14504-09-7

Basic information

• Product Name: 2,3,5,5,6,6-hexachlorocyclohex-2-ene-1,4-dione
• CAS NO: 14504-09-7
• Molecular Formula: C₆Cl₆O₂
• Molecular Weight: 316.781
• Mol File: 14504-09-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 290.5°C at 760 mmHg
• Flash Point: 121.4°C
• Density: 1.89g/cm³
• Vapor Pressure: 0.00206mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 2,3,5,5,6,6-hexachlorocyclohex-2-ene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,5,6,6-hexachlorocyclohex-2-ene-1,4-dione(14504-09-7)
• EPA Substance Registry System: 2,3,5,5,6,6-hexachlorocyclohex-2-ene-1,4-dione(14504-09-7)

Safety Data

• Hazardous Substances Data: 14504-09-7(Hazardous Substances Data)

Usage

General Description

2,3,5,5,6,6-hexachlorocyclohex-2-ene-1,4-dione is a chemical compound that belongs to the group of chlorinated hydrocarbons. It is an organic compound with the molecular formula C6H6Cl6O2. 2,3,5,5,6,6-hexachlorocyclohex-2-ene-1,4-dione is also known as "dieldrin" and is primarily used as an insecticide. Dieldrin is highly toxic to a wide range of insects and has been used extensively in agriculture to control crop pests. However, due to its persistent nature and harmful effects on the environment and human health, its use has been heavily restricted or banned in many countries. Dieldrin is also classified as a persistent organic pollutant (POP) and is a potential carcinogen. Due to its toxic nature and negative impact on the environment, efforts are being made to phase out and eliminate the use of dieldrin.

Upstream product

• 118-75-2 chloranil 
• 4056-56-8 N-(phenylsulfonyl)-1,4-benzoquinone monoimine 
• 59876-73-2 N-p-methylbenzenesulfonyl-2,6-dichloro-1,4-benzoquinone imine 
• 63301-13-3 4-chloro-N-(4-hydroxyphenyl)benzenesulfonamide 
• 37051-70-0 4-methyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenesulfonamide 
• 38250-73-6 4-chloro-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenesulfonamide 
• 1146-43-6 N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide 
• 59876-72-1 N-(3,5-dichloro-4-hydroxyphenyl)-p-toluenesulfonamide 
• 41595-29-3 N,N'-ditosyl-p-phenylenediamine 
• 141481-37-0 2,3,5,5,6,6-hexachloro-4-<(p-tolylsulfonyl)imino>-2-cyclohexen-1-one 
• 251645-37-1 C₁₈H₁₀Cl₆N₂O₄S₂ 
• 173097-12-6 2,3,5,5,6,6-Hexachloro-1,4-di-p-tolylsulfonylimino-2-cyclohexene 
• 7647-01-0 hydrogenchloride 
• 51-78-5 p-aminophenol hydrochloride 

Downstream Products

• 14614-78-9 phosphoric acid mono-pentachlorophenyl ester 
• 14569-51-8 2-anilino-3,5,5,6,6-pentachloro-cyclohex-2-ene-1,4-dione 
• 118-75-2 chloranil 
• 7647-01-0 hydrogenchloride 
• 608-42-4 cis-2,3-dichlorobutenedioic acid 
• 79-01-6 Trichloroethylene 
• 87-87-6 2,3,5,6-tetrachlorobenzene-1,4-diol 
• 118-74-1 hexachlorobenzene 

Relevant articles and documents

Reaction of semiquinoid compounds derived from N-arylsulfonyl-p-quinonemono- and diimines with tosylhydrazine

Reaction of 4-arylsulfonylimino-2,3,5,6,6-pentachloro-2-cyclohexen-1-ones with tosylhydrazine gives rise to N-arylsulfonyl-N-p-tolylsulfonyl-2,3,5,6-tetrachloroaminophenols. With 4-arylsulfonylimino-2,2,3-trichloro-1,2,3,4-tetrahydronaphthalen-1-ones and 4-arylsulfonylimino-2-dihalo-1,2,3,4-tetrahydronaphthalen-1-ones reaction products are 4-arylsulfonylamido-2,3-dichloro-4-p-tolylsulfonylhydrazido-1,4-dihydronaphthalen-1-ones and 2-p-tolylsulfonyl-1,4-naphthoquinone-4-diazide respectively. First stage of the processes consists in dehydrohalogenation yielding the corresponding N-arylsulfonyl-p-quinonimines.

CHLORINATION OF N,N'-BISARYLSULFONYL-1,4-PHENYLENEDIAMINES AND N,N'-BISARYLSULFONYL-1,4-BENZOQUINONE DIIMINES

The chlorination of N,N'-bisarylsulfonyl-1,4-phenylenediamines leads to 1,4-bisarylsulfonylimino-2,3,5,5,6,6-hexachloro-2-cyclohexenes.Together with the chlorination products chloranil and/or 2,3,5,5,6,6-hexachloro-1,2-cyclohexene-1,4-dione were isolated as a result of the competing hydrolysis process.