Benzoyl chloride

Benzoyl chloride
Names
	Preferred IUPAC name Benzoyl chloride
Identifiers
CAS Number	98-88-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:82275;
ChEMBL	ChEMBL2260719;
ChemSpider	7134 ;
ECHA InfoCard	100.002.464
EC Number	202-710-8;
KEGG	C19168 ;
PubChem CID	7412;
RTECS number	DM6600000;
UNII	VTY8706W36;
UN number	1736
CompTox Dashboard (EPA)	DTXSID9026631 ;
	InChI InChI=1S/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H Key: PASDCCFISLVPSO-UHFFFAOYSA-N ; InChI=1/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H Key: PASDCCFISLVPSO-UHFFFAOYAL;
	SMILES ClC(=O)c1ccccc1; c1ccc(cc1)C(=O)Cl;
Properties
Chemical formula	C7H5ClO
Molar mass	140.57 g·mol−1
Appearance	colorless liquid
Odor	Benzaldehyde like but more pungent
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
Magnetic susceptibility (χ)	-75.8·10−6 cm3/mol
Hazards
Safety data sheet	Fisher Scientific MSDS
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H312, H314, H317, H332
GHS precautionary statements	P260, P261, P264, P270, P271, P272, P280, P301+312, P301+330+331, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P310, P312, P321, P322, P330, P333+313, P363, P405, P501
NFPA 704 (fire diamond)	2 3 0 W
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).
	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 preparation 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 with 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.[2]

An early method for production of benzoyl chloride involved chlorination of benzyl alcohol.[3]

Reactions

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

C₆H₅COCl + H₂O → C₆H₅CO₂H + HCl

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.[4][5]

It undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding benzophenones and related derivatives.[6] With carbanions, it serves again as a source of "PhCO⁺".[7]

Benzoyl peroxide, a common reagent in polymer chemistry, is produced industrially by treating benzoyl chloride with hydrogen peroxide and sodium hydroxide:[8]

2 C₆H₅COCl + H₂O₂ + 2 NaOH → (C₆H₅CO)₂O₂ + 2 NaCl + 2 H₂O

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References

Maki, Takao; Takeda, Kazuo (2000). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555.
Friedrich Wöhler, Justus von Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie. 3 (3): 262–266. doi:10.1002/jlac.18320030302. hdl:2027/hvd.hxdg3f.
US1851832, 29 March 1932
Marvel, C. S.; Lazier, W. A. (1929). "Benzoyl Piperidine". Organic Syntheses. 9: 16. doi:10.15227/orgsyn.009.0016.
Prasenjit Saha, Md Ashif Ali, and Tharmalingam Punniyamurthy "Ligand-free Copper(ii) Oxide Nanoparticles Catalyzed Synthesis Of Substituted Benzoxazoles" Org. Synth. 2011, volume 88, pp. 398. doi:10.15227/orgsyn.088.0398. (an illustrative reaction of an amine with benzoyl chloride).
Minnis, Wesley (1932). "Phenyl Thienyl Ketone". Organic Syntheses. 12: 62. doi:10.15227/orgsyn.012.0062.
Fujita, M.; Hiyama, T. (1990). "Directed Reduction of a beta-keto Amide: Erythro-1-(3-hydroxy-2-methyl-3-phenylpropanoyl)piperidine". Organic Syntheses. 69: 44. doi:10.15227/orgsyn.069.0044.
El-Samragy, Yehia (2004). "Chemical and Technical Assessment". Benzoyl Peroxide (PDF). 61st JECFA (Technical report). Joint FAO/WHO Expert Committee on Food Additives. p. 1. Retrieved 31 October 2013.

External links

International Chemical Safety Card 1015

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[1] Maki, Takao; Takeda, Kazuo (2000). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555.

[2] Friedrich Wöhler, Justus von Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie. 3 (3): 262–266. doi:10.1002/jlac.18320030302. hdl:2027/hvd.hxdg3f.

[3] US1851832, 29 March 1932

[4] Marvel, C. S.; Lazier, W. A. (1929). "Benzoyl Piperidine". Organic Syntheses. 9: 16. doi:10.15227/orgsyn.009.0016.

[5] Prasenjit Saha, Md Ashif Ali, and Tharmalingam Punniyamurthy "Ligand-free Copper(ii) Oxide Nanoparticles Catalyzed Synthesis Of Substituted Benzoxazoles" Org. Synth. 2011, volume 88, pp. 398. doi:10.15227/orgsyn.088.0398. (an illustrative reaction of an amine with benzoyl chloride).

[6] Minnis, Wesley (1932). "Phenyl Thienyl Ketone". Organic Syntheses. 12: 62. doi:10.15227/orgsyn.012.0062.

[7] Fujita, M.; Hiyama, T. (1990). "Directed Reduction of a beta-keto Amide: Erythro-1-(3-hydroxy-2-methyl-3-phenylpropanoyl)piperidine". Organic Syntheses. 69: 44. doi:10.15227/orgsyn.069.0044.

[FAO-8] El-Samragy, Yehia (2004). "Chemical and Technical Assessment". Benzoyl Peroxide (PDF). 61st JECFA (Technical report). Joint FAO/WHO Expert Committee on Food Additives. p. 1. Retrieved 31 October 2013.