Allyl chloride is a clear, flammable liquid with a pungent odor. It is used in the production of various organic compounds and as a solvent. It can be harmful to humans if inhaled or ingested.
| IUPAC name | 3-chloroprop-1-ene |
| Molecular formula | C3H5Cl |
| CAS number | 107-05-1 |
| Synonyms | 2-Propenyl chloride, 3-chloropropene, Chloropropene, Allychloride, 3-chloro-1-propene, 1-chloro-2-propene |
| InChI | InChI=1S/C3H5Cl/c1-2-3-4/h2H,1,3H2 |
Allyl Chloride Properties
Allyl Chloride Formula
The chemical formula of allyl chloride is C3H5Cl. It is a clear and colorless liquid with a pungent odor. The structure of allyl chloride consists of a propene molecule with a chlorine atom attached to the second carbon atom. It is an important intermediate in the production of various organic compounds, such as epoxides, allylamines, and allylic alcohols.
Allyl Chloride Molar Mass
The molar mass of 3-chloropropene is 76.53 g/mol. This is calculated by adding the atomic weights of carbon, hydrogen, and chlorine, which are 12.01 g/mol, 1.01 g/mol, and 35.45 g/mol, respectively. The molar mass is an important property of a chemical compound as it is used to calculate the amount of substance in a given mass.
Allyl Chloride Boiling Point
The boiling point of 3-chloropropene is 46.05 °C (114.9 °F). This is relatively low compared to other organic compounds, which makes 3-chloropropene a volatile substance. The low boiling point also makes 3-chloropropene useful in industrial processes as it can be easily evaporated and condensed to purify it.
Allyl Chloride Melting Point
The melting point of 3-chloropropene is -136 °C (-213 °F). This is a very low temperature and means that 3-chloropropene exists as a liquid at room temperature. However, when 3-chloropropene is cooled to very low temperatures, it can solidify into a white crystalline form.
Allyl Chloride Density g/mL
The density of 3-chloropropene is 0.950 g/mL. This means that 3-chloropropene is denser than water, which has a density of 1 g/mL. The high density of 3-chloropropene makes it useful in separating it from other substances with lower densities, such as water.
Allyl Chloride Molecular Weight
The molecular weight of 3-chloropropene is 76.53 g/mol. This value is calculated by adding the atomic weights of all the atoms in the molecule. The molecular weight is important in determining the physical and chemical properties of a compound.
Allyl Chloride Structure
The structure of 3-chloropropene consists of a propene molecule with a chlorine atom attached to the second carbon atom. This forms a vinyl group, which is a functional group in organic chemistry. The vinyl group is responsible for the reactivity of 3-chloropropene in various chemical reactions.
Allyl Chloride Solubility
3-chloropropene is soluble in many organic solvents, such as ether and benzene, but is insoluble in water. The solubility of 3-chloropropene in different solvents is due to its polar nature. The polarity of 3-chloropropene is determined by the electronegativity difference between the carbon-hydrogen bond and the carbon-chlorine bond.
| Appearance | Clear colorless liquid |
| Specific gravity | 0.950 g/mL |
| Color | Colorless |
| Odor | Pungent |
| Molar mass | 76.53 g/mol |
| Density | 0.950 g/mL |
| Melting point | -136 °C (-213 °F) |
| Boiling point | 46.05 °C (114.9 °F) |
| Flash point | -13 °C (9 °F) |
| Water solubility | < 1 g/L |
| Solubility | Soluble in organic solvents |
| Vapour pressure | 21.5 kPa at 20°C |
| Vapour density | 2.64 (air = 1) |
| pKa | 9.18 |
| pH | Not applicable (pH is only defined for aqueous solutions) |
Allyl Chloride Safety and Hazards
3-chloropropene is a highly toxic and corrosive substance. It can cause severe skin burns and eye damage upon contact and can be harmful if inhaled or swallowed. It is also highly flammable and can react violently with certain compounds. Proper safety precautions should be taken when working with 3-chloropropene, including wearing protective clothing, gloves, and eye protection. It should be stored in a cool, dry, and well-ventilated area away from heat and ignition sources. In case of exposure or ingestion, medical attention should be sought immediately. It is important to follow proper safety protocols to prevent accidents and injuries when handling 3-chloropropene.
| Hazard symbols | T, C |
| Safety description | Highly flammable, toxic, and corrosive. Causes severe skin burns and eye damage. Harmful if inhaled or swallowed. |
| UN IDs | UN 1100 |
| HS code | 2903.39.90 |
| Hazard class | Class 3 (Flammable liquids), Class 6.1 (Toxic substances), Class 8 (Corrosive substances) |
| Packing group | II |
| Toxicity | LD50 = 250 mg/kg (oral, rat); LC50 = 1220 ppm (inhalation, rat, 4h) |
Allyl Chloride Synthesis Methods
Several methods can synthesize 3-chloropropene.
One of the most common methods is the addition of hydrogen chloride gas to allyl alcohol in the presence of a catalyst. Another method involves the reaction of propylene with chlorine gas in the presence of a catalyst to form 3-chloropropene.
To prepare 3-chloropropene, one can react allyl alcohol with thionyl chloride or phosphorus trichloride. This reaction involves converting the alcohol to its corresponding chloride through a nucleophilic substitution reaction.
A third method for preparing 3-chloropropene involves the reaction of allyl bromide with sodium chloride in the presence of copper powder. Chemists often use this method when they have ready access to allyl bromide but do not have 3-chloropropene.
Another method for synthesizing 3-chloropropene involves the reaction of allyl alcohol with hydrogen chloride gas in the presence of a dehydrating agent such as zinc chloride. Chemists often use this method to prepare 3-chloropropene with high yield and purity.
Allyl Chloride Uses
3-chloropropene has several important uses in various industries due to its unique properties:
- Production of allyl compounds: 3-chloropropene serves as a precursor to various allyl compounds such as allyl alcohol, allyl amine, and allyl esters. The production of pharmaceuticals, fragrances, and flavors commonly involves the use of allyl compounds.
- Polymer production: Manufacturers utilize 3-chloropropene as a monomer to produce various polymers, such as poly3-chloropropene and allyl diglycol carbonate.
- Solvent: Used as a solvent for various organic compounds due to its low boiling point and high polarity.
- Pesticide: Used as a fumigant and soil sterilant in agriculture to control pests and weeds.
- Dye and pigment production: Used in the production of dyes and pigments for textile and paint industries.
- Oil and gas industry: Also used in the oil and gas industry as a corrosion inhibitor, lubricant, and drilling fluid additive.
Questions:
Q: Why does allyl chloride undergo SN1 reactions even though it is a 1° halide?
A: 3-chloropropene undergoes SN1 reactions due to the stability of the intermediate carbocation, which is resonance-stabilized by the allyl group.
Q: What happens to allyl chloride in an SN2 reaction?
A: In an SN2 reaction, the nucleophile attacks the allylic carbon from the backside, leading to inversion of stereochemistry and formation of the corresponding allylic alcohol or amine.
Q: Is allyl chloride primary, secondary, or tertiary?
A: 3-chloropropene is a primary halide.
Q: Which of the following reactions occurs faster, AcO- + 3-chloropropene or MeO- + 3-chloropropene? A: MeO- + 3-chloropropene occurs faster than AcO- + 3-chloropropene due to steric hindrance caused by the larger acetyl group in the latter.
Q: Is allyl chloride a primary vinyl halide?
A: Yes, 3-chloropropene is a primary vinyl halide.
Q: How can epichlorohydrin be made from allyl chloride?
A: Epichlorohydrin can be made from 3-chloropropene through an epoxidation reaction using a mixture of sodium hypochlorite and hydrochloric acid.