74653-99-9

Basic information

• Product Name: (S,S)-(+)-1,4-Bis(N-methylanilino)-2,3-butandiol
• CAS NO: 74653-99-9
• Molecular Weight: 300.401
• Mol File: 74653-99-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S,S)-(+)-1,4-Bis(N-methylanilino)-2,3-butandiol(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-(+)-1,4-Bis(N-methylanilino)-2,3-butandiol(74653-99-9)
• EPA Substance Registry System: (S,S)-(+)-1,4-Bis(N-methylanilino)-2,3-butandiol(74653-99-9)

Safety Data

• Hazardous Substances Data: 74653-99-9(Hazardous Substances Data)

Upstream product

• 298-18-0 (S,S)-diepoxybutane 
• 100-61-8 N-methylaniline 
• 62-53-3 aniline 
• 74-88-4 methyl iodide 
• 1464-53-5 rac-1,2,3,4-diepoxybutane 
• 564-00-1 meso-1,2,3,4-diepoxybutane 

Relevant articles and documents

Preparation of Some Chiral Aminodiols from Tartaric Acid. Chiral Lithium Aluminium Hydride Derivatives for Asymmetric Ketone Reductions

The nitrogen- and oxygen-substituted chiral diols 1 are prepared from tartaric or malic acid.For the introduction of the amino groups, tartaric acid derived electrophiles of increasing reactivity are used: The diester (-> 3), the ditosylate 4 (-> 5), the diepoxide 6 ( -> 1a, e, g, h), and the acyl chloride 7a.The alkylating reagents 9a and 10c, obtained from malic acid, are employed for the synthesis of 1i. - The diols 1 react with lithium aluminium hydride to give complexes, for which a cyclic structure 2 is assumed, and which reduce ketones with prochiral carbonyl C-atoms to optically active alcohols (Table 1 and 2).From the effect of substitution and from the sense of chirality of the predominantly formed enantiomers, several models 11 - 16 are discussed as possible mechanisms of this asymmetric synthesis.