14659-03-1

Basic information

• Product Name: 1-Azulenecarboxylic acid methyl ester
• Synonyms: 1-Azulenecarboxylic acid methyl ester
• CAS NO: 14659-03-1
• Molecular Formula: C₁₂H₁₀O₂
• Molecular Weight: 186.21
• Mol File: 14659-03-1.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Azulenecarboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azulenecarboxylic acid methyl ester(14659-03-1)
• EPA Substance Registry System: 1-Azulenecarboxylic acid methyl ester(14659-03-1)

Safety Data

• Hazardous Substances Data: 14659-03-1(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 26452-96-0 methyl indane-1-carboxylate 
• 7206-57-7 1-acetylazulene 
• 50603-71-9 3-methoxycarbonyl-2H-cyclohepta[b]furan-2-one 
• 75-07-0 acetaldehyde 
• 109-92-2 ethyl vinyl ether 
• 67-56-1 methanol 
• 7206-55-5 1-cyanoazulene 
• 124-38-9 carbon dioxide 
• 275-51-4 azulene 
• 120-72-9 indole 
• 128990-79-4 1-formylazulene-3-carboxylic acid methyl ester 
• 855269-41-9 3-hydroxy-decahydro-azulene-1-carboxylic acid methyl ester 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 1201-25-8 azulene-1-carboxylic acid 
• 133592-45-7 bis(3-methoxycarbonyl-1-azulenyl)phenylmethane 
• 275-51-4 azulene 
• 180129-02-6 1-fluoro-3-methylazulene 
• 67949-59-1 1-fluoroazulene 
• 133751-03-8 (3-methoxycarbonyl-1-azulenyl)diphenylmethane 

Relevant articles and documents

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A colourful azulene-based protecting group for carboxylic acids

An intensely blue-coloured protecting group for carboxylic acids has been developed. The protecting group is introduced through a Steglich esterification that couples 6-(2-hydroxyethyl)azulene (AzulE) and the carboxylic acid substrate. Deprotection is effected under basic conditions by the addition of the amidine base DBU, whereupon cleavage occurs, accompanied by a colour change. A two-step deprotection methodology comprising activation with oxalyl chloride and deprotection with a very mild base was developed for use with base-sensitive substrates. The AzulE esters were found to be compatible with other commonly employed protecting groups – silyl ethers, MOM acetals – by studying their orthogonal and concomitant deprotections. The stability of the new protecting group towards various synthetic processes – oxidation, reduction, cross-coupling, olefination and treatment with base – provided the basis of a versatility profile. This indicated that AzulE esters are sensitive to strongly oxidising and basic agents while being compatible with reducing conditions and selected other reactions. The convenience of a highly coloured protecting group for tracking material (and avoiding loss of compound) through laboratory processes warrants further investigation of this and/or related species.

Synthesis and two-electron redox behavior of diazuleno [2,1-a:1,2-c] naphthalenes

The Diels-Alder reaction of di-2-azulenylacetylene with tetraphenylcyclopentadienone afforded 7,8,9,10-tetraphenyldiazuleno[2,1-a:1,2-c]naphthalene in one pot via autoxidation of the presumed 1,2-di-2-azulenylbenzene derivative. In contrast, a similar rea