Benzoyl Chloride - Wikipedia

Organochlorine compound (C7H5ClO) Not to be confused with benzyl chloride. Benzoyl chloride

Names
Preferred IUPAC name Benzoyl chloride
Other names Benzoic acid chloride (1:1) alpha-Chlorobenzaldehyde Benzene carbonyl chloride
Identifiers
CAS Number	98-88-4 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:82275
ChEMBL	ChEMBL2260719
ChemSpider	7134 Y
ECHA InfoCard	100.002.464
EC Number	202-710-8
KEGG	C19168 Y
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 YKey: PASDCCFISLVPSO-UHFFFAOYSA-N Y InChI=1/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5HKey: PASDCCFISLVPSO-UHFFFAOYAL
SMILES ClC(=O)c1ccccc1 c1ccc(cc1)C(=O)Cl
Properties
Chemical formula	C6H5COCl
Molar mass	140.57 g·mol−1
Appearance	colorless liquid
Odor	Benzaldehyde-like, but more pungent
Density	1.211 g/mL[1]
Melting point	−1 °C (30 °F; 272 K)[1]
Boiling point	198 °C (388 °F; 471 K)[1]
Solubility in water	Reacts. Decomposes to HCl and benzoic acid.
Vapor pressure	1 hPa (0.75 mmHg) (32 °C (90 °F; 305 K))[1]
Magnetic susceptibility (χ)	−75.8×10−6 cm3/mol
Viscosity	0.0012 Pa·s[2]
Structure
Point group	Cs
Hazards
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H227, H302+H312, H314, H317, H331, H402
Precautionary statements	P210, P261, P264, P270, P271, P272, P273, P280, P301+P312+P330, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310, P333+P313, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)	[2] 3 2 2W
Flash point	72 °C (162 °F; 345 K)[1]
Autoignitiontemperature	600 °C (1,112 °F; 873 K)[1]
Explosive limits	2.5% to 27%(V)[1]
Threshold limit value (TLV)	0.5 ppm[2] (C)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	1920 mg/kg (Oral, rat)[2] 1112 mg/kg (Dermal, rabbit)[2]
LC50 (median concentration)	3.03 mg/L (Inhalation, rat, 4h)[2]
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). Y verify (what is YN ?) Infobox references

Chemical compound

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, and consists of a phenyl ring (C6H5) with an acyl chloride (−C(=O)Cl) substituent. It is mainly useful for the production of organic peroxides but is also used in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.[3]

Preparation

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Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid:[3]

C6H5CCl3 + H2O → C6H5COCl + 2 HCl C6H5CCl3 + C6H5CO2H → 2 C6H5COCl + HCl

As with other acyl chlorides, it can be generated from the parent acid and standard chlorinating agents such as phosphorus pentachloride, thionyl chloride, and oxalyl chloride. It was first prepared by treatment of benzaldehyde with chlorine.[4]

An early method for production of benzoyl chloride involved chlorination of benzyl alcohol.[5][better source needed]

Reactions

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

C6H5COCl + H2O → C6H5COOH + 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.[6][7]

It undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding benzophenones and related derivatives.[8] With carbanions, it serves again as a source of the benzoyl cation synthon, C6H5CO+.[9]

Benzoyl peroxide, a common reagent in polymer chemistry, is produced industrially by treating benzoyl chloride with hydrogen peroxide and sodium hydroxide:[10]

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

Modified benzoyl chlorides

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Many substituted derivatives of benzoyl chloride are known. 4-Nitrobenzoyl chloride is a precursor to the anesthetic procaine.[3] One example is 4-chlorobenzoyl chloride, a precursor to 4-chloro-4'-hydroxybenzophenone, which is used to make high performance polymers.[11]

Safety

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Benzoyl chloride is toxic and a serious skin irritant.[3]

See also

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• Benzoyl fluoride

References

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1. ^ a b c d e f g h Sigma-Aldrich Co., Benzoyl chloride. Retrieved on 3 January 2026.
2. ^ a b c d e f "Benzoyl chloride SDS". thermofisher.com. ThermoFisher. 21 December 2025. p. 5. Retrieved 3 January 2026.
3. ^ a b c d Maki, Takao; Takeda, Kazuo (2000). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555. ISBN 978-3-527-30673-2.
4. ^ Wöhler, Friedrich; von Liebig, Justus (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie (in German). 3 (3): 262–266. doi:10.1002/jlac.18320030302. hdl:2027/hvd.hxdg3f.
5. ^ US patent 1851832, Wilmot, H.B. & Garnett, P.J., "Manufacture and production of benzoyl chloride", published 1932-03-29, issued 1932-03-29 
6. ^ Marvel, C. S.; Lazier, W. A. (1929). "Benzoyl Piperidine". Organic Syntheses. 9: 16. doi:10.15227/orgsyn.009.0016; Collected Volumes, vol. 1, 1941, p. 99.
7. ^ Saha, P.; Ali, M. A.; Punniyamurthy, T. (2011). "Ligand-free Copper(ii) Oxide Nanoparticles Catalyzed Synthesis Of Substituted Benzoxazoles". Organic Syntheses. 88: 398–405. doi:10.15227/orgsyn.088.0398.
8. ^ Minnis, W. (1932). "Phenyl Thienyl Ketone". Organic Syntheses. 12: 62. doi:10.15227/orgsyn.012.0062; Collected Volumes, vol. 2, 1943.
9. ^ Fujita, M.; Hiyama, T. (1990). "Phenyl Thienyl Ketone". Organic Syntheses. 69: 44. doi:10.15227/orgsyn.069.0044; Collected Volumes, vol. 8, 1993.
10. ^ 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. Benzoyl peroxide is synthesized commercially by the reaction of benzoyl chloride, sodium hydroxide, and hydrogen peroxide. Traces of benzoic acid remain after usual purification procedures.
11. ^ Parker, David; Bussink, Jan; Van De Grampel, Hendrik T.; Wheatley, Gary W.; Dorf, Ernst-Ulrich; Ostlinning, Edgar; Reinking, Klaus; Schubert, Frank; Jünger, Oliver; Wagener, Reinhard (2012). "Polymers, High-Temperature". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a21_449.pub4. ISBN 978-3-527-30673-2.

External links

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Authority control databases	GND