1071223-07-8

Basic information

• Product Name: cis-2-(4-(4'-chlorophenyl)cyclohexyl)-3-chloronaphthalene-1,4-dione
• Synonyms: cis-2-(4-(4'-chlorophenyl)cyclohexyl)-3-chloronaphthalene-1,4-dione
• CAS NO: 1071223-07-8
• Molecular Weight: 385.29
• Mol File: 1071223-07-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: cis-2-(4-(4'-chlorophenyl)cyclohexyl)-3-chloronaphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: cis-2-(4-(4'-chlorophenyl)cyclohexyl)-3-chloronaphthalene-1,4-dione(1071223-07-8)
• EPA Substance Registry System: cis-2-(4-(4'-chlorophenyl)cyclohexyl)-3-chloronaphthalene-1,4-dione(1071223-07-8)

Safety Data

• Hazardous Substances Data: 1071223-07-8(Hazardous Substances Data)

Upstream product

• 129719-64-8 2-[4-(4-chlorophenyl)-cyclohexyl]-3-chloro-1,4-naphthoquinone 
• 98322-65-7 4-(4-Chloro-phenyl)-cyclohexanol 
• 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 
• 215672-87-0 Oxalic acid mono-[4-(4-chloro-phenyl)-cyclohexyl] ester 
• 36716-71-9 4-(4-chlorophenyl)-4-hydroxycyclohexanone 
• 14472-80-1 4-(4-chlorophenyl)cyclohexan-1-one 
• 637-87-6 1-Chloro-4-iodobenzene 
• 4746-97-8 cyclohexanedione monoethylene ketal 

Downstream Products

• 153977-22-1 trans-2-(4-(4'-chlorophenyl)cyclohexyl)-3-chloronaphthalene-1,4-dione 
• 137732-39-9 cis-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione 

Relevant articles and documents

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.

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.