63163-09-7

Basic information

• Product Name: butanedioic acid, 2-butyl-, (2S)-
• Synonyms: (2S)-2-Butylsuccinic acid
• CAS NO: 63163-09-7
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.1944
• Mol File: 63163-09-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 281.299°C at 760 mmHg
• Flash Point: 138.166°C
• Density: 1.16g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: butanedioic acid, 2-butyl-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: butanedioic acid, 2-butyl-, (2S)-(63163-09-7)
• EPA Substance Registry System: butanedioic acid, 2-butyl-, (2S)-(63163-09-7)

Safety Data

• Hazardous Substances Data: 63163-09-7(Hazardous Substances Data)

Upstream product

• 132631-27-7 (E)-butylidenesuccinic acid 
• 10479-26-2 1,2-Biphenylhexane 
• 1039497-34-1 (S)-(+)-3-(nitromethyl)heptanoic acid 

Downstream Products

• 129339-84-0 (R)-2-Butyl-N¹,N⁴-diphenyl-succinamide 
• 129339-92-0 (S)-2-Butyl-N¹,N⁴-diphenyl-succinamide 

Relevant articles and documents

A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin

Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main compounds of interest involved are given, together with their CD spectra.

Enantioselective carbometalation of cinnamyl derivatives: New access to chiral disubstituted cyclopropanes - Configurational stability of benzylic organozinc halides

A stoichiometric or catalytic amount of (-)-sparteine can serve asa promoter for the enantioselective carbolithiation of cinnamyl derivatives by primary and secondary organolithium compounds. The enantiofacial choice of the addition reaction is dependent on the stereochemistry of the initial double bond. The resulting benzylic organolithium compounds can be derivatized to a linear phenylated chain that bears two contiguous stereogenic centers with given configurations. The use of the dimethyl acetal of the (E)-cinnamyl alcohol allows the highest enantioselective carbolithiation and by simply warming the reaction mixture to room temperature, the resulting benzylic organo-lithium intermediate undergoes a 1,3-elimination to give the chiral disubstituted cyclopropane in high enantiomeric excess (90-95% ee). Another significant finding is the observation that the Li-Zn transmetalation in a benzylic species occurs with inversion of configuration, and the corresponding acyclic benzylic zinc halides have observable configurational stability at - 30°C.