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

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

Uses

Used in Agricultural Applications:
Dieldrin is used as an insecticide for controlling crop pests. It is highly toxic to a wide range of insects, making it effective in protecting agricultural produce from infestations.
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. As a result, efforts are being made to phase out and eliminate the use of dieldrin in various industries, including agriculture, to mitigate its negative impact on the environment and human health.

Upstream product

• 118-75-2 chloranil 
• 63301-13-3 4-chloro-N-(4-hydroxyphenyl)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 
• 251645-37-1 C₁₈H₁₀Cl₆N₂O₄S₂ 
• 173097-12-6 2,3,5,5,6,6-Hexachloro-1,4-di-p-tolylsulfonylimino-2-cyclohexene 
• 106-50-3 1,4-phenylenediamine 
• 41595-29-3 N,N'-ditosyl-p-phenylenediamine 
• 173097-13-7 C₁₈H₈Cl₈N₂O₄S₂ 
• 141481-38-1 4-Chloro-N-[2,3,5,5,6,6-hexachloro-4-oxo-cyclohex-2-en-(Z)-ylidene]-benzenesulfonamide 
• 141481-37-0 2,3,5,5,6,6-hexachloro-4-<(p-tolylsulfonyl)imino>-2-cyclohexen-1-one 
• 51-78-5 p-aminophenol hydrochloride 
• 7782-50-5 chlorine 

Downstream Products

• 14569-51-8 2-anilino-3,5,5,6,6-pentachloro-cyclohex-2-ene-1,4-dione 
• 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 
• 118-75-2 chloranil 
• 118-74-1 hexachlorobenzene 
• 14614-78-9 phosphoric acid mono-pentachlorophenyl ester 

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.

Reactions of polychloro derivatives of semiquinoid compounds based on N-arylsulfonyl-p-quinonimines with N-containing heterocycles

Semiquinoid derivatives based on N-arylsulfonyl-p-benzoquinonimines treated with N-containing five-membered heterocycles are hydrolyzed and then eliminate Cl2 molecule. Among the N-containing five-membered heterocycles with a conjugated benzene ring only benzotriazole reacts with semiquinoid derivatives of N-arylsulfonyl-p-benzoquinonimines affording 2,3-di(benzotriazol-1-yl)-5,5,6,6-tetrachlorocyclohexene-1,4-dione which occurs as crystalline cis-and trans-isomers. The structure of the stable transisomer was established by X-ray diffraction study. N-Arylsulfonyl-p-naphthoquinonimines do not react with N-containing heterocycles.

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.

CHLORINATION OF p-ARENESULFONAMIDOPHENOLS AND N-(ARYLSULFONYL)-p-BENZOQUINONE

The chlorination of p-arenesulfonamidophenols and N-(arylsulfonyl)-p-benzoquinone imines leads to 4--2,3,5,5,6,6-hexachloro-2-cyclohexen-1-ones.N-(Arylsulfonyl)-2,3,5,6-tetrachloro-p-benzoquinone imines were prepared for the first time.As a result of the occurrence of a competing hydrolysis process, in some cases, as well as chlorination products chloranil and/or 2,3,5,5,6,6-hexachloro-2-cyclohexene-1,4-dione were isolated.