18989-81-6

Basic information

• Product Name: 2,6-bis(o-chlorobenzylidene)cyclohexan-1-one
• Synonyms: 2,6-bis(o-chlorobenzylidene)cyclohexan-1-one;2,6-Bis[(2-chlorophenyl)methylene]cyclohexanone;Einecs 242-724-1
• CAS NO: 18989-81-6
• Molecular Formula: C₂₀H₁₆Cl₂O
• Molecular Weight: 343.24644
• EINECS: 242-724-1
• Mol File: 18989-81-6.mol
• Article Data: 38

Chemical Properties

• Boiling Point: 523.6°C at 760 mmHg
• Flash Point: 218.5°C
• Appearance: /
• Density: 1.308g/cm³
• Vapor Pressure: 4.65E-11mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: 2,6-bis(o-chlorobenzylidene)cyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-bis(o-chlorobenzylidene)cyclohexan-1-one(18989-81-6)
• EPA Substance Registry System: 2,6-bis(o-chlorobenzylidene)cyclohexan-1-one(18989-81-6)

Safety Data

• Hazardous Substances Data: 18989-81-6(Hazardous Substances Data)

Usage

General Description

2,6-bis(o-chlorobenzylidene)cyclohexan-1-one, also known as BCC, is a chemical compound that belongs to the group of aromatic ketones. It is a yellow crystalline solid with a molecular formula of C20H16Cl2O. BCC is used in various industrial applications, including as a fragrance ingredient in perfumes, as a flavoring agent in food products, and as a chemical intermediate in the production of pharmaceuticals and other organic compounds. It is also known to have potential pharmaceutical properties, including anti-inflammatory and antimicrobial activities. However, BCC is a known irritant and should be handled with caution, as it can cause skin and eye irritation upon contact.

InChI:InChI=1/C20H16Cl2O/c21-18-10-3-1-6-14(18)12-16-8-5-9-17(20(16)23)13-15-7-2-4-11-19(15)22/h1-4,6-7,10-13H,5,8-9H2

Upstream product

• 108-94-1 cyclohexanone 
• 89-98-5 2-chloro-benzaldehyde 
• 1670-47-9 1,1-diethoxycyclohexane 

Downstream Products

• 129116-59-2 1-(2-Chloro-phenyl)-5-[1-(2-chloro-phenyl)-meth-(E)-ylidene]-3-oxo-1,2,3,5,6,7,8,8a-octahydro-naphthalene-2-carboxylic acid (2-chloro-phenyl)-amide 
• 220981-18-0 (E)-1-(7-(2-chlorobenzylidene)-3-(2-chlorophenyl)-3,3a,4,-5,6,7-hexahydro-2H-indazol-2-yl)ethanone 
• 1428649-18-6 11-(2-chlorobenzylidene)-7-(2-chlorophenyl)-8,9,10,11-tetrahydro-6H,7H-chromeno[4,3-b]chromen-6-one 
• 94990-33-7 4-(2-Chloro-phenyl)-8-[1-(2-chloro-phenyl)-meth-(E)-ylidene]-5,6,7,8-tetrahydro-quinazolin-2-ylamine 

Relevant articles and documents

Synthesis, spectral analysis and quantum chemical studies on molecular geometry of (2E,6E)-2,6-bis(2-chlorobenzylidene)cyclohexanone: Experimental and theoretical approaches

(2E,6E)-2,6-bis(2-chlorobenzylidene) cyclohexanone was synthesized and characterized by proton and carbon nuclear magnetic resonance, infrared, ultraviolet-visible, mass spectral analysis and X-ray crystallography techniques. Quantum Chemical calculations were done using Becke3-Lee-Yang-Parr with 6-31, 6-311, 6-311 + and 6-311++G (d, p) as basis sets and CAM-B3LYP with 6-31G(d,p) as the basis set. A good correlation between calculated and experimental spectroscopic data has been accomplished. Ultraviolet-Visible spectrum of the molecule was recorded in the region 200-500 nm and the electronic properties and composition were obtained using Time Dependent Density Functional Theory method. X-ray parameters (bonds, bond angles and torsion angles), Electric dipole moment, Mulliken atomic charges, polarizability and first static hyperpolarizability values have been calculated. Hyperconjugative interactions were studied with the help of natural bond orbital analysis. The thermodynamic properties of the compound were calculated at different temperatures.

Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water

A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields.

Antiparasitic activity of synthetic curcumin monocarbonyl analogues against Trichomonas vaginalis

Trichomoniasis is a parasitic infection caused by Trichomonas vaginalis and it is considered to be the most common non-viral sexually transmitted infection in the world. Since the 1960s, nitroimidazoles such as metronidazole are the drugs of choice for the treatment of trichomoniasis, but many adverse effects and allergic reactions may result from their use. Reports of metronidazole-resistant infections also highlight the importance for the search of new anti-T. vaginalis agents. Considering this, herein we report the anti-T. vaginalis evaluation of 21 synthetic monocarbonyl analogues of curcumin, which itself has been reported to possess antiparasitic potential. From the in vitro analysis of the synthetic molecules, untreated trophozoites, and metronidazole at 100 μM, it was observed that three curcumin analogues (3a, 3e, and 5e) exhibited anti-T. vaginalis activity comparable to metronidazole (no significant statistical difference). Optimal antiparasitic concentrations were determined to be 80 μM and 90 μM for propanone derivatives 3a and 3e, respectively, and 200 μM for cyclohexanone derivative 5e. Kinetic growth curves showed that, after 24 h, the trophozoites were completely inhibited. At the tested concentrations, natural curcumin did not significantly inhibit the growth of trophozoites, therefore demonstrating that the designed synthetic molecules not only have better chemical stability, but also higher anti-T. vaginalis potential. Cytotoxicity analysis, performed on VERO cells, demonstrated low, moderate and high cytotoxic effects for analogues 3e, 5e and 3a, respectively. This study suggests that these analogues possess chemical features of interest to be further explored as alternatives for the treatment of trichomoniasis.