Aldrin

For other uses, see Aldrin (disambiguation).
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[1]
octalene[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.652 Edit this at Wikidata
EC Number
  • 206-215-8
KEGG
RTECS number
  • IO2100000
UNII
UN number 2762, 2761
  • 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- checkY
    Key: QBYJBZPUGVGKQQ-SJJAEHHWSA-N checkY
  • 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
  • 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
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)
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
 Toxic and is a suspected human carcinogen[1]
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H300, H301, H310, H311, H351, H372, H410
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)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
0
0
Flash point 66 °C (151 °F; 339 K)
Lethal dose or concentration (LD, LC):
50 mg/kg (rabbit, oral)
33 mg/kg (guinea pig, oral)
39 mg/kg (rat, oral)
44 mg/kg (mouse, oral)[2]
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).
checkY verify (what is checkY☒N ?)

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]

  1. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0016". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "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
  4. ^ Robert L. Metcalf "Insect Control" in Ullmann’s Encyclopedia of Industrial Chemistry" Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a14_263