56512-51-7

Basic information

• Product Name: vinylglycine
• Synonyms: vinylglycine;(2S)-2-Amino-3-butenoic acid;2-Vinyl-L-glycine
• CAS NO: 56512-51-7
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.1
• Mol File: 56512-51-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 256.1°Cat760mmHg
• Flash Point: 108.7°C
• Appearance: /
• Density: 1.144g/cm³
• PKA: 1.99±0.10(Predicted)
• CAS DataBase Reference: vinylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: vinylglycine(56512-51-7)
• EPA Substance Registry System: vinylglycine(56512-51-7)

Safety Data

• Hazardous Substances Data: 56512-51-7(Hazardous Substances Data)

Usage

General Description

Vinylglycine is a chemical compound with the molecular formula C4H11NO2. It is a derivative of the amino acid glycine and is commonly used in the synthesis of pharmaceuticals and agrochemicals. Vinylglycine is known for its ability to inhibit the biosynthesis of the amino acid methionine, making it a potential tool for the control of methionine-dependent tumors. Additionally, it has been studied for its potential use in the treatment of neurodegenerative diseases. However, vinylglycine is also known to be toxic to certain plants and can have detrimental effects on agricultural crops. Therefore, its use and handling must be carefully regulated to minimize its impacts on the environment.

Upstream product

• 600-17-9 vinyl glycolic acid 
• 100038-68-4 2-tert-Butoxycarbonylamino-but-3-enoic acid methyl ester 
• 104523-58-2 2-benzyl 2-N-tert-butoxycarbonylamino-3-butenoate 
• 133559-28-1 2-(Benzhydrylidene-amino)-but-3-enoic acid methyl ester 
• 70562-47-9 ethyl 2-acetamido-2-(ethoxycarbonyl)but-3-enoate 
• 107-93-7 (E)-but-2-enoic acid 

Downstream Products

• 171077-04-6 (+/-)-2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-butenoic acid 
• 59-51-8 DL-methionine 
• 617-65-2 Glutamic acid 
• 6667-60-3 2-amino-3-methylbutanedioic acid 

Relevant articles and documents

Simple Synthesis of L- and D-Vinylglycine (2-Aminobut-3-enoic Acid) and Related Amino Acid

A three-step synthesis of vinylglycine 1 has been developed using a readily available starting material (but-3-enenitrile 2), based on the Neber rearrangement of the corresponding N-chloroimidate, and using cheap, convenient reagents.Also described is a convenient optical resolution of the N-tert-butoxycarbonyl derivative by papain-catalysed enantioselective esterifucation in a two-phase system.From the optically active amino acid, related amino acids obtained via epoxidation, dihydroxylation and cyclopropanation have been prepared.The related β,γ-unsaturated amino acids (E)-2-aminopent-3-enoic acid 20 and (E)-2-amino-3-methylpent-3-enoic acid 22 have been synthesised using the same approach.

ENANTIOSELECTIVE ELECTROPHILIC BOND CONSTRUCTION TO THE α-CARBON OF α-AMINOACIDS

In this report, we describe three possibilities for aminoacid synthesis using an enantioselective electrophilic process.Thus, enantioselective carboxylation, alkylation and protonation of Schiff bases yield optically active aminoacids with e.e. up to 76percent.