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Usage

Uses

Used in Fragrance and Flavor Industry:
METHYL-2-METHYLAZULENE-1-CARBOXYLATE is used as a fragrance and flavoring agent due to its pleasant odor. Its aromatic properties make it a valuable component in creating various scents and flavors for consumer products.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, METHYL-2-METHYLAZULENE-1-CARBOXYLATE might have potential applications in the pharmaceutical industry, possibly due to its chemical structure and properties that could be harnessed for medicinal purposes.
Used in Cosmetic Industry:
Similarly, METHYL-2-METHYLAZULENE-1-CARBOXYLATE may also find use in the cosmetic industry, where its aromatic properties could be utilized in the formulation of scented products such as perfumes, lotions, and other personal care items.
Safety Precautions:
It is important to handle METHYL-2-METHYLAZULENE-1-CARBOXYLATE with care, as it may be toxic if ingested or inhaled. Appropriate safety measures should be taken when working with METHYL-2-METHYLAZULENE-1-CARBOXYLATE in laboratory or industrial settings to minimize health risks.

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

Synthesis of methyl 2-methylazulene-3-carboxylate in the presence of molecular sieves and reaction with N-bromosuccinimide

The preparation of methyl 2-methylazulene-1-carboxylate (1) was carried out in the presence of molecular sieves to obtain a good yield. The product was subjected to bromination under different reaction conditions to obtain methyl 1-bromo-2-methylazulene-1-carboxylate (2) and methyl 1-bromo-2-(bromomethyl) azulene-1-carboxylate (3). Copyright Taylor & Francis Group, LLC.

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.

Intermolecular [8+2] cycloaddition reactions of 2H-3-methoxycarbonylcyclohepta[b]furan-2-one with vinyl ethers: An approach to bicyclo[5.3.0]azulene derivatives

Substituted bicyclo[5.3.0]azulene compounds are synthesized by intermolecular [8+2] cycloaddition reactions of lactone 1 with vinyl ethers - acetal decomposition products - are described. The reactions were found to be temperature and solvent dependent.

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.

A CONVENIENT, ONE-POT AZULENE SYNTHESIS FROM CYCLOHEPTAFURAN-2-ONES AND VINYL ETHER AND ITS ANALOGUES. (II). ACETALS AS REAGENT

Variously functionalized azulene derivatives were synthesized in one-pot and by the reaction of cycloheptafuran-2-ones with acetals of several aldehydes and ketones on heating at 160-190 deg C in neat or aprotic solvent.