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

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

Downstream Products

• 60-80-0 antipyrine 
• 27525-74-2 dimethyl 2,6-dimethylpyridine-3,5-dicarboxylate 
• 314034-06-5 3-benzyl 5-methyl 2-(2-chloroethoxy)methyl-4-(3-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 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) 

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.

PROCESS FOR PRODUCING AMINO ACID DERIVATIVES

The present invention relates to a process for producing amino acid derivatives such as optically active β-amino acid in short steps with good yield and high optical purity, which comprises reacting a keto acid of the formula (1): wherein R1 is hydrogen, an optionally substituted hydrocarbon, etc.; R2 is a spacer; and R3 is an optionally substituted alkoxy, etc., or a salt thereof, with ammonia or an amine or a salt thereof in the presence of a chiral catalyst and in the presence or absence of an acid and/or a fluorine-containing alcohol, to give an amino acid derivative of the formula (2): wherein Q is a group formed by removing one hydrogen atom from ammonia or an amine; X' is an acid and/or a fluorine-containing alcohol; and b is 0 or 1.