Benzoyl chloride

Benzoyl chloride
Names
	IUPAC name Benzoyl chloride
Identifiers
CAS Number	98-88-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	7134;
ECHA InfoCard	100.002.464
PubChem CID	7412;
RTECS number	DM6600000;
CompTox Dashboard (EPA)	DTXSID9026631 ;
	InChI InChI=1/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H Key: PASDCCFISLVPSO-UHFFFAOYAL;
	SMILES ClC(=O)c1ccccc1;
Properties
Chemical formula	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)
Solubility in water	reacts
Hazards
Flash point	72 °C
Related compounds
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 production of dyes, perfumes, pharmaceuticals, and resins.

Preparation

Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid:^[1]

C₆H₅CCl₃ + H₂O → C₆H₅COCl + 2 HCl

C₆H₅CCl₃ + C₆H₅CO₂H → 2 C₆H₅COCl + HCl

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 benzoic acid with chlorine.^[2]

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:

C₆H₅COCl + H₂O → C₆H₅CO₂H + HCl

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

2 C₆H₅COCl + Na₂O₂ → (C₆H₅CO)₂O₂ + 2 NaCl

References

^ Takao Maki, Kazuo Takeda “Benzoic Acid and Derivatives” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_555
^ "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie. 3: 249–282. 1832. doi:10.1002/jlac.18320030302. {{cite journal}}: Unknown parameter |authors= ignored (help)

External links

International Chemical Safety Card 1015

[1] Takao Maki, Kazuo Takeda “Benzoic Acid and Derivatives” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_555

[2] "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie. 3: 249–282. 1832. doi:10.1002/jlac.18320030302. {{cite journal}}: Unknown parameter |authors= ignored (help)

[1]

[2]