7508-12-5

Basic information

• Product Name: 2,3-dimethyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one
• CAS NO: 7508-12-5
• Molecular Formula: C₁₃H₁₆O
• Molecular Weight: 188.2655
• Mol File: 7508-12-5.mol

Chemical Properties

• Boiling Point: 335°C at 760 mmHg
• Flash Point: 144.9°C
• Density: 1.028g/cm³
• Vapor Pressure: 0.000123mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 2,3-dimethyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dimethyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one(7508-12-5)
• EPA Substance Registry System: 2,3-dimethyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one(7508-12-5)

Safety Data

• Hazardous Substances Data: 7508-12-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3-dimethyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one is used as a key intermediate in organic synthesis for the creation of a variety of complex organic molecules. Its unique structure allows it to serve as a building block for the development of new compounds with specific properties.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,3-dimethyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one is utilized as a precursor in the synthesis of certain drugs. Its complex structure contributes to the development of pharmaceuticals with targeted therapeutic effects, potentially leading to the creation of novel treatments for various medical conditions.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, 2,3-dimethyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one is employed as a starting material for the synthesis of specific agrochemicals. Its role in this industry is crucial for the development of effective pesticides, herbicides, and other agricultural products that enhance crop protection and yield.
Due to the complex structure of 2,3-dimethyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one, it necessitates careful handling and the application of precise synthesis techniques to ensure the successful creation of desired end products in these industries.

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 108-55-4 glutaric anhydride, 
• 7508-13-6 5-(3,4-dimethyl-phenyl)-5-oxo-valeric acid 
• 95-47-6 o-xylene 
• 5205-39-0 ethyl glutaroyl chloride 
• 107272-51-5 2,3-dimethyl-6,7,8,9-tetrahydro-benzocyclohepten-5-one oxime 
• 35872-49-2 5-(3,4-dimethyl-phenyl)-valeric acid 

Downstream Products

• 1609188-54-6 2,3-dimethyl-5-(2-methoxyphenyl)-8,9-dihydro-7H-benzocycloheptene-6-carbaldehyde 
• 1609188-57-9 2,3-dimethyl-5-(2-methoxyphenyl)-8,9-dihydro-7H-benzocycloheptene-6-carboxylic acid 

Relevant articles and documents

Iridium/f-Amphol-catalyzed Efficient Asymmetric Hydrogenation of Benzo-fused Cyclic Ketones

Iridium/f-Amphol-catalyzed asymmetric hydrogenation of various benzo-fused five to seven-membered cyclic ketones was successfully developed, affording a series of chiral benzo-fused cyclic alcohols with excellent results (75%–99% yields, 93%–>99% ee, and TON up to 297 000). The enantioenriched products can be employed as key intermediates or motifs for the synthesis of some important biologically active compounds, such as rasagiline mesylate TVP-1012 used for the treatment of Parkinson's disease, the enantiomer of anticonvulsant drug eslicarbazepine acetate (BIA 2-093). (Figure presented.).

Design, synthesis and in vitro anti-tuberculosis activity of benzo[6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole derivatives

A series of novel benzo[6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole hybrids (7a–j & 8a–j) have been designed and synthesized in excellent yields by Huisgen's [3+2] cyclo addition reaction of 3-(azidomethyl)-2-methyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine (5) with various alkynes 6 in presence of copper sulphate and sodium ascorbate and their structures were confirmed by IR, 1H NMR, 13C NMR and HRMS. The newly synthesized compounds 7a–j & 8a–j were evaluated for their in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC 27294). Among the compounds tested, the compounds 7i and 8g displayed most potent activity with MIC value of 1.56 μg/mL with low cytotoxicity.

Three-component, one-pot synthesis of benzo[6,7]cyclohepta[1,2-b]pyridine derivatives under catalyst free conditions and evaluation of their anti-inflammatory activity

An efficient three-component protocol is described for the synthesis of benzo[6,7]cyclohepta[1,2-b]pyridine derivatives using β-chloroacroleins, 1,3-dicarbonyls and ammonium acetate under catalyst free conditions by using ethanol as reaction media. The mild reaction conditions, operational simplicity and high yields are the advantages of this protocol and the broad scope of this one-pot reaction makes this procedure promising for practical usages. All the final compounds were screened for anti-inflammatory activity. Among the compounds tested, the compounds 5a, 5b, 5c, 5d, 5f, and 5k exhibited significant inhibition of IL-1β and MCP-1 secretion as a measure of anti-inflammatory activity.

Synthesis of novel building blocks of benzosuberone bearing coumarin moieties and their evaluation as potential anticancer agents

A series of novel benzosuberone bearing coumarin moieties 5a-c have been synthesized and their structures were determined by analytical and spectral (FT-IR, 1H NMR, 13C NMR, HRMS) studies. The newly synthesized compounds were evaluated for their cytotoxicity against four human cancer cell lines, A549 (Human alveolar adenocarcinoma cell line), HeLa (Human cervical cancer cell line), MDA-MB-231 (Human breast adenocarcinoma cell line), MCF-7 (Human breast adenocarcinoma cell line) and normal cell line HEK293 (Human embryonic kidney cell line). Compound 5a exhibited promising cytotoxicity with IC50 values ranging from 3.35 to 16.79 μM against all the cancer cell lines like A549, HeLa, MCF-7 and MDA-MB-231, while compound 5c showed significant cytotoxicity against HeLa and MDA-MB-231 with IC50 values of 6.72 and 4.87, respectively.

Oxidative deoximation with H2O2 and MCM-41

A simple and mild method of oxidative deoximation with 30%H 2O2 and MCM-41 is described. This method is effective for deprotection of ketones and aldehydes.