4606-55-7

Basic information

• Product Name: dimethyl (2E)-2-piperidin-1-ylbut-2-enedioate
• CAS NO: 4606-55-7
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.257
• Mol File: 4606-55-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 330°C at 760 mmHg
• Flash Point: 153.4°C
• Density: 1.147g/cm³
• Vapor Pressure: 0.000171mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: dimethyl (2E)-2-piperidin-1-ylbut-2-enedioate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl (2E)-2-piperidin-1-ylbut-2-enedioate(4606-55-7)
• EPA Substance Registry System: dimethyl (2E)-2-piperidin-1-ylbut-2-enedioate(4606-55-7)

Safety Data

• Hazardous Substances Data: 4606-55-7(Hazardous Substances Data)

Upstream product

• 16574-34-8 1-(naphthalen-2-ylmethyl)piperidine 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 74-11-3 para-chlorobenzoic acid 
• 2905-56-8 N-Benzylpiperidine 

Relevant articles and documents

Dimethylbut-2-ynedioate mediated esterification of acids via sp3 C-N bond cleavage of benzylic tertiary amines

A straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acids was demonstrated in this manuscript. The present protocol can be regarded as a straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acid. Moreover, the reaction is fundamentally new chemistry for the sp 3 C-N bond cleavage coupled with esterification. The esterification reaction conditions are very mild and functional group-tolerated, such as hydrosilanes, alcohols, phenol, and amino acids. A mechanism is proposed in which the tertiary amine reacts with dimethyl but-2-ynedioate to form zwitterionic salt, and then the zwitterionic intermediate subsequently accept hydrogen to assist the nucleophilic attack of oxygen atom of carboxyl group at the benzyl group of tertiary amine, while a separate reaction pathway leads to esterification.