1,3-Dichloropropene
[CAS# 542-75-6]

Identification

• Classification: Chemical pesticide >> Herbicide >> Carbamate herbicide
• Name: 1,3-Dichloropropene
• Synonyms: 1,3-Dichloro-2-propene; 1,3-Dichloropropylene
• Molecular Formula: C₃H₄Cl₂
• Molecular Weight: 110.97
• CAS Registry Number: 542-75-6
• EC Number: 208-826-5
• SMILES: C(C=CCl)Cl

Properties

• Density: 1.22
• Melting point: -60 ºC
• Boiling point: 108 ºC
• Refractive index: 1.469-1.475
• Flash point: 27 ºC
• Water solubility: <0.01 g/100 mL at 16.5 ºC

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS08;GHS09 Danger
• Hazard Statements: H226-H311-H301-H332-H304-H335-H315-H319-H317-H400-H410
• Safety Description: S36/37;S45;S60;S61

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Flammable liquids	Flam. Liq.	3	H226
Skin sensitization	Skin Sens.	1	H317
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H311
Aspiration hazard	Asp. Tox.	1	H304
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H411
Carcinogenicity	Carc.	2	H351
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	2	H371
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

• Transport Information: UN 2047;UN 1992

Discovory and Applicatios

1,3-Dichloropropene is a colorless, flammable liquid with the molecular formula C3H4Cl2. It belongs to the class of organic compounds known as chloropropenes, which are characterized by the presence of double bonds and chlorine substituents. The compound is primarily recognized for its application as a soil fumigant and as a precursor in the synthesis of other chemicals.

The discovery of 1,3-dichloropropene dates back to the early 20th century when chemists were investigating various chlorinated hydrocarbons for their potential industrial uses. The compound was first synthesized through the chlorination of propylene, a byproduct of petroleum refining. Researchers quickly recognized its potential as an effective pest control agent, leading to its development as a widely used agricultural fumigant.

1,3-Dichloropropene's primary application is in agriculture, where it is employed as a soil fumigant to control nematodes, weeds, and various soil-borne pathogens. Its ability to penetrate the soil effectively makes it a valuable tool for growers seeking to protect crops from harmful pests and diseases. The compound is typically applied before planting, allowing it to act on the soil and eliminate unwanted organisms. Its use has been particularly important in the cultivation of high-value crops such as tomatoes, potatoes, and strawberries.

In addition to its agricultural applications, 1,3-dichloropropene is utilized in the production of various chemical intermediates. It can undergo reactions such as hydrolysis and alkylation, resulting in the formation of a range of derivatives, including chlorinated alkenes and other valuable organic compounds. These derivatives find applications in the manufacturing of plastics, solvents, and other specialty chemicals, further enhancing the compound's industrial significance.

Despite its usefulness, the use of 1,3-dichloropropene has raised environmental and health concerns. The compound is classified as a potential human carcinogen and poses risks to non-target organisms, including beneficial soil microbes and insects. Consequently, regulatory agencies have established guidelines for its use, limiting application rates and requiring protective measures for workers handling the substance. Researchers continue to explore alternatives to 1,3-dichloropropene, seeking to develop safer and more environmentally friendly pest control solutions.

Efforts to mitigate the risks associated with 1,3-dichloropropene have led to increased interest in integrated pest management (IPM) practices that combine chemical, biological, and cultural controls. By using 1,3-dichloropropene judiciously and in conjunction with other strategies, farmers can minimize its environmental impact while maintaining effective pest control.

In conclusion, 1,3-dichloropropene is a significant chemical compound with valuable applications in agriculture and chemical synthesis. Its role as a soil fumigant has been crucial in protecting crops from pests and diseases, contributing to agricultural productivity. However, the compound's environmental and health concerns necessitate careful management and ongoing research into safer alternatives. As agricultural practices evolve, 1,3-dichloropropene may continue to play a role in pest management while addressing the challenges of sustainability and safety.