68935-25-1

Basic information

• Product Name: l-nicotine di-(p-toluoyl)-d-tartrate
• Synonyms: l-nicotine di-(p-toluoyl)-d-tartrate
• CAS NO: 68935-25-1
• Molecular Weight: 548.593
• Mol File: 68935-25-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: l-nicotine di-(p-toluoyl)-d-tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: l-nicotine di-(p-toluoyl)-d-tartrate(68935-25-1)
• EPA Substance Registry System: l-nicotine di-(p-toluoyl)-d-tartrate(68935-25-1)

Safety Data

• Hazardous Substances Data: 68935-25-1(Hazardous Substances Data)

Upstream product

• 93-60-7 methyl 3-pyridinecarboxylate 
• 25162-00-9 D-nicotine 
• 32634-68-7 (2S,3S)-di-4-toluoyltartaric acid 
• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 54-11-5 nicotin 

Relevant articles and documents

SYNTHESIS AND RESOLUTION OF NICOTINE

The present disclosure generally relates to methods of preparing nicotine and resolving R,S nicotine to enrich the (S)(?) enantiomer. The method may comprise combining N-methyl-2-pyrrolidone or a salt thereof with a nicotinate compound in the presence of a solvent and a strong base to form 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof; and reducing the 1-methyl-3-nicotinoyl-2-pyrrolidone or salt thereof in solution with Na2S2O4 to produce racemic nicotine or salt thereof. Resolving the racemic nicotine (or other enantiomeric mixture) may comprise combining the nicotine with (?)-O,O′-di-p-toluoyl-L-tartaric acid (L-PTTA).

A process for the resolution of (R,S)-nicotine

(R,S)-Nicotine was resolved through diastereomeric salt formation using dibenzoyl-d-tartaric acid and dibenzoyl-l-tartaric acid to obtain enantiomerically pure (S)-nicotine and (R)-nicotine.