Acetyl chloride
From Wikipedia, the free encyclopedia
| Acetyl chloride | |
|---|---|
 |
 |
 |
|
| IUPAC name | Ethanoyl chloride |
| Other names | Acetyl chloride |
| Identifiers | |
| CAS number | [75-36-5] |
| RTECS number | AO6390000 |
| SMILES | CC(=O)Cl |
| Properties | |
| Molecular formula | CH3COCl |
| Molar mass | 78.5 g/mol |
| Appearance | colorless liquid |
| Density | 1.11 g/ml, liquid |
| Melting point |
−112 °C |
| Boiling point |
51 °C |
| Solubility in water | Reacts |
| Structure | |
| Dipole moment | 2.45 D |
| Hazards | |
| EU classification | Flammable (F) Corrosive (C) |
| R-phrases | R11, R14, R34 |
| S-phrases | (S1/2), S9, S16, S26, S45 |
| Flash point | 5 °C |
| Autoignition temperature |
390 °C |
| Explosive limits | 7.3–19% |
| Related compounds | |
| Related acyl chlorides | Propionyl chloride Butyryl chloride |
| Related compounds | Acetic acid Acetic anhydride |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
Acetyl chloride, also known as ethanoyl chloride, is an acid chloride (also known as an acyl chloride) derived from acetic acid (ethanoic acid). It has the formula CH3COCl and it belongs to the class of organic compounds called acyl halides. At room temperature and pressure, it is a clear colorless liquid. Acetyl chloride does not exist in nature, because contact with water would hydrolyze it into acetic acid and hydrogen chloride. In fact, if handled in open air it gives of white smoke owing to the hydrolysis from the moisture in the air. The smoke is actually gaseous hydrogen chloride which forms small droplets in the air with water vapour.
Contents |
[edit] Synthesis
Acetyl chloride is synthesized by the reaction of acetic acid (CH3COO-H) with thionyl chloride (O=SCl2) under liberation of sulfur dioxide (SO2).
- CH3COO-H + O=SCl2 → CH3COCl + SO2 + H-Cl
[edit] Uses
It is a reagent for acetylation in the synthesis or derivatization of chemical compounds. Examples of acetylation reactions include acylation processes such as esterification (see below) and the Friedel-Crafts reaction).
- CH3COCl + HO-CH2-CH3 → CH3-COO-CH2-CH3 + H-Cl
Frequently such acylations are carried out in the presence of a base such as pyridine, triethylamine, or DMAP, which as catalysts help to promote the reaction and as bases neutralize the resulting HCl.
Acetylation is the introduction of an acetyl group via acylation using a reactant such as acetyl chloride or acetic anhydride. An acetyl group is an acyl group having the formula
- -C(=O)-CH3
For further information on the types of chemical reactions compounds such as acetyl chloride can undergo, see acyl halide.
[edit] References
 |
This article does not cite any references or sources. (September 2007) Please help improve this article by adding citations to reliable sources. Unverifiable material may be challenged and removed. |
