54654-48-7

Basic information

• Product Name: METHYL-2-METHYLAZULENE-1-CARBOXYLATE
• Synonyms: METHYL-2-METHYLAZULENE-1-CARBOXYLATE
• CAS NO: 54654-48-7
• Molecular Formula: C₁₃H₁₂O₂
• Molecular Weight: 200.23318
• Mol File: 54654-48-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL-2-METHYLAZULENE-1-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-2-METHYLAZULENE-1-CARBOXYLATE(54654-48-7)
• EPA Substance Registry System: METHYL-2-METHYLAZULENE-1-CARBOXYLATE(54654-48-7)

Safety Data

• Hazardous Substances Data: 54654-48-7(Hazardous Substances Data)

Usage

General Description

Methyl-2-methylazulene-1-carboxylate is a chemical compound that belongs to the azulene family, which is known for its blue color and aromatic properties. METHYL-2-METHYLAZULENE-1-CARBOXYLATE is derived from azulene and contains a methyl group and a carboxylic acid group. It is commonly used in the fragrance and flavor industry due to its pleasant odor and might also have potential applications in the pharmaceutical and cosmetic industries. However, it is important to handle this compound with care as it may be toxic if ingested or inhaled, and precautions should be taken when working with it in a laboratory or industrial setting.

Upstream product

• 50603-71-9 3-methoxycarbonyl-2H-cyclohepta[b]furan-2-one 
• 67-64-1 acetone 
• 77-76-9 2,2-dimethoxy-propane 
• 2916-31-6 2,2-dimethyl-1,3-dioxolane 
• 544-25-2 Cyclohepta-1,3,5-triene 
• 20577-61-1 methyl 2,4-dioxopentanoate 

Downstream Products

• 180129-07-1 1-fluoro-2-methylazulene 
• 503810-64-8 methyl 2-bromomethyl-3-cinnamoylazulene-1-carboxylate 
• 503810-54-6 methyl 3-cinnamoyl-2-methylazulene-1-carboxylate 
• 769-86-8 2-methylazulene 

Relevant articles and documents

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A practical approach for the preparation of monofunctional azulenyl squaraine dye

The synthesis of monofunctional azulenyl squaraine dye NIRQ700 is described. The essential azulene intermediate 3, 1-(methoxycarbonyl)-2-methylazulene, was achieved via [8+2] cycloaddition between lactone 2, 2H-3-methoxycarbonyl-cyclohepta[b]furan-2-one, and the in situ generated vinyl ethers under high temperature and pressure conditions. Methylation on the cycloheptatriene ring of 2-methyl azulene 6 via Meisenheimer-type intermediate following Schrott's method formed the carboxylic acid intermediate 9, 3-(2-methyl-azulen-4-yl)-propionic acid. Condensation of 9 with squaric acid provided the title compound NIRQ700 at moderate yields. The non-fluorescent squaraine dye NIRQ700 absorbed in a 600-700 nm range and potentially can be used to quench a number of available NIR fluorochromes in order to extend the spectrum of biological quenching assays.

Synthesis and Properties of Fluoroazulenes. II. Electrophilic Fluorination of Azulenes with N-Fluoro Reagents

1-Fluoro- and 1,3-difluoroazulenes were synthesized for the first time by the electrophilic fluorination of azulenes with N-fluoro reagents. Selective preparation of 1-fluoroazulenes were performed by the fluorination of methyl azulene-1-carboxylates, followed by demethoxycarbonylation in 100% H3PO4 2-Substituted azulenes were fluorinated in higher yields. In the 1HNMR of 1-fluoroazulene, long-range .JFH values were not observed at H-2 and H-8, in contrast to those for 1-fluoronaphthalene. The 1-fluorine atom causes significant bathochromic shifts in the visible absorption of azulene, due to the so-called +Iπ effect.