Chlordane
| Names | |
|---|---|
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Systematic IUPAC name
1,2,4,5,6,7,8,8-Octachloro-3a,4,7,7a-tetrahydro-4,7-methanoindane
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| Other names
Chlordan; Chlordano; Ortho; Octachloro-4,7-methanohydroindane
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| Identifiers | |
57-74-9 
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| ECHA InfoCard | 100.000.317 |
| 2831 | |
| KEGG |
C14176
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| PubChem | 5993 |
| UNII |
A9RLM212CY
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| Properties | |
| C10H6Cl8 | |
| Molar mass | 409.76 g·mol−1 |
| Appearance | Colorless, viscous liquid |
| Odor | Slightly pungent, chlorine-like |
| Density | 1.60 g/cm3 |
| Melting point | 102–106 °C (216–223 °F; 375–379 K) |
| Boiling point | decomposes |
| 0.0001% (20°C) | |
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Refractive index (nD)
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1.565 |
| Hazards | |
| Main hazards | potential occupational carcinogen |
| Flash point | 107 °C (225 °F; 380 K) (open cup) |
| Explosive limits | 0.7–5% |
| Lethal dose or concentration (LD, LC): | |
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LD50 (median dose)
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590 mg/kg (rat, oral) 100 mg/kg (rabbit, oral) 430 mg/kg (mouse, oral) 300 mg/kg (rabbit, oral) 145 mg/kg (mouse, oral) 1720 mg/kg (hamster, oral) 200 mg/kg (rat, oral) |
| US health exposure limits (NIOSH): | |
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PEL (Permissible)
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TWA 0.5 mg/m3 [skin] |
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REL (Recommended)
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Ca TWA 0.5 mg/m3 [skin] |
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IDLH (Immediate danger)
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100 mg/m3 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
The name Chlordane, or chlordan, is commonly used as both a specific chemical (with trans-and cis- isomers) and as a mixture of compounds (main components- heptachlor, chlordane, and nonachlor). This mixture, more specifically called technical chlordane, was first produced in the 1940s by Julius Hyman. Technical chlordane development was by chance, during a search for possible uses of a by-product of synthetic rubber manufacturing. By chlorinating this by-product, persistent and potent insecticides were easily and cheaply produced. The chlorines, 7 in the case of heptachlor and 8 in chlordane, 9 in the case on nonachlor, surround and stabilize the cyclodiene ring and thus are referred to as cyclodienes. Other members of the cyclodiene family of organochorine insecticides are aldrin and its epoxide, dieldrin. This white solid was sold in the U.S. until 1988 as an insecticide for treating approximately 30 million homes for termites for crops like corn and citrus, and on lawns and domestic gardens. Technical grade chlordane is a complex mixture of over 120 structurally related chemical compounds.
Chlordane is one so-called cyclodiene pesticide, meaning that it is derived from hexachlorocyclopentadiene.
Hexachlorocyclopentadiene forms a Diels-Alder adduct with cyclopentadiene, and chlorination of this adduct gives predominantly two chlordane isomers, α and β, in addition to other products such as trans-nonachlor and heptachlor. The β-isomer is popularly known as gamma and is more bioactive. The mixture that is composed of 147 components is called technical chlordane.
cis-chlordane (also known as α-chlordane (CAS=5103-71-9))
trans-chlordane (also known as γ-chlordane and beta-chlordane (CAS=5103-74-2))
trans-nonachlor
(+)-heptachlor
It was sold in the United States from 1948 to 1988, both as a dust and an emulsified solution.
Because of concern about damage to the environment and harm to human health, the United States Environmental Protection Agency (EPA) banned all uses of chlordane in 1983, except termite control. The EPA banned all uses of chlordane in 1988. The EPA recommends that children should not drink water with more than 60 parts of chlordane per billion parts of drinking water (60 ppb) for longer than 1 day. EPA has set a limit in drinking water of 2 ppb.
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