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

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

Uses

Used in Pharmaceutical Synthesis:
Methyl 3-aminocrotonate is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form important carbon-carbon and carbon-nitrogen bonds, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Production:
In the agrochemical industry, methyl 3-aminocrotonate is utilized as a building block for the creation of complex organic molecules that can be used in the formulation of pesticides, herbicides, and other agricultural chemicals, enhancing crop protection and yield.
Used in Organic Chemistry Research:
Methyl 3-aminocrotonate serves as a reagent in chemical reactions, facilitating the synthesis of new organic compounds and aiding in the exploration of novel chemical pathways and mechanisms in research laboratories.
Used in Drug Discovery:
As a starting material in research, methyl 3-aminocrotonate is instrumental in the preparation of biologically active compounds, playing a crucial role in the discovery and development of potential new drugs and therapeutic agents.

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 
• 62-53-3 aniline 
• 100-46-9 benzylamine 
• 14205-39-1 methyl 3-aminocrotonate 
• 631-61-8 ammonium acetate 

Downstream Products

• 77978-73-5 4-Methoxycarbonyl-5-methyl-2-oxo-4-pyrrolin-3-essigsaeure 
• 95155-00-3 3-[3,5-Dioxo-1-phenyl-pyrazolidin-(4Z)-ylidene]-butyric acid methyl ester 
• 140171-50-2 phthaloyl amlodipine 
• 140171-51-3 4-(2-Chloro-phenyl)-2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-6-methyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-tert-butyl 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 
• 75130-24-4 2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester 
• 119774-22-0 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-[(E)-4-(4-benzhydryl-piperazin-1-yl)-but-2-enyl] ester 5-methyl ester 
• 116308-56-6 AE₀₀₄₇ 
• 21881-77-6 m-nifedipine 
• 76258-19-0 2-(N-formyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 78168-76-0 N-((Z)-2-Methoxycarbonyl-1-methyl-vinyl)-phthalamic acid methyl ester 
• 78168-80-6 N-((E)-2-Methoxycarbonyl-1-methyl-vinyl)-phthalamic acid methyl ester 
• 17438-14-1 2,6-dimethyl-3,5-dimethoxycarbonyl-1,4-dihydropyridine 
• 137481-69-7 1,4-Dihydro-2,6-dimethyl-3,5-dinitro-4-<2-(trifluormethyl)phenyl>-pyridin 

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.

Enantioselective hydrogenation of β-dehydroamino acids on a cinchonidine-modified palladium catalyst

Enantioselective hydrogenation of (Z)-β-dehydroamino acids on a cinchonidine-modified Pd/Al2O3 catalyst was explored. Comparative studies by using (Z)-β-dehydroamino acids and esters identified that the carboxylic group in dehydroamino acids was essentially important to get enantioselectivities (33% for aryl substituted and 46% for alkyl substituted β-dehydroamino acids). This result extended the range of enantioselective hydrogenation of α,β-unsaturated carboxylic acids on chirally modified Pd catalysts and offered a new approach to synthesize optically active β-amino acids.

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.

First straightforward synthesis of 2,4-disubstituted benz[g]isoquinoline-3,5,10(2H)-triones, 1,2,3,5-substituted naphtho[3,2,1-de]isoquinoline-4,7-diones, and 6-substituted benzo[h]pyrido[3,4,5-kl]-1,2,3,4-tetrahydroacridine-5,8-diones

Structural modifications to the benz[g]isoquinoline skeleton of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones were envisaged in order to make future SAR studies possible for this type of bioactive compounds. Several N-substituted benz[g]isoquinoline-3,5,10(2H)-triones were converted to novel 2,4-substituted benz[g]isoquinoline-3,5,10(2H)-triones, new tetracyclic 1,2,3,5-substituted naphtho[3,2,1-de]isoquinoline-4,7-diones, and 6-substituted benzo[h]pyrido[3,4,5-kl]-1,2,3,4-tetrahydroacridine-5,8-diones. All the synthesized target compounds represent new heterocyclic systems, which were previously undescribed in the literature.

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.

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.

An efficient synthesis of 3-substituted 3H-pyrimidin-4-ones

(Equation presented) A novel and practical synthesis of 3-substituted 3H-pyrimidin-4-ones is described. The key step involves the cyclization of enamide esters, derived from readily available β-keto esters, with trimethylaluminum and various primary amines.

BENTONITE K10 CLAY, AN EFFICIENT CATALYST FOR THE FORMATION OF NITROGEN DERIVATIVES

Bentonite K10 clay has been used to catalyze the formation of enamino carbonyl derivatives, 2-methyl-1H-benzimidazoles, Hantzsch 1,4-dihydropyridines, Hantzsch pyridines, 2-substituted 1,3-diphenylimidazolidines, and tetrahydropyranylbenzazoles.

Long-acting dihydropyridine calcium antagonists. 9. Structure activity relationships around amlodipine

The preparation of a range of 1,4-dihydropyridine analogues of amlodipine has been undertaken and their calcium antagonist activities on rat aorta have been evaluated.Increasing the size of the C5 ester group dramatically reduces calcium antagonist activity, a trend which would be compatible with the carbonyl group of that ester binding to the DHP receptor.Amlodipine analogues with extended C3 ester substituents also have lower potency than amlodipine, possibly because of disruption of a favourable interaction between the protonated amino group on the 2-substituentand the DHP receptor.Replacement of the 6-methyl substituent in amlodipine by alkoxyalkyl groups or electron-withdrawing groups is also detrimental to calcium antagonist activity. amlodipine / 1,4-dihydropyridine / structure activity relationship