Flammable colorless liquid. Insoluble in water, miscible with benzene, toluene, carbon tetrachloride as well as ethanol, ether and ethyl acetate.
Propargyl Chloride is an intermediate in the pyrethroid propargyl pyrethroid, and is also used in the manufacture of pesticide soil fumigants.
Propargyl chloride, also known as 3-chloroprop-1-yne, is an organic compound that contains both a triple bond (alkyne) and a reactive chlorine atom. It is typically used as an intermediate in organic synthesis, particularly in the formation of a wide range of chemical products. When dissolved in dimethylformamide (DMF), a polar aprotic solvent, it is typically used in various chemical reactions, such as nucleophilic substitution or coupling reactions.
Melting point | <-50°C |
Boiling point | 58 °C(lit.) |
density | 1.03 g/mL at 25 °C(lit.) |
vapor pressure | 24.08-69.52kPa at 20-50℃ |
refractive index | n |
Fp | 7 °F |
storage temp. | 2-8°C |
solubility | benzene: miscible |
form | clear liquid |
color | Colorless to Red to Green |
Water Solubility | Not miscible or difficult to mix with water. |
Merck | 14,7810 |
BRN | 506005 |
Dielectric constant | 7.5599999999999996 |
Exposure limits | ACGIH: TWA 20 ppm OSHA: Ceiling 300 ppm; TWA 200 ppm NIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3) |
LogP | 1.3 at 25℃ |
CAS DataBase Reference | 624-65-7(CAS DataBase Reference) |
NIST Chemistry Reference | 1-Propyne, 3-chloro-(624-65-7) |
EPA Substance Registry System | 1-Propyne, 3-chloro- (624-65-7) |
Chemical Synthesis:
Propargyl chloride is widely used as a reactive intermediate in organic synthesis. It is used in the formation of various chemical compounds, including pharmaceuticals, agrochemicals, and polymeric materials. Due to the presence of the alkyne group, it is highly reactive and serves as a valuable building block for constructing more complex molecules.
Pharmaceutical Industry:
Propargyl chloride is used in the synthesis of various pharmaceutical compounds. The alkyne functionality is important in the development of drugs with specific biochemical activity. It can be used in the preparation of certain anti-cancer agents and other bioactive molecules.
Polymer Chemistry:
In polymer chemistry, propargyl chloride can be used in the preparation of crosslinked polymers or as a functional group in the modification of existing polymers. The alkyne group facilitates reactions with other chemical entities, enabling the creation of specialized polymer networks.
Synthesis of Specialty Chemicals:
This compound is used in the production of specialty chemicals, such as flame retardants, stabilizers, and surface-active agents. Its reactivity allows it to undergo several types of chemical transformations that are essential in the production of high-performance chemicals.
Coupling Reactions:
Propargyl chloride is frequently used in coupling reactions, where it reacts with various nucleophiles (such as amines, alcohols, or thiols) to form new carbon-carbon or carbon-heteroatom bonds. This makes it a useful reagent in the creation of complex organic compounds.
In chemical reactions, the propargyl group (–C≡C–CH2Cl) in propargyl chloride acts as a nucleophile, often undergoing nucleophilic substitution reactions where the chlorine atom is replaced by another group. This can lead to the formation of a variety of different products, depending on the nucleophile involved. The alkyne functionality, being electron-rich, also makes propargyl chloride reactive in coupling reactions and other transformations that require a triple bond.
Given its reactivity and the presence of both a chlorine atom and a triple bond, propargyl chloride should be handled with caution. Proper safety protocols are essential to minimize exposure and ensure safe usage.
Protective Gear:
Always wear gloves, goggles, and appropriate protective clothing when handling propargyl chloride. It can cause skin and eye irritation, and inhalation of vapors should be avoided.
Storage:
Store in a cool, dry place, away from direct sunlight and incompatible materials. It should be stored in tightly sealed containers to avoid contamination with moisture or air, which could lead to degradation.
Handling:
When using propargyl chloride in reactions, ensure good ventilation, as its vapors can be irritating. Keep containers closed and avoid open handling to minimize exposure to vapors.
Disposal:
Dispose of in accordance with local environmental and safety regulations. Waste should be handled as hazardous material, especially due to its chlorine content.
Health Hazards:
Inhalation: Inhalation of vapors may cause irritation to the respiratory system. Ensure that adequate ventilation is provided during handling.
Skin and Eye Contact: Propargyl chloride can cause irritation. In case of exposure, rinse immediately with plenty of water and seek medical attention if necessary.
Ingestion: Ingestion is highly toxic and should be avoided. Seek medical attention immediately in case of ingestion.
Propargyl chloride (85% in DMF) is a versatile and highly reactive compound used in a range of chemical syntheses, including pharmaceutical, polymer, and specialty chemical production. Its utility stems from its ability to participate in nucleophilic substitution and coupling reactions, thanks to its alkyne group and reactive chlorine atom. As with all chemicals, handling propargyl chloride requires caution, with proper protective equipment and disposal protocols to minimize risk.
1. What is Propargyl Chloride used for?
Propargyl chloride is used primarily as an intermediate in organic synthesis, including the production of pharmaceuticals, polymers, and specialty chemicals. It is also used in coupling reactions.
2. What is the solvent for 85% Propargyl Chloride?
The solvent for 85% Propargyl Chloride is Dimethylformamide (DMF), a polar aprotic solvent that aids in dissolving the compound and facilitating chemical reactions.
3. How should Propargyl Chloride be stored?
Store in a cool, dry place, away from moisture and incompatible materials, in tightly sealed containers. Avoid exposure to sunlight and high temperatures.
4. What safety precautions should be taken when handling Propargyl Chloride?
Wear protective gloves, goggles, and suitable clothing. Ensure good ventilation when working with the compound. Avoid inhaling vapors and contact with skin and eyes.
5. Is Propargyl Chloride hazardous?
Yes, Propargyl Chloride is hazardous. It can cause skin and eye irritation and is toxic if ingested or inhaled. Always follow proper safety guidelines to minimize exposure.
6. Can Propargyl Chloride be used in food products?
No, Propargyl Chloride is not used in food products. It is primarily an industrial chemical used in the synthesis of various organic compounds.
7. Can Propargyl Chloride react with water?
Propargyl Chloride is sensitive to moisture and can degrade when exposed to water. It should be handled and stored carefully to avoid contact with water.