Dichlorodiphenyldichloroethane

Last updated
Dichlorodiphenyldichloroethane
P,p'-dichlorodiphenyldichloroethane.svg
Dichlorodiphenyldichloroethane-from-xtal-3D-bs-17.png
Names
IUPAC name
1-chloro-4-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene
Preferred IUPAC name
1,1′-(2,2-dichloroethane-1,1-diyl)bis(4-chlorobenzene)
Identifiers
3D model (JSmol)
AbbreviationsDDD
4-05-00-01884
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.712 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-783-0
KEGG
MeSH DDD
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: AHJKRLASYNVKDZ-UHFFFAOYSA-N Yes check.svgY
  • 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
  • Clc1ccc(cc1)C(c2ccc(Cl)cc2)C(Cl)Cl
Properties
C14H10Cl4
Molar mass 320.03 g·mol−1
AppearanceColorless 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)
0.09 mg/L
log P 6.02 (octanol-water)
Vapor pressure 1.35×10−6 mm Hg
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).
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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.

Contents

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. A further basis is that DDD is 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 Reductive dechlorination DDT DDD.svg
Reductive dechlorination of DDT to form DDD

Mitotane

Mitotane.svg

If one of the p-chlorines in DDD is switched to ortho-position, the result is the chemotherapeutic agent mitotane. This is an example of a positional isomer.

Table of names

The following are synonyms for DDD:

Systematic Names Superlist NamesOther Names
Benzene, 1,1'-(2,2-
dichloroethylidene)
bis(4-chloro- (9CI)		4,4'-DDD1,1'-(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
TDEDDD1,1-Bis(p-chlorophenyl)-2,2-
dichloroethane
p,p'-TDEDDD, p,p'-1,1-Dichloor-2,2-bis(4-chloor fenyl)-ethaan (Dutch)
Dichlorodiphenyldichloroethane1,1-Dichlor-2,2-bis(4-chlor-
phenyl)-aethan (German)
RCRA waste number U0601,1-Dichloro-2,2-bis(4-
chlorophenyl)-ethane (French)
TDE1,1-Dichloro-2,2-bis(4-
chlorophenyl)ethane
Tetrachlorodiphenylethane1,1-Dichloro-2,2-bis(p-
chlorophenyl)ethane
p,p'-TDE1,1-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

Notes

  1. ↑ Merck Index, 11th ed, p482
  2. 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 <>.
  3. 1 2 Mish, Frederick C., Editor in Chief. “DDD.” Webster’s Ninth New Collegiate Dictionary. 9th ed. Springfield, MA: Merriam-Webster Inc., 1985.
  4. ↑ 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.
  5. ↑ “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 Archived 2012-02-07 at the Wayback Machine then click “Env. Fate / Exposure”>.
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