Dichlorodiphenyldichloroethane

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Dichlorodiphenyldichloroethane
P,p'-dichlorodiphenyldichloroethane.svg
Identifiers
Abbreviations DDD
CAS number 72-54-8 YesY
PubChem 6294
ChemSpider 6057 YesY
EC number 200-783-0
KEGG C06636 YesY
MeSH DDD
ChEBI CHEBI:27841 YesY
ChEMBL CHEMBL196590 YesY
Beilstein Reference 4-05-00-01884
Jmol-3D images Image 1
Properties
Molecular formula C14H10Cl4
Molar mass 320.04
Appearance Colorless and crystalline
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
kH 6.6×10−6 atm ∙ m³/mol
Atmospheric OH rate constant 4.34×10−12 cm³/molecules
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
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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

Mitotane[edit]

Mitotane.svg

Interestingly enough, if one of the p-chlorine's 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[edit]

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[edit]

Notes[edit]

  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[edit]