Dichlorodiphenyldichloroethane

Dichlorodiphenyldichloroethane
Names


IUPAC names 1-chloro-4-[2,2-dichloro-1-(4- chlorophenyl)ethyl]benzene
Identifiers
CAS Number	72-54-8^Y
3D model (Jmol)	Interactive image
Abbreviations	DDD
Beilstein Reference	4-05-00-01884
ChEBI	CHEBI:27841^Y
ChEMBL	ChEMBL196590^Y
ChemSpider	6057^Y
ECHA InfoCard	100.000.712
EC Number	200-783-0
KEGG	C06636^Y
MeSH	DDD
PubChem	6294
InChI InChI=1S/C14H10Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8,13-14H^Y Key: AHJKRLASYNVKDZ-UHFFFAOYSA-N^Y InChI=1/C14H10Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8,13-14H Key: AHJKRLASYNVKDZ-UHFFFAOYAJ
SMILES Clc1ccc(cc1)C(c2ccc(Cl)cc2)C(Cl)Cl
Properties
Chemical formula	C₁₄H₁₀Cl₄
Molar mass	320.04
Appearance	Colorless and crystalline
Density	1.476 g/cm³
Melting point	109.5 °C (229.1 °F; 382.6 K)
Boiling point	350 °C (662 °F; 623 K)
Solubility in water	0.09 mg/L
log P	6.02 (octanol-water)
Vapor pressure	1.35×10⁻⁶ mm Hg
Henry's law constant (k_H)	6.6×10⁻⁶ atm ∙ m³/mol
Atmospheric OH rate constant	4.34×10⁻¹² cm³/molecule ∙ s
Related compounds
Related compounds	DDE, DDT, mitotane, perthane
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

Dichlorodiphenyldichloroethane (DDD) is an organochlorine insecticide that is slightly irritating to the skin.^[1] DDD is a metabolite of DDT.^[2] DDD is colorless and crystalline;^[3] it is closely related chemically and is similar in properties to DDT, but it is considered to be less toxic to animals than DDT.^[4] The molecular formula for DDD is (ClC₆H₄)₂CHCHCl₂ or C₁₄H₁₀Cl₄, whereas the formula for DDT is (ClC₆H₄)₂CHCCl₃ or C₁₄H₉Cl₅.

DDD is in the “Group B2” classification, meaning that it is a probable human carcinogen. This is based on an increased incidence of lung tumors in male and female mice, liver tumors in male mice, and thyroid tumors in male rats. Further basis is that DDD is so similar to and is a metabolite of DDT, another probable human carcinogen.^[2]

DDD is no longer registered for agricultural use in the United States, but the general population continues to be exposed to it due to its long persistence time. The primary source of exposure is oral ingestion of food.^[5]

1946 is the date of the earliest recorded use in English of the abbreviation “DDD” to stand for dichlorodiphenyldichloroethane, as far as could be determined.^[3]

Reductive dechlorination of DDT to form DDD

Mitotane

Interestingly enough, if one of the p-chlorines in DDD is switched to ortho-position, then we get a useful chemotherapeutic agent, mitotane. This is an example of a positional isomer.

Table of names

The following are synonyms for DDD:

Systematic Names	Superlist Names	Other Names
Benzene, 1,1'-(2,2- dichloroethylidene) bis(4-chloro- (9CI)	4,4'-DDD	1,1'-(2,2-Dichloroethylidene)bis (4-chlorobenzene)
Ethane, 1,1- dichloro-2,2-bis(p- chlorophenyl)-	Benzene, 1,1'-(2,2- dichloroethylidene)bis(4-chloro-	1,1-Bis(4-chlorophenyl)-2,2- dichloroethane
TDE	DDD	1,1-Bis(p-chlorophenyl)-2,2- dichloroethane
p,p'-TDE	DDD, p,p'-	1,1-Dichloor-2,2-bis(4-chloor fenyl)-ethaan (Dutch)
	Dichlorodiphenyldichloroethane	1,1-Dichlor-2,2-bis(4-chlor- phenyl)-aethan (German)
	RCRA waste number U060	1,1-Dichloro-2,2-bis(4- chlorophenyl)-ethane (French)
	TDE	1,1-Dichloro-2,2-bis(4- chlorophenyl)ethane
	Tetrachlorodiphenylethane	1,1-Dichloro-2,2-bis(p- chlorophenyl)ethane
	p,p'-TDE	1,1-Dichloro-2,2-bis (parachlorophenyl)ethane
		1,1-Dichloro-2,2-di(4- chlorophenyl)ethane
		1,1-Dicloro-2,2-bis(4-cloro-fenil)- etano (Italian)
		2,2-Bis(4-chlorophenyl)-1,1- dichloroethane
		2,2-Bis(p-chlorophenyl)-1,1- dichloroethane
		4,4' DDD
		4,4-DDD
		4,4'- Dichlorodiphenyldichloroethane
		4-05-00-01884 (Beilstein Handbook Reference)
		AI3-04225
		Benzene, 1,1'-(2,2- dichloroethylidene)bis[4-chloro-
		BRN 1914072
		CCRIS 573
		Caswell No. 307
		DDD analogue
		DDD in whole water sample
		Dichlorodiphenyl dichloroethane
		Dichlorodiphenyldichlorethane
		Dilene
		EINECS 200-783-0
		ENT 4,225
		EPA Pesticide Chemical Code 029101
		Ethane, 1,1-dichloro-2,2-bis(p- chlorophenyl)-
		HEPT
		HSDB 285
		ME-1700
		Me-700
		NCI-C00475
		NSC 8941
		OMS 1078
		para-para DDD
		para,para'-DDD
		para,para'- Dichlorodiphenyldichloroethane
		p,p-DDD
		p,p'-DDD
		p,p'-Dichlorodiphenyl-2,2-dichloroethylene
		p,p'-Dichlorodiphenyldichloroethane
		Rhothane
		Rhothane D-3
		Rothane
		Rothane WP-50

References

“Chemicals: Dichlorodiphenyldichloroethane.” The Comparative Toxicogenomics Database. MDI Biological Laboratory, 11 Apr. 2007 <http://ctd.mdibl.org/detail.go?type=chem&acc=D003632>.
“Data From SRC PhysProp Database.” SRC PhysProp Database. Syracuse Research Corporation. 11 Apr. 2007 <http://esc.syrres.com/interkow/webprop.exe?CAS=72-54-8>.
“DDD.” Hazardous Substances Data Bank. United States National Library of Medicine. 25 Apr. 2007 <http://toxmap.nlm.nih.gov/toxmap/main/chemPage.jsp?chem=4,4-DICHLORODIPHENYLDICHLOROETHANE then click “Env. Fate / Exposure”>.
“DDD—RN: 72-54-8.” ChemIDplus Lite Record. 9 Sept. 2004. United States National Library of Medicine Specialized Information Services. 11 Apr. 2007 <http://chem2.sis.nlm.nih.gov/chemidplus/direct.jsp?regno=72-54-8>.
Guralnik, David B., Editor in Chief. “DDD.” Webster’s New World Dictionary of the American Language. Second College Edition. New York, NY: Prentice Hall Press, 1986. ISBN 0-671-41809-2 (indexed), ISBN 0-671-41807-6 (plain edge), ISBN 0-671-41811-4 (pbk.), and ISBN 0-671-47035-3 (LeatherKraft).
Mish, Frederick C., Editor in Chief. “DDD.” Webster’s Ninth New Collegiate Dictionary. 9th ed. Springfield, MA: Merriam-Webster Inc., 1985. ISBN 0-87779-508-8, ISBN 0-87779-509-6 (indexed), and ISBN 0-87779-510-X (deluxe).
“p,p'-DDD.” Substance Registry System. 1 Feb. 2006. United States Environmental Protection Agency. 11 Apr. 2007 <http://iaspub.epa.gov/srs/srs_proc_qry.navigate?P_SUB_ID=4937>.
“p,p'-Dichlorodiphenyl dichloroethane (DDD) (CASRN 72-54-8).” Integrated Risk Information System. 25 Jan. 2007. United States Environmental Protection Agency. 23 Apr. 2007 <http://www.epa.gov/iris/subst/0347.htm>.

Notes

↑ Merck Index, 11th ed, p482
1 2 “p,p'-Dichlorodiphenyl dichloroethane (DDD) (CASRN 72-54-8).” Integrated Risk Information System. 25 Jan. 2007. United States Environmental Protection Agency. 23 Apr. 2007 <http://www.epa.gov/iris/subst/0347.htm>.
1 2 Mish, Frederick C., Editor in Chief. “DDD.” Webster’s Ninth New Collegiate Dictionary. 9th ed. Springfield, MA: Merriam-Webster Inc., 1985.
↑ Guralnik, David B., Editor in Chief. “DDD.” Webster’s New World Dictionary of the American Language. Second College Edition. New York, NY: Prentice Hall Press, 1986.
↑ “DDD.” Hazardous Substances Data Bank. United States National Library of Medicine. 25 Apr. 2007 <http://toxmap.nlm.nih.gov/toxmap/main/chemPage.jsp?chem=4,4-DICHLORODIPHENYLDICHLOROETHANE then click “Env. Fate / Exposure”>.

External links

TOXMAP Chemical Page for DDD
MSDS for rhothane (DDD) provided by the Physical and Theoretical Chemistry Laboratory of the University of Oxford

Pest control: Insecticides

Carbamates	Aldicarb Bendiocarb Carbaryl Carbofuran Ethienocarb Fenobucarb Oxamyl Methomyl Propoxur

Inorganic compounds	Aluminium phosphide Boric acid Chromated copper arsenate Copper(II) arsenate Copper(I) cyanide Diatomaceous earth Lead hydrogen arsenate Paris Green Scheele's Green

Insect growth regulators	Benzoylureas Diflubenzuron Flufenoxuron Hydroprene Lufenuron Methoprene Pyriproxyfen

Neonicotinoids	Acetamiprid Clothianidin Dinotefuran Imidacloprid Nitenpyram Nithiazine Thiacloprid Thiamethoxam

Organochlorides	Aldrin Beta-HCH Carbon tetrachloride Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon Toxaphene

Organophosphorus	Acephate Azamethiphos Azinphos-methyl Bensulide Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Demeton-S-methyl Diazinon Dicrotophos Diisopropyl fluorophosphate Dimethoate Dioxathion Disulfoton Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate Isoxathion Malathion Methamidophos Methidathion Mevinphos Monocrotophos Naled Omethoate Oxydemeton-methyl Parathion Parathion-methyl Phenthoate Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Quinalphos Temefos Tebupirimfos Terbufos Tetrachlorvinphos Tribufos Trichlorfon

Pyrethroids	Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin (I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin

Ryanoids	Chlorantraniliprole Cyantraniliprole Flubendiamide Ryanodine Ryanodol

Other chemicals	Afoxolaner Amitraz Azadirachtin Buprofezin Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner Pyridaben Pyriprole Ryanodine Sarolaner Sesamex Spinosad Sulfluramid Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone

Metabolites	Oxon Malaoxon Paraoxon TCPy

Biopesticides	Bacillus thuringiensis Baculovirus Beauveria bassiana Beauveria brongniartii Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paecilomyces fumosoroseus Paenibacillus popilliae Purpureocillium lilacinum

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