Hexachlorocyclopentadiene

Base Information

• Chemical Name: Hexachlorocyclopentadiene
• CAS No.: 77-47-4
• Molecular Formula: C5Cl6
• Molecular Weight: 272.773
• European Community (EC) Number: 201-029-3
• ICSC Number: 1096
• NSC Number: 9235
• UN Number: 2646
• UNII: IP6ATU242I
• DSSTox Substance ID: DTXSID2020688
• Nikkaji Number: J1.949F
• Wikipedia: Hexachlorocyclopentadiene
• Wikidata: Q408998
• ChEMBL ID: CHEMBL1526721
• Mol file: 77-47-4.mol

Synonyms:hexachlorocyclopentadiene

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Chemical Property of Hexachlorocyclopentadiene

Chemical Property:

• Appearance/Colour: clear to light yellow liquid
• Vapor Pressure: 0.0518mmHg at 25°C
• Melting Point: -10 C
• Refractive Index: 1.5640
• Boiling Point: 239 C
• Flash Point: 150 C
• Density: 1.702
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 271.810166
• Heavy Atom Count: 11
• Complexity: 234
• Transport DOT Label: Poison Inhalation Hazard

Purity/Quality:

Safty Information:

• Hazard Codes: T+:Very toxic
• Statements: R22:; R24:; R26:; R34:; R50/53:
• Safety Statements: S23:; S39:; S45:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Other Toxic Gases & Vapors
• Canonical SMILES: C1(=C(C(C(=C1Cl)Cl)(Cl)Cl)Cl)Cl
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation may cause lung oedema. The substance may cause effects on the kidneys and liver. This may result in tissue lesions. The effects may be delayed. Medical observation is indicated.
• General Description: Perchlorocyclopentadiene (hexachlorocyclopentadiene, HCP) is a chlorinated cyclopentadiene derivative used as a key intermediate in Diels-Alder reactions for synthesizing chlordane homologues and other polycyclic chlorinated compounds. In this study, HCP was reacted with cycloheptatriene and cycloheptadiene to form seven-ring chlordane analogues, though these products exhibited reduced insecticidal activity compared to traditional chlordane derivatives, likely due to structural asymmetry and increased molecular flexibility.

Technology Process of Hexachlorocyclopentadiene

There total 33 articles about Hexachlorocyclopentadiene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

2-bromo-3-iodo-bis(hexachlorocyclopentadiene)naphthalene (623924-91-4) → 2-bromo-3-iodonaphthalene (102153-44-6) + hexachlorocyclopentadiene (77-47-4)

Guidance literature:

at 210 ℃; for 2h; under 0.0112511 Torr; Pyrolysis;

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 1,2,3,4,5-pentachlorocyclopentadiene (25329-35-5) + hexachlorocyclopentadiene (77-47-4)

Guidance literature:

With alkaline aqueous sodium hypochlorite solution; Petroleum ether;

DOI:10.1007/BF00900102

Reference yield:

1,2,3,4-Tetrachloronaphthalene-Bis(hexachlorocyclopentadiene) Adduct (80789-64-6) → 1,2,3,4-tetrachloronaphthalene (20020-02-4) + hexachlorocyclopentadiene (77-47-4)

Guidance literature:

With air; In solid; Heating;

DOI:10.1021/jo00028a044

upstream raw materials:

cis-1,2-Dichloroethylene

perchloropropene

tetrachloromethane

Trichloroethylene

Downstream raw materials:

endo,exo-1,8,9,10,11,11-hexachloro-3,6-epoxytricyclo<6.2.1.0^2,7>undec-9-ene-4,5-dicarboxylic anhydride

1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-endo-cis-5,6-dicarboxylic acid

(+/-)-4.5.6.7.8.8-hexachloro-(3arH.7acH)-3a.4.7.7a-tetrahydro-4c.7c-methano-indene

(+/-)-1.2.3.4.5.6.7.8.10.10.11.11-dodecachloro-(4arH.4btH.8atH.9acH)-1.4.4a.4b.5.8.8a.9a-octahydro-1c.4c:5t.8t-dimethano-fluorene

Refernces

Concerning seven-ring-homologs in the chlordan series

10.1002/cber.19671000321

The study investigates the synthesis and insecticidal properties of seven-ring homologues in the chlordane series. The researchers used Diels-Alder addition reactions involving cycloheptatriene (CHT) and cycloheptadiene (CHD) with hexachlorocyclopentadiene (HCP) to produce tricyclododecene and other seven-ring analogues of chlordane. The structures of these compounds were confirmed through reactions, UV, and NMR spectroscopy. The study also explored various reactions and subsequent products of these chlordane homologues, discussing their insecticidal properties. Key compounds synthesized include 1,9.10.11.12.12-hexachlor-tricyclo[7.2.1.02.8]dodecen-(3.10) (3), which was obtained through heating compound 1 in dimethylformamide or xylene, and 1.9.10.11.12.12-hexachlor-tricyclo[7.2.1.02.8]dodecen-(3.10) (3), which was synthesized by heating compound 1 in absolute xylene. The study found that while these seven-ring homologues are similar to chlordane in structure, they exhibit significantly lower insecticidal efficacy, possibly due to the asymmetry of the tricyclododecane framework and increased molecular flexibility compared to the strained cyclopentane ring in chlordane derivatives.