1,3-Dichloropropene
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| 1,3-Dichloropropene | |
|---|---|
| Image:Trans-1,3-Dichloropropene.svg | |
| Image:Cis-1,3-Dichloropropene.svg | |
| 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 | |
| PubChem | |
| EINECS number | |
| KEGG | |
| MeSH | |
| ChEBI | |
| 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 |
|
| 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.[citation needed]
A few workers who had skin contact with pesticides containing DCP developed blisters and an allergic reaction on their skin.[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]
| 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]
References
- ATSDR ToxFAQs™: Dichloropropenes
- ATSDR ToxFAQs™: Dichloropropenes
- USGS Pesticide National Synthesis Project - Crop & Compound
- ATSDR Toxicological Profile (9.2 MB)
Further reading
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
