18989-82-7

Basic information

• Product Name: 2,6-bis(4-chlorobenzylidene)cyclohexan-1-one
• Synonyms: 2,6-bis(4-chlorobenzylidene)cyclohexan-1-one;1,3-Bis(4-chlorobenzylidene)cyclohexane-2-one;2,6-Bis(4-chlorobenzylidene)cyclohexane-1-one;2,6-Bis(p-chlorobenzylidene)cyclohexanone;2,6-Bis[(4-chlorophenyl)methylene]cyclohexanone;2,6-Bis(4-chlorobenzylidene)cyclohexanone;Cyclohexanone, 2,6-bis((4-chlorophenyl)methylene)-;Einecs 242-725-7
• CAS NO: 18989-82-7
• Molecular Formula: C₂₀H₁₆Cl₂O
• Molecular Weight: 343.24644
• EINECS: 242-725-7
• Mol File: 18989-82-7.mol
• Article Data: 82

Chemical Properties

• Melting Point: 147-148 °C
• Boiling Point: 528.7°Cat760mmHg
• Flash Point: 220.4°C
• Appearance: /
• Density: 1.308g/cm³
• Vapor Pressure: 2.91E-11mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: 2,6-bis(4-chlorobenzylidene)cyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-bis(4-chlorobenzylidene)cyclohexan-1-one(18989-82-7)
• EPA Substance Registry System: 2,6-bis(4-chlorobenzylidene)cyclohexan-1-one(18989-82-7)

Safety Data

• Hazardous Substances Data: 18989-82-7(Hazardous Substances Data)

Usage

General Description

2,6-bis(4-chlorobenzylidene)cyclohexan-1-one, also known as Muscone, is a synthetic compound commonly used in perfumery for its musky fragrance. It is a cyclic ketone with two benzylidene groups, each containing a chlorine atom, attached to the cyclohexane ring. Muscone is highly valued for its long-lasting and animalic scent, often described as sweet, woody, and musky. Due to its intense fragrance, it is used as a base note in many high-end perfumes and colognes. Additionally, it has been studied for its potential pharmaceutical properties, and it is also used as a flavoring agent in foods and beverages.

InChI:InChI=1/C20H16Cl2O/c21-18-8-4-14(5-9-18)12-16-2-1-3-17(20(16)23)13-15-6-10-19(22)11-7-15/h4-13H,1-3H2

Upstream product

• 108-94-1 cyclohexanone 
• 104-88-1 4-chlorobenzaldehyde 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 13086-93-6 (acetyloxy)(4-chlorophenyl)methyl acetate 
• 1670-47-9 1,1-diethoxycyclohexane 

Downstream Products

• 110049-85-9 2,6-bis(4-chlorobenzyl)cyclohexanone 
• 94990-32-6 E-2-amino-4-(4-chlorophenyl)-8-(4'-chlorophenylmethylene)-5,6,7,8-tetrahydrobenzo[d]pyrimidine 
• 65331-28-4 (8E)-8-(4-chlorobenzylidene)-4-(4-chlorophenyl)-3,4,5,6,7,8-hexahydroquinazoline-2(1H)thione 

Relevant articles and documents

Design, synthesis and antimicrobial properties of novel 3,3a,4,5,6,7-hexahydroindazole and arylthiazolylpyrazoline derivatives

A remarkable diastereoselective synthesis of some novel arylthiazolyl pyrazoline derivatives 3(a-l) is displayed which were evaluated for their in vitro antimicrobial activities. In particular, compounds 3e, 3g & 3l (MIC 12.5 μg /ml) showed good activity against S. aureus and compounds 3b & 3j (MIC 12.5 μg / ml) against B. subtilis. Compounds 3g, 3i, 3j (MIC 12.5 μg/ ml) and 3l (MIC 6.25 μg / ml) also displayed excellent antifungal activity against C. albicans. Of all the synthesized compounds, 3g and 3e exerted a wide range of antibacterial activities against entire tested gram positive (S. aureus and B. subtilis) and gram negative (E. coli and P. aeruginosa) bacterial strain except P. aeruginosa.

Synthesis of thiazolylidenethiazoloquinazolinone hybrids from monocarbonyl curcumin analogues. Characterization, bio-evaluation and DFT study

Given the diverse pharmacological attributes possessed by the curcumin and its analogs, quinazolinethione 3, thiazoloquinazolinone 4, and thiazolylidene thiazoloquinazolinone hybrids D1-D12 were synthesized from α, α’ Bis(arylidene)Cyclohexanone (BAC) as starting material. The proposed structures of all synthesized compounds were confirmed by 1H, 13CNMR, and elemental analysis. The newly synthesized hybrids were screened in vitro for their antimicrobial and antioxidant activities. Preliminary studies showed that compounds D4, D5, D10, D11, and D12 exhibited superior inhibitory behaviors against some microorganisms in comparison with standard drugs. In addition, DPPH radical scavenging assay was used to evaluate their antioxidant property. Accordingly, compound D11 was found to be a more powerful antioxidant than the other compounds. Furthermore, the HOMO–LUMO energy values and some chemical parameters indicate that the synthesized hybrid D11 is more reactive than D7. These results were consistent with our experimental data on antioxidants. Moreover, molecular electrostatic potential (MEP) maps were computed in order to predict the reactive sites for nucleophilic and electrophilic attacks of the synthesized hybrids D7 and D11.

Green, rapid, and highly efficient syntheses of α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones as potentially biologic compounds via solvent-free microwave-assisted Claisen–Schmidt condensation catalyzed by MoCl5

A new, green, and highly efficient protocol for the expeditious preparation of some α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones via a simple microwave-assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent-free conditions, simple operation, use of a very inexpensive and available catalyst, low catalyst loading, short reaction times, high yields of the pure products, no harmful by-products, easy workup, and also the applicability of microwave irradiation as a clean source of energy. Furthermore, a gram-scale reaction was successfully conducted, proving the scalability of this current Claisen–Schmidt condensation reaction.