54380-72-2

Basic information

• Product Name: 5-Azulenecarboxylic acid methyl ester
• Synonyms: 5-Azulenecarboxylic acid methyl ester
• CAS NO: 54380-72-2
• Molecular Formula: C12H10O2
• Molecular Weight: 186.21
• Mol File: 54380-72-2.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Azulenecarboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Azulenecarboxylic acid methyl ester(54380-72-2)
• EPA Substance Registry System: 5-Azulenecarboxylic acid methyl ester(54380-72-2)

Safety Data

• Hazardous Substances Data: 54380-72-2(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 1202-03-5 azulene-5-carboxylic acid 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 132346-39-5 (+/-)-(1ar)-1a,2,4,5,6,6b-hexahydro-1H-2c,6ac-ethano-cycloprop[e]indene-1ξ,7anti,8anti-tricarboxylic acid-7,8-anhydride-1-methyl ester 
• 1208-33-9 ethyl azulene-5-carboxylate 

Relevant articles and documents

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A Thermolytic Azulene Synthesis from Dimethyl 4-Morpholino-3,3a,8,8a-tetrahydroazulene-5,6-dicarboxylates and Its 1-Substituted Derivatives

The thermolysis of 1-substituted 4-morpholino-3,3a,8,8a-tetrahydroazulene-5,6-dicarboxylates derivatives (7a-c) under catalytic dehydrogenation conditions was studied. The reaction substrates were prepared by a several-step sequence involving the [2+2] cycloaddition of bicycle morpholino enamines with dimethyl acetylenedicarboxylate, and a subsequent electrocyclic opening of the cyclobutene ring as a key skeletal construction, starting from bicyclo[3.3.0]octane-2,6-dione mono(ethylene acetal). Refluxing of a diphenyl ether solution of dimethyl 4-morpholino-3,3a,8,8a-tetrahydroazulene-5,6dicarboxylate (7a) containing a catalytic amount of Pd-C gave a 10% yield of dimethyl azulene-5,6-dicarboxylate (8a), accompanied by a 10% yield of dimethyl azulene-4,6-dicarboxylate (9a), trace amounts of dimethyl azulene-5,7-dicarboxylate (10a), methyl azulene-5-carboxylate (12a), and methyl azulene-6-carboxylate (13a). Under the same thermolytic conditions, a 1-phenyl-substituted compound 7b gave corresponding similar types of phenyl-substituted azulenes (8b, 9b, 10b, 11b, and 14b), and a 1-cyano-substituted compound 7c gave a mixture of corresponding similar types of cyano-substituted azulenes (8c, 9c, 10c, and 11e). This sequence provides a new method for synthesizing substituted azulenes suffering from migration and removal of one ester group. Also the thermolysis of a similar system of dimethyl 3-(l-pyrrolidinyl)-2,7-cycloheptadiene-l,2-dicarboxylate (15), even in the absence of a catalyst, gave cycloheptatriene derivatives of dimethyl 1,3,5-cycloheptatriene-dicarboxylate (16, 17, 18, and 19), bearing no morpholine molecule.