13412-12-9

Basic information

• Product Name: METHYL 3-METHYLAMINOCROTONATE
• Synonyms: METHYL 3-(METHYLAMINO)BUT-2-ENOATE;METHYL 3-METHYLAMINOCROTONATE;Methyl 3-methylaminocrotonate,97%;2-Butenoic acid, 3-(MethylaMino)-, Methyl ester;3-Methylaminobut-2-enoic acid methyl ester;Methyl beta-(methylamino)crotonate;Methyl 3-(methylamino)-2-butenoate;beta-N-methylaminocapronic acid methyl ester
• CAS NO: 13412-12-9
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• Mol File: 13412-12-9.mol
• Article Data: 22

Chemical Properties

• Melting Point: 62-68 °C
• Boiling Point: 187.5°Cat760mmHg
• Flash Point: 67.2°C
• Appearance: /
• Density: 0.969g/cm³
• Vapor Pressure: 1.57mmHg at 25°C
• Refractive Index: 1.431
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 5.73±0.70(Predicted)
• Water Solubility: Soluble in water at (54 g/L) (25°C), Calc.
• CAS DataBase Reference: METHYL 3-METHYLAMINOCROTONATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-METHYLAMINOCROTONATE(13412-12-9)
• EPA Substance Registry System: METHYL 3-METHYLAMINOCROTONATE(13412-12-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 13412-12-9(Hazardous Substances Data)

Usage

Description

METHYL 3-METHYLAMINOCROTONATE is a white crystalline powder that serves as an intermediate in the synthesis of an analogue to amlodipine, which is a medication used to treat hypertension and coronary artery disease. Its chemical structure allows it to be a versatile component in the development of pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
METHYL 3-METHYLAMINOCROTONATE is used as a chemical intermediate for the synthesis of amlodipine analogues, specifically those bearing a short amino polyethylene glycol chain. This application is crucial for the development of new medications with potential improved properties, such as enhanced solubility, stability, or bioavailability, which can contribute to more effective treatments for various cardiovascular conditions.

InChI:InChI=1/C6H11NO2/c1-5(7-2)4-6(8)9-3/h4H2,1-3H3/b7-5+

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 74-89-5 methylamine 
• 17041-60-0 dimethyl ethylidenemalonate 
• 622-29-7 N-Benzylidenemethylamine 
• 624-90-8 methyl azide 
• 623-43-8 methyl crotonate 
• 41607-86-7 β-Azidoisovaleriansaeuremethylester 
• 4091-39-8 3-chloro-2-butanone 

Downstream Products

• 68870-58-6 methyl 3-(p-chlorophenyl)-5-methylisoxazole-4-carboxylate 
• 1423699-80-2 C₁₃H₁₄BrNO₃ 
• 1423700-51-9 C₁₈H₂₅BrN₂O₃Si 
• 1423700-49-5 methyl 3-(4-bromophenyl)-5-methyl-1H-pyrazole-4-carboxylate 
• 90145-26-9 1,5-dimethyl-3-phenyl-1H-pyrazole-4-carboxylic acid methylester 
• 1393485-92-1 methyl 3-(4-fluorophenyl)-1,5-dimethyl-1H-pyrazole-4-carboxylate 
• 1361018-99-6 methyl 5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-carboxylate 
• 1228689-61-9 methyl 5-(4-bromophenyl)-3-methylisoxazole-4-carboxylate 
• 1380650-67-8 isopropyl 1-(4'-(2-(methoxycarbonyl)-3-(methylamino)but-2-enoyl)biphenyl-4-yl)cyclopropanecarboxylate 
• 1228690-12-7 2-(4-Bromo-3-methyl-benzoyl)-3-[(E)-methylimino]-butyric acid methyl ester 
• 85963-90-2 methyl 2-(4-bromobenzoyl)-3-oxo-butanoate 
• 1229193-57-0 2-(4-bromo-benzoyl)-3-[(E)-methylimino]-butyric acid methyl ester 
• 109346-07-8 3-Aza-1,5-dicarbomethoxy-9-(2-chlorophenyl)-3-methyl-2,4-dimethylenebicyclo<3.3.1>nonane 
• 117648-93-8 4-(3,4-Dimethoxy-phenyl)-5-(hydroxyimino-methyl)-1,2-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester 

Relevant articles and documents

New Route to Functionalized Cyclohexenes in Solvent-free Conditions from Enamino Ketones and β-Oxo Alkenes

Enamino ketones 5 react with β-oxo alkenes 4, without solvent, at room temperature or under focused microwaves to give new, highly functionalized cyclohexenes 7 and 9 in good yields. A mechanism is proposed. The procedure is mild, efficient, economical and environmentally benign. - Keywords: solvent-free reactions; enamino ketones; cyclohexenes; β-oxo alkenes

Synthesis of Spiro-Δ2-Pyrrolin-4-One Pseudo Enantiomers via an Organocatalyzed Sulfa-Michael/Aldol Domino Sequence

Δ2-Pyrrolin-4-ones undergo organocatalyzed sulfa-Michael/aldol domino spirocyclizations with mercaptoacetaldehyde dimer. The products contain three contiguous stereocenters (ee up to 99%, dr up to 95:5, 25 examples) and can be transformed into analogues of natural products. With the use of a single catalyst, the absolute configuration of the products were determined by the configuration of the exocyclic double bond of the starting material. These results point at the possibility of a widespread use of unsaturated Δ2-pyrrolin-4-ones in various (organo)catalyzed (cascade) transformations for accessing libraries of 3D-rich pyrrolone-based (spiro)heterocycles. (Figure presented.).

Isoquinolin-1(2H)-ones and 1,6-naphthyridin-5(6H)-ones by an N-acylation-SNAr sequence

A new synthesis of 2,3-dialkyl-4-carbomethoxyisoquinolin-1(2H)-ones and 6,7-dialkyl-8-carbomethoxy-1,6-naphthyridin-5(6H)-ones is reported. The process involves treatment of a β-enaminoester with 2-fluoro-5-nitrobenzoyl chloride, 2-fluorobenzoyl chloride or 2-chloronicotinoyl chloride followed by heating in the presence of base. The conversion, which proceeds by an N-acylation-SNAr reaction sequence, affords 50-86% yields when R 1 is n-alkyl but ≤30% yields when R1 is α-branched.

LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.