Aldrin

Aldrin
Names
	Preferred IUPAC name (1R,4S,4aS,5S,8R,8aR)-1,2,3,4,10,10-Hexachloro-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene
	Other names HHDN; octalene
Identifiers
CAS Number	309-00-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:2564;
ChEMBL	ChEMBL195953;
ChemSpider	10292747 ;
ECHA InfoCard	100.005.652
EC Number	206-215-8;
KEGG	C07552 ;
PubChem CID	2087;
RTECS number	IO2100000;
UNII	OZE3CLY605 ;
UN number	2762, 2761
CompTox Dashboard (EPA)	DTXSID8020040 ;
	InChI InChI=1S/C12H8Cl6/c13-8-9(14)11(16)7-5-2-1-4(3-5)6(7)10(8,15)12(11,17)18/h1-2,4-7H,3H2/t4-,5+,6+,7-,10+,11- Key: QBYJBZPUGVGKQQ-SJJAEHHWSA-N ; InChI=1/C12H8Cl6/c13-8-9(14)11(16)7-5-2-1-4(3-5)6(7)10(8,15)12(11,17)18/h1-2,4-7H,3H2/t4-,5+,6+,7-,10+,11- Key: QBYJBZPUGVGKQQ-SJJAEHHWBI;
	SMILES ClC4(Cl)[C@@]2(Cl)C(/Cl)=C(/Cl)[C@]4(Cl)[C@@H]3[C@@H]\1C[C@@H](/C=C/1)[C@H]23;
Properties
Chemical formula	C12H8Cl6
Molar mass	364.90 g·mol−1
Appearance	Colorless solid
Density	1.60 g/mL
Melting point	104 °C (219 °F; 377 K)
Solubility in water	slightly soluble (0.003%)
Vapor pressure	7.5 × 10−5 mmHg @ 20 °C
Pharmacology
Legal status	AU: S6 (Poison);
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	potential occupational carcinogen
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H301, H310, H311, H351, H372, H410
Precautionary statements	P201, P202, P260, P262, P264, P270, P273, P280, P281, P301+P310, P302+P350, P302+P352, P308+P313, P310, P312, P314, P321, P322, P330, P361, P363, P391, P405, P501
NFPA 704 (fire diamond)	4 0 0
Flash point	66 °C (151 °F; 339 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	50 mg/kg (rabbit, oral); 33 mg/kg (guinea pig, oral); 39 mg/kg (rat, oral); 44 mg/kg (mouse, oral)
LCLo (lowest published)	5.8 mg/m3 (rat, 4 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.25 mg/m3 [skin]
REL (Recommended)	Ca TWA 0.25 mg/m3 [skin]
IDLH (Immediate danger)	25 mg/m3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Aldrin is an organochlorine insecticide that was widely used until the 1990s, when it was banned in most countries. Aldrin is a member of the so-called "classic organochlorines" (COC) group of pesticides. COCs enjoyed a very sharp rise in popularity during and after World War II. Other noteworthy examples of COCs include dieldrin and DDT.^[3] After research showed that organochlorines can be highly toxic to the ecosystem through bioaccumulation, most were banned from use. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides (a term for pesticides derived from Hexachlorocyclopentadiene) became notorious as persistent organic pollutants.^[4]

^ ^a ^b ^c ^d ^e ^f ^g ^h NIOSH Pocket Guide to Chemical Hazards. "#0016". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "Aldrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Zitko, Vladimir (2003), "Chlorinated Pesticides: Aldrin, DDT, Endrin, Dieldrin, Mirex", in Fiedler, H. (ed.), Persistent Organic Pollutants, The Handbook of Environmental Chemistry, vol. 3O, Springer Berlin Heidelberg, pp. 47–90, doi:10.1007/10751132_4, ISBN 9783540479321
^ Robert L. Metcalf "Insect Control" in Ullmann’s Encyclopedia of Industrial Chemistry" Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a14_263

[NIOSH-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h NIOSH Pocket Guide to Chemical Hazards. "#0016". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-2] "Aldrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[3] Zitko, Vladimir (2003), "Chlorinated Pesticides: Aldrin, DDT, Endrin, Dieldrin, Mirex", in Fiedler, H. (ed.), Persistent Organic Pollutants, The Handbook of Environmental Chemistry, vol. 3O, Springer Berlin Heidelberg, pp. 47–90, doi:10.1007/10751132_4, ISBN 9783540479321

[Ullmann-4] Robert L. Metcalf "Insect Control" in Ullmann’s Encyclopedia of Industrial Chemistry" Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a14_263

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Names


Preferred IUPAC name (1R,4S,4aS,5S,8R,8aR)-1,2,3,4,10,10-Hexachloro-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene
Other names HHDN^[1] octalene^[1]
Identifiers
CAS Number	309-00-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:2564
ChEMBL	ChEMBL195953
ChemSpider	10292747^Y
ECHA InfoCard	100.005.652
EC Number	206-215-8
KEGG	C07552^Y
PubChem CID	2087
RTECS number	IO2100000
UNII	OZE3CLY605^Y
UN number	2762, 2761
CompTox Dashboard (EPA)	DTXSID8020040
InChI InChI=1S/C12H8Cl6/c13-8-9(14)11(16)7-5-2-1-4(3-5)6(7)10(8,15)12(11,17)18/h1-2,4-7H,3H2/t4-,5+,6+,7-,10+,11-^Y Key: QBYJBZPUGVGKQQ-SJJAEHHWSA-N^Y InChI=1/C12H8Cl6/c13-8-9(14)11(16)7-5-2-1-4(3-5)6(7)10(8,15)12(11,17)18/h1-2,4-7H,3H2/t4-,5+,6+,7-,10+,11- Key: QBYJBZPUGVGKQQ-SJJAEHHWBI
SMILES ClC4(Cl)[C@@]2(Cl)C(/Cl)=C(/Cl)[C@]4(Cl)[C@@H]3[C@@H]\1C[C@@H](/C=C/1)[C@H]23
Properties
Chemical formula	C₁₂H₈Cl₆
Molar mass	364.90 g·mol⁻¹
Appearance	Colorless solid
Density	1.60 g/mL^[1]
Melting point	104 °C (219 °F; 377 K)
Solubility in water	slightly soluble (0.003%)^[1]
Vapor pressure	7.5 × 10⁻⁵ mmHg @ 20 °C
Pharmacology
Legal status	AU: S6 (Poison)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	potential occupational carcinogen^[1]
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H301, H310, H311, H351, H372, H410
Precautionary statements	P201, P202, P260, P262, P264, P270, P273, P280, P281, P301+P310, P302+P350, P302+P352, P308+P313, P310, P312, P314, P321, P322, P330, P361, P363, P391, P405, P501
NFPA 704 (fire diamond)	4 0 0
Flash point	66 °C (151 °F; 339 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	50 mg/kg (rabbit, oral) 33 mg/kg (guinea pig, oral) 39 mg/kg (rat, oral) 44 mg/kg (mouse, oral)^[2]
LC_Lo (lowest published)	5.8 mg/m³ (rat, 4 hr)^[2]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.25 mg/m³ [skin]^[1]
REL (Recommended)	Ca TWA 0.25 mg/m³ [skin]^[1]
IDLH (Immediate danger)	25 mg/m³^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references