Dichlorodiphenyldichloroethane (DDD) is an organochlorine insecticide that is slightly irritating to the skin.Merck Index, 11th ed, p482 DDD is a metabolite of DDT.“p,p'-Dichlorodiphenyl dichloroethane (DDD) (CASRN 72-54-8).” Integrated Risk Information System. 25 Jan. 2007. United States Environmental Protection Agency. 23 Apr. 2007 <>. DDD is colorless and crystalline;Mish, Frederick C., Editor in Chief. “DDD.” Webster’s Ninth New Collegiate Dictionary. 9th ed. Springfield, MA: Merriam-Webster Inc., 1985. it is closely related chemically and is similar in properties to DDT, but it is considered to be less toxic to animals than DDT.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. 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. A further basis is that DDD is similar to and is a metabolite of DDT, another probable human carcinogen.
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.“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”>.
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.
Mitotane
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 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 <https://web.archive.org/web/20070927230912/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 <https://web.archive.org/web/20120207033729/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 <https://web.archive.org/web/20110717080344/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. (indexed), (plain edge), (pbk.), and (LeatherKraft). Mish, Frederick C., Editor in Chief. “DDD.” Webster’s Ninth New Collegiate Dictionary. 9th ed. Springfield, MA: Merriam-Webster Inc., 1985. , (indexed), and (deluxe). “p,p'-DDD.” Substance Registry System. 1 Feb. 2006. United States Environmental Protection Agency. 11 Apr. 2007 <https://web.archive.org/web/20061008163205/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 <>.
Notes
External links TOXMAP Chemical Page for DDD MSDS for rhothane (DDD) provided by the Physical and Theoretical Chemistry Laboratory of the University of Oxford