21731-17-9

Basic information

• Product Name: methyl 3-aminocrotonate
• Synonyms: (Z)-3-Amino-2-butenoic acid methyl;(Z)-3-Amino-2-butenoic acid methyl ester;3-Aminocrotonic acid methyl;β-Aminocrotonic acid methyl;Einecs 244-549-6;Methyl (Z)-3-aminocrotonate;Methyl (2Z)-3-amino-2-butenoate
• CAS NO: 21731-17-9
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• EINECS: 244-549-6
• Mol File: 21731-17-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 81-83℃
• Boiling Point: 194.1 °C at 760 mmHg
• Flash Point: 65.3 °C
• Appearance: /
• Density: 1.031 g/cm³
• Vapor Pressure: 0.166mmHg at 25°C
• Refractive Index: 1.439
• PKA: 5.27±0.70(Predicted)
• Water Solubility: insoluble
• CAS DataBase Reference: methyl 3-aminocrotonate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-aminocrotonate(21731-17-9)
• EPA Substance Registry System: methyl 3-aminocrotonate(21731-17-9)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:; R36/37/38:
• Safety Statements: S26:; S37/39:
• Hazardous Substances Data: 21731-17-9(Hazardous Substances Data)

Usage

General Description

Methyl 3-aminocrotonate is a chemical compound with the molecular formula C6H11NO2. It is an ester, meaning it is formed from the reaction between methanol and 3-aminocrotonic acid. methyl 3-aminocrotonate is commonly used in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds due to its versatile reactivity and potential for forming important carbon-carbon and carbon-nitrogen bonds. Methyl 3-aminocrotonate also has applications as a building block in the production of complex organic molecules and as a reagent in chemical reactions. In addition, it can be used in research laboratories as a starting material for the preparation of biologically active compounds. Overall, this chemical compound has significant importance in the field of organic chemistry and drug discovery.

InChI:InChI=1/C5H9NO2/c1-4(6)3-5(7)8-2/h6H,3H2,1-2H3/b6-4+

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 72569-97-2 methyl (Z)-3-acetamido-2-butenoate 
• 100-46-9 benzylamine 
• 631-61-8 ammonium acetate 
• 14205-39-1 methyl 3-aminocrotonate 
• 62-53-3 aniline 

Downstream Products

• 57310-23-3 3a,8a-dihydroxy-2-methyl-8-oxo-3,3a,8,8a-tetrahydro-3-aza-cyclopenta[a]indene-1-carboxylic methyl ester 
• 256530-68-4 4-(1-Benzyl-4-nitro-imidazol-5-yl)-2,6-dimethyl-pyridin-3,5-dicarbonsaeuredimethylester 
• 256530-69-5 4-(1-Benzyl-2-methyl-4-nitro-imidazol-5-yl)-2,6-dimethyl-pyridin-3,5-dicarbonsaeuredimethylester 
• 157066-76-7 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid (N[3-(4,4-diphenylpiperidin-1-yl)propyl]amide methyl ester) 
• 28483-35-4 methyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate 
• 100427-26-7 lercanidipine 
• 91116-19-7 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 3-chloropropyl ester 
• 100427-00-7 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 2-chloroethyl ester 
• 92130-26-2 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester 
• 54527-89-8 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester 

Relevant articles and documents

A mechanistic study of the ammonolysis of alkyl acetoacetates in water. Formation of 1,5-dimethyl-2,6,9-triaza-bicyclo[3.3.1]nonane-3,7-dione as the main product

Ammonolysis of alkyl acetoacetates with 15% NH3 in water at room temperature initially lead to formation of alkyl β-aminocrotonates which slowly converted into 1,5-dimethyl-2,6,9-triaza-bicyclo[3.3.1]nonane-3,7-dione as the main product.

Practical, catalytic enantioselective hydrogenation to synthesize N -unprotected β-amino esters

Practical and simple catalytic enantioselective hydrogenation reactions to synthesize N-unprotected β-amino esters have been developed: (1) asymmetric hydrogenation of N-unprotected β-enamine ester and (2) asymmetric direct reductive amination of β-keto esters using ammonium salts. A Ru-DM-SEGPHOS complex was used as the catalyst in both cases and gave high enantioselectivity, high reactivity, and wide substrate applicability. These protocols greatly reduced reaction time and waste compared to conventional synthetic routes. The direct reductive amination route was demonstrated on a >100 kg scale.

Detection and elimination of product inhibition from the asymmetric catalytic hydrogenation of enamines

(Chemical Equation Presented) The catalytic asymmetric hydrogenation of enamine amides and esters with catalyst Rh-1a, prepared from ferrocenyl based ligand 1a or 1b and [(COD)RhCl]2, has been shown through kinetic studies to suffer from product inhibition. Enamine ester substrates have also been shown to be incompatible with the amine products of the reaction in methanol. In situ protection of the amine products with di-tert-butyl dicarbonate eliminates functional group incompatibility of ester substrates and eliminates product inhibition in the reaction.