View source for Dieldrin

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460784423
| Name = Dieldrin
| ImageFile1 = Dieldrin-3D-balls.png
| ImageFile2 = Dieldrin.svg
| ImageName = Dieldrin
| IUPACName = (1a''R'',2''R'',2a''S'',3''S'',6''R'',6a''R'',7''S'',7a''S'')-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-''b'']oxirene
| OtherNames = Dieldrin, HEOD
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = I0246D2ZS0
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10292746
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 481118
| InChI = 1/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2/t2-,3+,4+,5-,6-,7+,10+,11-
| InChIKey = DFBKLUNHFCTMDC-PICURKEMBL
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2/t2-,3+,4+,5-,6-,7+,10+,11-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DFBKLUNHFCTMDC-PICURKEMSA-N
| CASNo = 60-57-1
| CASNo_Ref = {{cascite|correct|CAS}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C13718
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 34696
| SMILES = ClC5(Cl)[C@]3(Cl)C(\Cl)=C(\Cl)[C@@]5(Cl)[C@H]4[C@H]1C[C@H]([C@@H]2O[C@H]12)[C@@H]34
| PubChem = 969491
}}
|Section2={{Chembox Properties
| C=12 | H=8 | Cl=6 | O=1
| MolarMass = 380.91 g/mol
| Density = 1.75 g/cm<sup>3</sup>
| MeltingPtC = 176 to 177
| MeltingPt_notes = 
| BoilingPtC = 385
| Appearance = colorless to light tan crystals
| Solubility = 0.02%<ref name=PGCH/>
  }}
|Section7={{Chembox Hazards
| PEL = TWA 0.25 mg/m<sup>3</sup> [skin]<ref name=PGCH>{{PGCH|0206}}</ref>
| IDLH = Ca [50 mg/m<sup>3</sup>]<ref name=PGCH/>
| REL = Ca TWA 0.25 mg/m<sup>3</sup> [skin]<ref name=PGCH/>
| MainHazards = potential [[carcinogen]]<ref name=PGCH/>
| LD50 = 45 mg/kg (oral, rabbit)<br/>49 mg/kg (oral, guinea pig)<br/>38 mg/kg (oral, mouse)<br/>65 mg/kg (oral, dog)<br/>38 mg/kg (oral, rat)<ref name=IDLH>{{IDLH|60571|Dieldrin}}</ref>
| FlashPt = noncombustible
| FlashPt_notes = <ref name=PGCH/>
| LC50 = 80 mg/m<sup>3</sup> (cat, 4 hr)<br/>13 mg/m<sup>3</sup> (rat, 4 hr)<ref name=IDLH/>
}} }}
'''Dieldrin''' is a [[chlorinated hydrocarbon]] originally produced in 1948 by J. Hyman & Co, Denver, as an [[insecticide]]. Dieldrin is closely related to [[aldrin]]. Aldrin reacts further to form dieldrin. Aldrin is not toxic to [[insect]]s; it is [[oxidation|oxidized]] in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the [[Diels-Alder reaction]] which is used to form aldrin from a mixture of norbornadiene and [[hexachlorocyclopentadiene]].

Dieldrin was developed as an alternative to [[DDT]] and has proved to be a highly effective insecticide. It was very widely used during the 1950s to early 1970s. [[Endrin]] is a [[stereoisomer]] of dieldrin.

However, it is an extremely [[persistent organic pollutant]]; it does not degrade easily. Furthermore, it tends to [[biomagnify]] as it is passed along the [[food chain]].  Long-term exposure has proven [[toxic|toxic]] to a very wide range of animals including humans. For this reason it is now banned in most of the world.

It has been linked to health problems such as [[Parkinson's disease]], [[breast cancer]], and immune, reproductive, and nervous system damage. It can also adversely affect testicular descent in the [[fetus]] if a pregnant woman is exposed to Dieldrin.

Dieldrin is listed in the [[Stockholm Convention on Persistent Organic Pollutants]].
== Synthesis ==
It can be formed from the synthesis of hexachloro-1,3-cyclopentadiene with [[norbornadiene]] in a [[Diels-Alder reaction]], followed by epoxidation of the norbornene ring.<ref name="Tedder">{{cite book |first=A. H. | last=Jubb |year=1975
  | title=Basic Organic Chemistry, Part 5 Industrial products |url=https://archive.org/details/trent_0116401244110 | publisher=Wiley
  | location=London | isbn=0-471-85014-4}}</ref>

[[Image:DieldrinSynthesis.png|thumbnail|left|480px|Synthesis of Dieldrin via a [[Diels-Alder reaction]]]]<div style="clear:left;"></div>
Dieldrin is named after [[Otto Paul Hermann Diels]], the co-inventor of the Diels-Alder reaction.
== References ==
<references/>

[[Category:Organochlorides]]
[[Category:Insecticides]]


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