Benzoyl chloride

Benzoyl chloride
IUPAC name	Benzoyl chloride
Identifiers
CAS number	98-88-4 Y
PubChem	7412
RTECS number	DM6600000
SMILES	ClC(=O)c1ccccc1
InChI	1/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H
InChI key	PASDCCFISLVPSO-UHFFFAOYAL
ChemSpider ID	7134
Properties
Molecular formula	C7H5ClO
Molar mass	140.57 g mol−1
Appearance	colorless liquid
Density	1.21 g/mL, liquid
Melting point	-1 °C, 272 K, 30 °F
Boiling point	197.2 °C, 470 K, 387 °F
Solubility in water	reacts
Hazards
MSDS	Oxford MSDS
EU classification	T C
R-phrases	R34
S-phrases	(S1/2) S26 S45
Flash point	72 °C
Related compounds
Related compounds	benzoic acid, benzoic anhydride, benzaldehyde
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Benzoyl chloride, also known as benzenecarbonyl chloride, is a colourless, fuming liquid with an irritating odour.

This substance is used as an intermediate chemical in the preparation of dyes, perfumes, peroxides, pharmaceuticals, and resins. It is also used in photography; as gasoline gum inhibitors, and in the manufacture of synthetic tannins. It was formerly employed as an irritant gas in chemical warfare.

Preparation

Preparation of benzoyl chlorides is similar to that of other acyl chlorides: by reacting benzoic acid (C₆H₅COOH) with phosphorus pentachloride or thionyl chloride. Alternatively, it may be prepared by chlorinating benzaldehyde;^[1] this is an industrial process.^{[citation needed]}

Reactions

Benzoyl chloride is a typical acyl chloride. It reacts with alcohols and amines to give the corresponding esters and amides. It undergoes the Friedel-Crafts acylation with arenes to give the corresponding benzophenones. Similarly, it reacts with water to produce hydrochloric acid and benzoic acid:

PhCOCl + H₂O → PhCOOH + HCl

Benzoyl chloride reacts with sodium peroxide to give benzoyl peroxide and sodium chloride:^{[citation needed]}

2 PhCOCl + Na₂O₂ → (PhCO)₂O₂ + 2 NaCl

References

1. ^ Friedrich Wöhler; Justus von Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie 3: 249. doi:10.1002/jlac.18320030302. 

External links

• International Chemical Safety Card 1015