1,3-Dichloropropene

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1,3-Dichloropropene
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IUPAC name 1,3-dichloroprop-1-ene
Systematic name 1-Propene, 1,3-dichloro-, (1E)-
Other names Dorlone, Nematox, Telone, Nemex, trans-Telone, Dorlone II, Telone C, Telone II, cis-Dichloropropene, Di-Trapex CP, Telone II-B, Vorlex 201, dichloro-1,3-propene, 1,3-dichloro-1-propene, 1,3-dichloro-2-propene, alpha-chloroallylchloride, chloroallylchloride, gamma-chloroallylchloride, chloroallyl chloride, chloroorpropenyl chloride, 3-dichloropropylene, 3-D, DCP
Identifiers
CAS number 542-75-6
PubChem 24726
EINECS number 208-826-5
KEGG C06609
MeSH 1,3-dichloro-1-propene
ChEBI 18918
RTECS number UC8310000
SMILES C(C=CCl)Cl
InChI InChI=1/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1
Properties
Molecular formula C3H4Cl2
Molar mass 110.97 g/mol
Appearance Colorless to straw-colored liquid, sweet chloroform-like odor
Density 1.217 g/mL (cis); 1.224 g/mL (trans)
Melting point

-84.5 °C

Boiling point

104 °C (cis); 112 °C (trans)

Solubility in water 2.18 g/L (cis) @ 25 °C; 2.32 g/L (trans) @ 25 °C
log P 1.82
Vapor pressure 34.4 mm Hg @ 25 °C (cis); 23.0 mm Hg @ 25 °C (trans)
Hazards
EU classification T,N
EU Index 208-826-5
NFPA 704

NFPA 704.svg

3
2
0
 
R-phrases 10-20/21-25-36/37/38-43-50/53
S-phrases (1/2-)-36/37-45-60-61
Flash point 28 °C
Autoignition
temperature
> 500 °C
Explosive limits 5.3% - 14.5% (80 °C)
U.S. Permissible
exposure limit (PEL)
1
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Overview

1,3-Dichloropropene is a colorless liquid with a sweet smell. It dissolves in water and evaporates easily. It is used mainly in farming as a pesticide. It exists as a mixture of the geometric isomers cis-1,3-dichloropropene and trans-1,3-dichloropropene.

Effects

1,3-Dichloropropene (DCP) causes irritation at the point of contact. Inhalation can cause nausea, vomiting, irritation of the skin, eyes, and throat; breathing difficulties, headache, and fatigue. These effects generally occurr at exposure levels that are much higher than the background levels found in air or water. Rats and mice that inhaled DCP repeatedly for about 2 weeks had damage to the lining of the nose, and mice had damage to the lung.

A man who accidentally ingested DCP died with severe damage to his stomach and surrounding organs, but little else is known about the effects of ingesting these substances in humans. Animal studies have reported damage to the stomach lining, lung congestion, difficulty walking, and effects on the liver and kidneys from ingesting high levels of DCP.Template:Fix/category[citation needed]

A few workers who had skin contact with pesticides containing DCP developed blisters and an allergic reaction on their skin.Template:Fix/category[citation needed]

It is not known whether DCP can cause birth defects in humans. Pregnant rats that inhaled 1,3-dichloropropene gave birth to fewer pups or pups with lower body weight. This occurred at exposures high enough to be toxic to the mothers.[1]

DCP is testable via blood and urine tests, although it is only detectable in the body for 1-2 after exposure. Exposure level estimates are possible with a blood sample.

Carcinogenicity

Evidence for the carcinogenicity of 1,3-dichloropropene in humans is inadequate, but results from several cancer bioassays provide adequate evidence of carcinogenicity in animals. The Department of Health and Human Services (DHHS) has determined that 1,3-dichloropropene may reasonably be anticipated to be a carcinogen. The International Agency for Research on Cancer (IARC) has determined that 1,3-dichloropropene is possibly carcinogenic to humans. The EPA has classified 1,3-dichloropropene as a probable human carcinogen.[2]

Use

1,3-Dichloropropene is used as a pesticide in the following crops: [3]

1,3-Dichloropropene Use in Crops
Crop Pounds (lb) Primary Pesticide?
Tobacco 12,114,887 Yes
Potatoes 12,044,736 Yes
Sugar Beets 5,799,613 Yes
Cotton 3,735,543 Yes
Peanuts 3,463,003 Yes
Sweet Potatoes 1,210,872 Yes
Onions 674,183 Yes
Carrots 531,752 Yes
Watermelons 133,801 No
Cantaloups 121,395 No
Cucumbers 76,735 No
Strawberries 71,753 No
Sweet Peppers 28,247 No
Melons 12,471 No
Blueberries 3,090 No
Asparagus 1,105 No

Contamination

The ATSDR has extensive contamination information available.[4]

File:Frequency of npl sites with DCP contam.png
Frequency of NPL Sites with 1,3-Dichloropropene Contamination

References

Further reading



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