3-Chloropropyne
[CAS# 624-65-7]

Identification

• Classification: Chemical pesticide >> Insecticide intermediate
• Name: 3-Chloropropyne
• Synonyms: 3-Chloro-1-propyne; Propargyl chloride
• Molecular Formula: C₃H₃Cl
• Molecular Weight: 74.51
• CAS Registry Number: 624-65-7
• EC Number: 210-856-9
• SMILES: C#CCCl

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*, Density
• Index of Refraction: 1.423, Calc.^*
• Boiling Point: 57.0±0.0 °C (760 mmHg), Calc.^*, 58 °C (Expl.)
• Flash Point: 18.9±0.0 °C, Calc.^*, -15 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS06;GHS07 Danger
• Risk Statements: H225-H301-H311-H314-H318-H330-H331-H335-H412
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P284-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P319-P320-P321-P330-P361+P364-P363-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Flammable liquids	Flam. Liq.	2	H225
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331

• Transport Information: UN 3286

Discovery and Applications

3-Chloropropyne, also known as 3-chloro-1-propyne, is a chemical compound that belongs to the class of alkynes. It consists of a three-carbon chain with a triple bond between the first and second carbon atoms and a chlorine atom attached to the third carbon. The compound was first synthesized in the early 20th century during the investigation of alkynes and their reactivity. Over time, 3-chloropropyne has been recognized for its utility in organic synthesis, particularly in the creation of specialized chemical intermediates and in the development of various materials.

The discovery of 3-chloropropyne is tied to the broader exploration of alkyne chemistry, which has provided a wide range of important compounds with useful chemical reactivity. Alkynes, characterized by a carbon-carbon triple bond, are highly reactive and participate in a variety of chemical reactions that make them valuable in organic synthesis. The introduction of a chlorine atom in 3-chloropropyne enhances its reactivity, making it a useful intermediate for the production of other chemicals. The compound is typically synthesized through the chlorination of propyne, a simple alkyne, under controlled conditions that allow the chlorine atom to be selectively added to the third carbon of the molecule.

One of the primary applications of 3-chloropropyne is in organic synthesis, where it serves as a valuable building block for the creation of more complex chemical structures. The compound is often used as a precursor in the synthesis of various pharmaceuticals, agrochemicals, and specialty chemicals. For example, it can undergo nucleophilic substitution reactions, where the chlorine atom is replaced by other functional groups such as alkyl, aryl, or halide substituents. These reactions allow for the creation of a wide range of derivatives with different functional properties.

In addition to its use in the synthesis of organic compounds, 3-chloropropyne has applications in the development of materials and coatings. The compound is often incorporated into the production of specialty polymers, particularly those that require specific functional groups or reactivity. 3-chloropropyne can be polymerized or copolymerized with other monomers to create materials with enhanced properties, such as increased strength, chemical resistance, or flexibility. These materials are useful in a wide range of industries, including coatings, adhesives, and sealants.

3-chloropropyne is also used in the production of fine chemicals, where its unique reactivity allows for the creation of complex molecular structures. For example, it can be used as a precursor in the synthesis of chlorinated aromatic compounds, which are important in the manufacture of dyes, pigments, and other colorants. The chlorination of the propynyl group in 3-chloropropyne opens up possibilities for a range of reactions that are essential for the development of these products. As a result, 3-chloropropyne is an important intermediate in the chemical industry, particularly in the production of specialty chemicals for various commercial applications.

Furthermore, the compound has been studied for its potential role in the development of novel materials for electronic and optoelectronic devices. Due to its ability to undergo reactions that introduce functional groups with specific electronic properties, 3-chloropropyne can be used in the design of organic semiconductors, which are critical components in devices such as organic light-emitting diodes (OLEDs) and organic solar cells. Its incorporation into these materials can help improve their efficiency and stability, making it a promising compound for the future of flexible and organic electronics.

In conclusion, 3-chloropropyne is a versatile and reactive chemical compound with a wide range of applications in organic synthesis, materials science, and the development of specialty chemicals. Its unique structure and reactivity make it a valuable building block for the creation of complex chemical products and materials, as well as a precursor for the manufacture of a variety of commercial products. As research into its applications continues, 3-chloropropyne is likely to remain an important compound in the field of industrial chemistry.

References

2018. Synthesis and characterization of conjugated and nanostructured poly(propargyl alcohol) polymers. Journal of Polymer Research, 25(4).
DOI: 10.1007/s10965-018-1496-4

2019. Synthesis of block copolymer including polyepichlorohydrin and polyethylene glycol by “click” chemistry: evaluation of primary parameters of copolymerization. Polymer Bulletin, 77(10).
DOI: 10.1007/s00289-019-02989-4

2023. Synthesis and characterization of poly(epichlorohydrin-g-4-vinylbenzyl-g-methyl methacrylate) graft copolymer by combination of ROP, RAFT, and ATRP Technics. Journal of Polymer Research, 30(7).
DOI: 10.1007/s10965-023-03598-6