153977-22-1

Basic information

• Product Name: trans-2-Chloro-3-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthalenedione
• Synonyms: TRANS-2-CHLORO-3-[4-(4-CHLOROPHENYL)CYCLOHEXYL]-1,4-NAPHTHOQUINONE;trans-2-Chloro-3-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthalenedione;2-chloro-3-[4-(4-chlorophenyl)cyclohexyl]naphthalene-1,4-dione
• CAS NO: 153977-22-1
• Molecular Formula: C22H18Cl2O2
• Molecular Weight: 385.28
• Mol File: 153977-22-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 517.4 °C at 760 mmHg
• Flash Point: 216.1 °C
• Appearance: /
• Density: 1.34
• Vapor Pressure: 8.25E-11mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: trans-2-Chloro-3-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthalenedione(CAS DataBase Reference)
• NIST Chemistry Reference: trans-2-Chloro-3-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthalenedione(153977-22-1)
• EPA Substance Registry System: trans-2-Chloro-3-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthalenedione(153977-22-1)

Safety Data

• Hazardous Substances Data: 153977-22-1(Hazardous Substances Data)

Usage

General Description

Trans-2-Chloro-3-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthalenedione, also known as TCNQ, is a chemical compound with potential applications in organic electronics and materials science. It is a naphthalene derivative that contains two chloro substituents and a cyclohexyl ring attached to the naphthalene core. TCNQ has been studied for its semiconducting properties and has been used in the development of organic conductors and superconductors. It is also known for its role in charge-transfer complexes and has been investigated for its potential use in molecular electronics. The compound's unique structure and electronic properties make it a subject of ongoing research in the field of organic chemistry and materials science.

InChI:InChI=1/C22H18Cl2O2/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)22(26)18-4-2-1-3-17(18)21(19)25/h1-4,9-13,15H,5-8H2

Upstream product

• 129719-64-8 2-[4-(4-chlorophenyl)-cyclohexyl]-3-chloro-1,4-naphthoquinone 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 95233-37-7 (+/-)-trans-4-(4-chlorophenyl)cyclohexane carboxylic acid 
• 1203609-10-2 cis-2-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthoquinone 
• 14472-80-1 4-(4-chlorophenyl)cyclohexan-1-one 
• 637-87-6 1-Chloro-4-iodobenzene 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 215672-87-0 Oxalic acid mono-[4-(4-chloro-phenyl)-cyclohexyl] ester 
• 1100053-59-5 2-[4-(4-chlorophenyl)cyclohexyl]-2,3-dichloro-2,3-dihydro-1,4-naphthoquinone 
• 1100053-58-4 trans-2-[4-(4-cyclohexyl)chlorophenyl]-1,4-naphthoquinone 
• 98322-65-7 4-(4-Chloro-phenyl)-cyclohexanol 
• 36716-71-9 4-(4-chlorophenyl)-4-hydroxycyclohexanone 
• 126991-59-1 8-(4-chlorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol 

Downstream Products

• 137732-39-9 cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione 
• 95233-18-4 atovaquone 

Relevant articles and documents

Synthesis of atovaquone

A short synthesis of atovaquone I is achieved via the radical coupling of the trans-1,4-substituted cyclohexyl mono-oxalate 2 and 2- chloronapthoquinone under phase transfer conditions.

PROCESS FOR THE EPIMERIZATION OF ATOVAQUONE ISOMER, ATOVAQUONE INTERMEDIATES AND MIXTURE THEREOF

Provided is a process for the epimerization of the cis isomer of atovaquone, atovaquone intermediates and isomeric mixtures thereof into their corresponding trans-isomers resulting in higher yield of pure atovaquone.

PROCESS FOR PREPARATION OF ATOVAQUONE AND THE CONVERSION OF CIS-ISOMER TO TRANS- ISOMER

Substantially pure atovaquone and parocess for the preparation thereof is disclosed.