193539-61-6

Basic information

• Product Name: 2-cyanoethyl 3-aminobut-2-enoate
• Synonyms: 2-cyanoethyl 3-aminobut-2-enoate;(2Z)-3-Amino-but-2-enoic acid 2-cyanoethyl ester;2-cyanoethyl β-amino-crotonate;cyanoethyl 3-aminocrotonate;cyanoethyl-3-aminocrotonate;β-cyanoethyl β-aminocrotonate;(Z)-3-Amino-but-2-enoicacid2-cyano-ethyl ester
• CAS NO: 193539-61-6
• Molecular Formula: C₇H₁₀N₂O₂
• Molecular Weight: 154.1665
• Mol File: 193539-61-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 345.6±22.0 °C(Predicted)
• Appearance: /
• Density: 1.116±0.06 g/cm3(Predicted)
• Solubility: Dichloromethane; Methanol
• PKA: 5.18±0.70(Predicted)
• CAS DataBase Reference: 2-cyanoethyl 3-aminobut-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyanoethyl 3-aminobut-2-enoate(193539-61-6)
• EPA Substance Registry System: 2-cyanoethyl 3-aminobut-2-enoate(193539-61-6)

Safety Data

• Hazardous Substances Data: 193539-61-6(Hazardous Substances Data)

Usage

Description

2-Cyanoethyl 3-aminobut-2-enoate, also known as 2-cyanoethyl 3-aminocrotonate, is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its cyanoethyl and aminobutenoate functional groups, which contribute to its reactivity and utility in chemical reactions.

Uses

Used in Pharmaceutical Industry:
2-Cyanoethyl 3-aminobut-2-enoate is used as an intermediate in the synthesis of 3-O-Desethyl-5-O-desmethyl Amlodipine (D291305) for [application reason] the development of novel calcium channel blockers.
Used in Synthesis of Amlodipine Impurities:
2-Cyanoethyl 3-aminobut-2-enoate is used as a key compound in the synthesis of 3-O-Desethyl-5-O-desmethyl Amlodipine (D291305), which is an impurity of Amlodipine (A633495). Amlodipine is a well-known dihydropyridine calcium channel blocker used in the treatment of hypertension and angina. The synthesis of this impurity helps in understanding the side products formed during the production process and ensures the purity and safety of the final drug product.

Upstream product

• 65193-87-5 2-cyanoethylacetoacetate 

Downstream Products

• 110962-94-2 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate methyl ester-(2-cyanoethyl)ester 
• 88249-98-3 2,6-Dimethyl-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-methyl ester 
• 75130-29-9 J-6-163 
• 167963-69-1 2-Acetoxymethyl-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-(2-cyano-ethyl) ester 3-ethyl ester 
• 75130-30-2 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-(2-methylsulfanyl-ethyl) ester 
• 167963-68-0 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-acetylsulfanyl-ethyl) ester 5-(2-cyano-ethyl) ester 
• 121591-70-6 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(3-acetoxy-propyl) ester 5-(2-cyano-ethyl) ester 
• 167963-62-4 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-(3-phenylsulfanyl-propyl) ester 
• 167409-41-8 2-cyanoethyl 2-(nicotinoylamino)ethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 104043-56-3 5-(2-cyanoethyl) 3-methyl 4-(3-chloro-6-fluoro-2-(trifluoromethyl)phenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate 
• 228562-11-6 2-cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-[3-(2-oxopyrrolidine-1-yl)propylcarbamoyl]-1,4-dihydropyridine-3-carboxylate 
• 228562-58-1 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate 

Relevant articles and documents

Structure-activity relationship study of 1,4-dihydropyridine derivatives blocking N-type calcium channels

Cilnidipine is a 1,4-dihydropyridine derived L/N-type calcium channel dual blocker possessing neuroprotective and analgesic effects which are related to its N-type calcium channel inhibitory activity. In order to find specific N-type calcium channel blockers with the least effects on cardiovascular system, we performed structure-activity relationship study on APJ2708, which is a derivative of cilnidipine, and found a promising N-type calcium channel blocker 21b possessing analgesic effect in vivo with a 1600-fold lower activity against L-type calcium channels than that of cilnidipine.

Isomers of 1-azabicyclo(2.2.2)oct-3-yl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-nitropyridine-3-carboxylate

The four stereoisomers are disclosed having the formula: STR1 in which the asymmetric centers a and b are the same or different. The compounds are derived from the (+) and (-) alcohols and the (+) and (-) dihydropyridines and have either the absolute R or