*** Welcome to piglix ***

Benzoyl chloride

Benzoyl chloride
Benzoyl Chloride
Benzoyl-chloride-3D-balls.png
Benzoyl-chloride-3D-vdW.png
Names
Preferred IUPAC name
Benzoyl chloride
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.002.464
KEGG
PubChem CID
RTECS number DM6600000
Properties
C7H5ClO
Molar mass 140.57 g·mol−1
Appearance colorless liquid
Density 1.21 g/mL, liquid
Melting point −1 °C (30 °F; 272 K)
Boiling point 197.2 °C (387.0 °F; 470.3 K)
reacts
-75.8·10−6 cm3/mol
Hazards
Safety data sheet Fisher Scientific MSDS
Toxic T Corrosive C
R-phrases R34
S-phrases (S1/2) S26 S45
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 72 °C (162 °F; 345 K)
Related compounds
Related compounds
 benzoic acid, benzoic anhydride, benzaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C6H5COCl. It is a colourless, fuming liquid with an irritating odour. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid:

As for other acyl chlorides, it can be generated from the parent acid and other chlorinating agents phosphorus pentachloride or thionyl chloride. It was first prepared by treatment of benzaldehyde with chlorine.

An early method for production of benzoyl chloride involved chlorination of benzyl alcohol.

It reacts with water to produce hydrochloric acid and benzoic acid:

Benzoyl chloride is a typical acyl chloride. It reacts with alcohols to give the corresponding esters. Similarly, it reacts with amines to give the amide.

It undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding benzophenones and related derivatives. With carbanions, it serves again as a source of "PhCO+".

Benzoyl peroxide, a common reagent in polymer chemistry, is produced industrially by treating benzoyl chloride with hydrogen peroxide and sodium hydroxide:


...
Wikipedia

...