Acetyl chloride
Acetyl chloride, also known as ethanoyl chloride, is an
acid chloride derived from
acetic 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.
Encyclopedia
| Acetyl chloride |
|---|
| |
| General |
|---|
| Systematic name | Ethanoyl chloride |
| Other names | Acetyl chloride |
| Molecular formula | CH3COCl |
| SMILES | CCCl |
| 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
Corrosive |
| NFPA 704 | |
| R-phrases | , , |
| S-phrases | , , , , |
| Flash point | 5 °C |
| Autoignition temperature | 390 °C |
| Explosive limits | 7.3–19% |
| RTECS number | AO6390000 |
| Supplementary data page |
|---|
Structure and
properties | n, er, 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
|
|
Acetyl chloride, also known as
ethanoyl chloride, is an
acid chloride derived from
acetic acid. It has the formula H
3C-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.
- H3C-COO-H + O=SCl2 ? H3C-COCl + SO2 + H-Cl
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 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-CH3.
For further information on the types of chemical reactions compounds such as acetyl chloride can undergo, see
acyl halide.
External links
