1,3-propanediol (Scheme 7).Some attempts, aiming at an isomerization of the cis- and trans-decalin derivatives 3 and 24, or 25 and 26, via the postulated carboxonium intermediate, were not successful.