Applications of Methyl 3-aminocrotonate

Methyl 3-aminocrotonate is a yellowish semi-solid with Molecular Formula: C5H9NO2 and Molecular Weight: 115.13. It is stable at room temperature in closed containers under normal storage and handling conditions. Keep container closed when not in use it. Store Methyl 3-aminocrotonate in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed. The CAS Registry Number is 14205-39-1.

Methyl 3-aminocrotonate is a member of short and unsaturated cahin carboxylic acids; trans-2-butenoic acid in IUPAC sysytem name and 3-methylacrylic acid in acrylic acid series naming. It is a white to off-white crystals; soluble in water (the solution is a weak acid); melting at 71 C; boiling at 185 C. Methyl 3-aminocrotonate reacts violently with bases, oxidants, reducing agents. 

It is found in croton oil used as a standard irritant in pharmacological research; laxative and poisonous to human. Tiglic acid is structurally the trans- form of methyl branched Methyl 3-aminocrotonate found in croton oil (trans-2,3-Dimethylacrylic acid in acrylic acid series naming). The cis- form of methyl branched crotonic acid is called angelic acid obtainable naturally from roots of Angelica plant. 

They are onoclinic poisonous crystals; soluble in hot water. They have a reactive double bond and carboxylic group in one molecule. They can be used as co-monomers for polymerization to prepare functional polymers as well as in protein sequencing and enzyme inhibiting. 

Methyl 3-aminocrotonate is used as intermediate for the syntheses of pharmaceuticals (e.g. 1,4-dihydropyridine derivatives) as well as for the manufacture of stabilizers and plastics.

Methyl 3-aminocrotonate derivatives, acyl halides, anhydrides, esters, amides and nitriles, are used in making target products such as flavoring agents, internal plasticizers, pesticides, dyes, textile treatment agents, fungicides, and pharmaceuticals through further reactions of substitution, catalytic reduction, metal hydride reduction, diborane reduction, keto formation with organometallic reagents, electrophile bonding at oxygen, and Claisen condensation on carboxylic group and electrophilic additions, reduction, oxidation, radical additions, substitution and dienes formation on double bond. Methyl 3-aminocrotonate is used in manufacturing Nitrendipine (chemically, Ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate), a drug to treat mild hypertension.

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