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Acetyl chloride



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. 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. 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.

Additional recommended knowledge

It is chemically synthesized by the reaction of acetic acid with thionyl chloride.

CH3COO-H + O=SCl2 → CH3COCl + 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 (see below) and the Friedel-Crafts reaction).

CH3COCl + HO-CH2-CH3CH3-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.

References

     
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Acetyl_chloride". A list of authors is available in Wikipedia.
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