Dichlorodiphenyldichloroethane

Dichlorodiphenyldichloroethane
IUPAC name 1-chloro-4-[2,2-dichloro-1-(4- chlorophenyl)ethyl]benzene
Identifiers
Abbreviations	DDD
CAS number	72-54-8 Y
PubChem	6294
ChemSpider	6057 Y
EC number	200-783-0
KEGG	C06636 Y
MeSH	DDD
ChEBI	CHEBI:27841 Y
ChEMBL	CHEMBL196590 Y
Beilstein Reference	4-05-00-01884
Jmol-3D images	Image 1
SMILES Clc1ccc(cc1)C(c2ccc(Cl)cc2)C(Cl)Cl
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
Properties
Molecular formula	C14H10Cl4
Molar mass	320.04
Appearance	Colorless and crystalline
Melting point	109.5 °C (229.1 °F (109.5 °C))
Boiling point	350 °C (662 °F (350 °C))
Solubility in water	0.09 mg/L
log P	6.02 (octanol-water)
Vapor pressure	1.35×10−6 mm Hg
kH	6.6×10−6 atm ∙ m³/mol
Atmospheric OH rate constant	4.34×10−12 cm³/molecule ∙ s
Pharmacology
Elimination half-life	4 days in air; 160 days in anaerobic soil; when in water (hydrolysis), depends on various factors (one or more decades in rivers and lakes, 190 years at 27 °C and pH 3–5)[1]
Related compounds
Related compounds	DDE, DDT, mitotane, perthane
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Dichlorodiphenyldichloroethane (DDD) is an organochlorine insecticide that is slightly irritating to the skin.^[2] DDD is a metabolite of DDT.^[3] DDD is colorless and crystalline^[4]; it is closely related chemically and is similar in properties to DDT, but it is considered to be less toxic to animals than is DDT.^[5] 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.^[3]

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.^[1]

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.^[4]

Reductive dechlorination of DDT to form DDD

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. Mount Desert Island 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

1. ^ ^{a b} “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”>.
2. ^ Merck Index, 11th ed, p482
3. ^ ^{a b} “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>.
4. ^ ^{a b} Mish, Frederick C., Editor in Chief. “DDD.” Webster’s Ninth New Collegiate Dictionary. 9th ed. Springfield, MA: Merriam-Webster Inc., 1985.
5. ^ 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.

External links

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