Acetyl chloride or C2H3ClO is a colorless, fuming liquid with a pungent odor. It is primarily used as a reagent in organic synthesis and as an acetylating agent in the production of pharmaceuticals and dyes.
| UPAC Name | Acetyl chloride |
| Molecular Formula | C2H3ClO |
| CAS number | 75-36-5 |
| Synonyms | Ethanoyl chloride, acetic acid chloride, acetic chloride, chloroacetyl chloride, AcCl |
| InChI | InChI=1S/C2H3ClO/c1-2(3)4/h1H3 |
Acetyl Chloride Properties
Acetyl Chloride Molar Mass
Acetyl chloride, with the chemical formula C2H3ClO, has a molar mass of approximately 78.50 g/mol. This is calculated by adding the atomic masses of each atom in the molecule, which are carbon (12.01 g/mol), hydrogen (1.01 g/mol), chlorine (35.45 g/mol), and oxygen (16.00 g/mol). The molar mass of acetyl chloride is important in stoichiometric calculations for determining the amount of reactants and products in chemical reactions.
Acetyl Chloride Boiling Point
The boiling point of acetyl chloride is 51.5 °C (124.7 °F) at standard atmospheric pressure. This low boiling point, coupled with its highly reactive nature, means that acetyl chloride must be handled with caution in laboratory settings. It is a colorless, fuming liquid with a pungent odor that is highly soluble in polar solvents like ethanol and acetone.
Acetyl Chloride Melting Point
C2H3ClO has a melting point of -112.1 °C (-169.8 °F) at standard atmospheric pressure. This makes it a highly volatile and reactive compound that requires careful handling and storage.
Acetyl Chloride Density g/mL
Acetyl chloride has a density of 1.104 g/mL at 25 °C (77 °F). This means that C2H3ClO is denser than water and will sink in it. The density of C2H3ClO is important in determining the amount of material that can be stored in a given volume, as well as the appropriate safety measures needed to handle and store the material.
Acetyl Chloride Molecular Weight
The molecular weight of C2H3ClO is 78.50 g/mol. This value is important in determining the amount of C2H3ClO needed in chemical reactions and for converting between different units of measurement.
Acetyl Chloride Structure
Acetyl chloride has a trigonal planar molecular geometry, with the carbon atom at the center surrounded by three other atoms in a flat triangular arrangement. The molecule has a C=O double bond between the carbon and oxygen atoms and a single bond between the carbon and chlorine atoms. The molecular structure of C2H3ClO gives it its characteristic reactivity and chemical properties.
Acetyl Chloride Formula
The chemical formula for acetyl chloride is C2H3ClO, which represents the number and type of atoms in the molecule. The formula is important for stoichiometric calculations in chemical reactions and for identifying the compound in laboratory settings. C2H3ClO is primarily used as a reagent in organic synthesis and as an acetylating agent in the production of pharmaceuticals and dyes.
| Appearance | Colorless liquid |
| Specific Gravity | 1.104 g/mL at 25°C |
| Color | Colorless |
| Odor | Pungent |
| Molar Mass | 78.50 g/mol |
| Density | 1.104 g/mL at 25°C |
| Melting Point | -112.1°C |
| Boiling Point | 51.5°C |
| Flash Point | -26°C |
| Water Solubility | Reacts violently with water |
| Solubility | Soluble in most organic solvents |
| Vapor Pressure | 69.7 mmHg at 25°C |
| Vapor Density | 2.7 (air=1) |
| pKa | -6.3 |
| pH | Highly acidic |
Acetyl Chloride Safety and Hazards
C2H3ClO is a highly reactive and hazardous substance that poses significant risks to human health and safety. It is a corrosive and toxic substance that can cause severe skin burns, eye damage, and respiratory irritation upon exposure. Acetyl chloride can also react violently with water, producing hydrochloric acid gas, which is a respiratory irritant. It is important to handle C2H3ClO with extreme care, wearing appropriate personal protective equipment, and using it only in a well-ventilated area. Proper storage, labeling, and transportation are also essential to prevent accidents and ensure the safe handling of this substance.
| Hazard Symbols | Corrosive, Toxic |
| Safety Description | Do not breathe vapor. Wear protective gloves and eye/face protection. In case of fire, use CO2, dry chemical, or foam extinguisher. |
| UN Ids | UN1717 |
| HS Code | 2915.90.9000 |
| Hazard Class | 8 |
| Packing Group | II |
| Toxicity | Highly toxic and corrosive. Causes severe skin and eye burns. Can be fatal if inhaled or ingested. |
Acetyl Chloride Synthesis Methods
C2H3ClO is produced by reacting acetic acid with thionyl chloride, phosphorus trichloride, or phosphorus pentachloride. These methods involve the use of highly reactive and hazardous reagents and should be carried out with extreme caution.
The most common method of synthesizing C2H3ClO involves the reaction of acetic acid with thionyl chloride. This method typically involves the addition of thionyl chloride to acetic acid in a controlled manner, with careful temperature control to prevent overheating and decomposition. The reaction produces C2H3ClO and sulfur dioxide gas as a byproduct.
Another method of synthesizing C2H3ClO involves the reaction of acetic acid with phosphorus trichloride or phosphorus pentachloride. In this method, acetic acid is mixed with the phosphorus trichloride or phosphorus pentachloride and heated to initiate the reaction. The reaction produces C2H3ClO and phosphoric acid as a byproduct.
It is important to note that these methods involve the use of highly reactive and hazardous chemicals and should be carried out only by experienced chemists in a well-ventilated area with appropriate personal protective equipment. Additionally, the synthesis of C2H3ClO should be carried out in a fume hood to minimize exposure to toxic and corrosive gases.
Acetyl Chloride Uses
Acetyl chloride is a versatile chemical compound that finds a variety of uses in industry and research. Some of the common uses of C2H3ClO are:
- Pharmaceuticals production: Various pharmaceuticals, including painkillers, antibiotics, and anesthetics, utilize C2H3ClO in their synthesis.
- Dyes and fragrances production: Production of various dyes and fragrances, such as coumarin used in perfumes and soaps, involves the use of C2H3ClO.
- Polymers production: The production of different polymers like polycarbonate and polyvinyl chloride relies on C2H3ClO as a reagent.
- Acetyl derivatives production: C2H3ClO plays a crucial role in producing acetyl derivatives of compounds like amino acids and alcohol.
- Chemical reactions: C2H3ClO exhibits high reactivity, making it a valuable reagent in a variety of chemical reactions, including acetylation reactions and Friedel-Crafts reactions.
- Laboratory research: C2H3ClO finds frequent application in laboratory research as a reagent for chemical reactions and as a solvent for various compounds.
It is important to note that C2H3ClO is a hazardous substance and should be handled with extreme caution. Proper safety protocols and regulations should be followed when using C2H3ClO to minimize the risks associated with its handling and use.