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

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

Uses

Used in Organic Electronics:
TCNQ is utilized as a semiconducting material in the field of organic electronics, leveraging its unique electronic properties to enhance the performance of electronic devices.
Used in Materials Science:
In materials science, TCNQ serves as a key component in the creation of organic conductors and superconductors, contributing to the advancement of materials with improved electrical conductivity.
Used in Charge-Transfer Complexes:
TCNQ is employed in the formation of charge-transfer complexes, which are of significant interest in the study of molecular electronics due to their potential applications in developing new electronic devices and technologies.
Used in Molecular Electronics:
trans-2-Chloro-3-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthalenedione's role in molecular electronics is highlighted by its potential use in the development of molecular-scale electronic components, which could revolutionize the electronics industry by enabling the creation of smaller, more efficient devices.

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

• 36716-71-9 4-(4-chlorophenyl)-4-hydroxycyclohexanone 
• 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 
• 126991-59-1 8-(4-chlorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol 
• 98322-65-7 4-(4-Chloro-phenyl)-cyclohexanol 
• 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 

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.

A single-pot synthesis of atovaquone: An antiparasitic drug of choice

The present article relates to a practical, economically viable, and validated at industrial scale, single-pot synthetic route for preparation of atovaquone, one of the most versatile antiparasitic drugs of choice used for the prophylaxis and treatment of diseases such as pneumocystis, toxoplasmosis, babesiosis, coccidiosis, and malaria. However, owing to the extremely poor yields of synthesis and very high doses of treatment (due to poor bioavailability) the cost of treatment with this drug is not affordable by the patients in need, particularly in the third world countries where these diseases are most prevalent. Unlike most of the reported processes which use 2-chloronaphthoquinone and pure trans-4-chlorophenyl cyclohexane carboxylic acid, our process is based on the decarboxylative alkylation of isomeric mixture of 4-chlorophenyl cyclohexane carboxylic acid with 1,4-naphthoquinone to give 42% overall yield of atovaquone, 10 times higher than from the reported process (4%) from the innovators of this drug.

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 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.