Dichlorodiphenyldichloroethane

Dichlorodiphenyldichloroethane
Skeletal formula of DDD
Ball-and-stick model of the DDD molecule
Names
IUPAC names
1-chloro-4-[2,2-dichloro-1-(4-
chlorophenyl)ethyl]benzene
Identifiers
72-54-8 YesY
Abbreviations DDD
4-05-00-01884
ChEBI CHEBI:27841 YesY
ChEMBL ChEMBL196590 YesY
ChemSpider 6057 YesY
EC Number 200-783-0
Jmol interactive 3D Image
KEGG C06636 YesY
MeSH DDD
PubChem 6294
Properties
C14H10Cl4
Molar mass 320.04
Appearance Colorless 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/molecules
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).
YesY verify (what is YesYN ?)
Infobox references

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.

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.[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

Mitotane

Interestingly enough, if one of the p-chlorines 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

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. 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 <http://www.epa.gov/iris/subst/0347.htm>.
  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 then click “Env. Fate / Exposure”>.

External links

This article is issued from Wikipedia - version of the Wednesday, March 16, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.