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)
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	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, forms hydrogen chloride on contact with water
Magnetic susceptibility (χ)	−75.8·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	harmful by ingestion and skin absorption
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H312, H314, H317, H332
Precautionary statements	P260, P261, P264, P270, P271, P272, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P363, P405, P501
NFPA 704 (fire diamond)	3 2 0W
Flash point	72 °C (162 °F; 345 K)
Safety data sheet (SDS)	Fisher Scientific MSDS
Structure
Point group	Cs
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 C7H5ClO. It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring (C6H6) with an acyl chloride (−C(=O)Cl) substituent. 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.[1]

Preparation

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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 standard chlorinating agents such as phosphorus pentachloride, thionyl chloride, and oxalyl 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

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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.[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 the benzoyl cation synthon, C6H5CO+.[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

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.[1] One example is 4-chlorobenzoyl chloride, a precursor to 4-chloro-4'-hydroxybenzophenone, which is used to make high performance polymers.[9]

Safety

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Benzoyl chloride is toxic and a serious skin irritant.[1]

See also

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• Benzoyl fluoride

References

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1. ^ a b c d Maki, Takao; Takeda, Kazuo (2000). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_555. ISBN 978-3-527-30385-4.
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.
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.
9. ^ 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. doi:10.1002/14356007.a21_449.pub4. ISBN 978-3-527-30673-2.

External links

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• International Chemical Safety Card 1015

Authority control databases	GND