Dichlorodiphenyldichloroethane

Dichlorodiphenyldichloroethane
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 (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/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
 YesY (verify) (what is: YesY/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

Contents

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

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


Wikimedia Foundation. 2010.

Look at other dictionaries:

  • Dichlorodiphényldichloroéthane — Général Nom IUPAC 1,1 (2,2 dichloroéthane 1,1 diyl)bis(4 chlorobenzène) …   Wikipédia en Français

  • dichlorodiphenyldichloroethane — noun An organochlorine insecticide that is a metabolite of DDT. Syn: DDD See Also: dichlorodiphenyltrichloroethane …   Wiktionary

  • DDT — For other uses, see DDT (disambiguation). DDT …   Wikipedia

  • DDD — can refer to, among others: Contents 1 Science and humanities 2 Industry and economy 3 Computers and Technology 4 Entertainment and popular culture …   Wikipedia

  • Mitotane — Systematic (IUPAC) name (RS) 1 chloro 2 [2,2 dichloro 1 (4 chlorophenyl) ethyl] benzene Clinical data AHFS/Drugs.com …   Wikipedia

  • 50-29-3 — Dichlorodiphényltrichloroéthane « DDT » redirige ici. Pour les autres significations, voir DDT (homonymie) …   Wikipédia en Français

  • C14H9Cl5 — Dichlorodiphényltrichloroéthane « DDT » redirige ici. Pour les autres significations, voir DDT (homonymie) …   Wikipédia en Français

  • DDD — Cette page d’homonymie répertorie les différents sujets et articles partageant un même nom.   Sigles d’une seule lettre   Sigles de deux lettres > Sigles de trois lettres   Sigles de quatre lettres …   Wikipédia en Français

  • DDT — Dichlorodiphényltrichloroéthane « DDT » redirige ici. Pour les autres significations, voir DDT (homonymie) …   Wikipédia en Français

  • Dichlorodiphenyltrichloroethane — Dichlorodiphényltrichloroéthane « DDT » redirige ici. Pour les autres significations, voir DDT (homonymie) …   Wikipédia en Français


Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”

We are using cookies for the best presentation of our site. Continuing to use this site, you agree with this.