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Acetyl chloride
From Wikipedia, the free encyclopedia
| Acetyl chloride | |
|---|---|
 |
|
| General | |
| Systematic name | Ethanoyl chloride |
| Other names | Acetyl chloride |
| Molecular formula | CH3COCl |
| SMILES | CC(=O)Cl |
| Molar mass | 78.5 g/mol |
| Appearance | colorless liquid |
| CAS number | [75-36-5] |
| Properties | |
| Density and phase | 1.11 g/ml, liquid |
| Solubility in water | Reacts |
| Melting point | −112 °C |
| Boiling point | 51 °C |
| Viscosity | ? cP at ? °C |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Flammable (F) Corrosive (C) |
| NFPA 704 |
3
3
2
|
| 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% |
| RTECS number | AO6390000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| 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 H3C-COCl and it belongs to the class of organic compounds called acyl halides. The chemical structure of acetyl chloride is shown at right. 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.
It is chemically synthesized by the reaction of thionyl chloride with acetic acid.
and is used as 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).
- H3C-COCl + HO-CH2-CH3 → H3C-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.