Aldrin

Aldrin

Names
IUPAC name 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 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
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
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	potential occupational carcinogen
GHS labelling:
Pictograms	Template:GHS06Template:GHS08Template:GHS09
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).
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Infobox references

Aldrin is an insecticide, which was used against termites, locusts and the larvae of Click beetles. Most plants and animals convert it to Dieldrin. It is listed in the Stockholm Convention on Persistent Organic Pollutants, its production, use and trade are banned since 2004. Aldrin is a neurotoxin. People inhaling it can develop headaches, but also seizures. In humans, Aldrin is converted to dieldrin in the liver. The change will mean that it can leave the body again. The problem is that the change is slow, and the half-life is about a year. Aldrin may be a teratogen, and it probably causes cancer.

Production

Aldrin is produced by combining hexachlorocyclopentadiene with norbornadiene in a Diels-Alder reaction to give the adduct.

Synthesis of Aldrin via a Diels-Alder reaction

Aldrin is named after the German chemist Kurt Alder, one of the coinventors of this kind of reaction. An estimated 270 million kilograms of aldrin and related cyclodiene pesticides were produced between 1946 and 1976.

In soil, on plant surfaces, or in the digestive tracts of insects, aldrin oxidizes to the epoxide, dieldrin. Dieldrin is more strongly insecticidal than aldrin.