Chemistry:Benzoyl chloride

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Short description: Organochlorine compound (C7H5ClO)
Benzoyl chloride
Benzoyl Chloride
Benzoyl-chloride-from-xtal-3D-bs-17.png
Benzoyl-chloride-from-xtal-3D-sf.png
Names
Preferred IUPAC name
Benzoyl chloride
Other names
Benzoic acid chloride (1:1)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 202-710-8
KEGG
RTECS number
  • DM6600000
UNII
UN number 1736
Properties
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)
reacts, forms hydrogen chloride on contact with water
-75.8·10−6 cm3/mol
Hazards
Main hazards Maybe harmful by ingestion and skin absorption; possible carcinogen[1]
Safety data sheet Fisher Scientific MSDS
GHS pictograms GHS05: CorrosiveGHS07: Harmful
GHS Signal word Danger
H302, H312, H314, H317, H332
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)
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 fuelHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acidNFPA 704 four-colored diamond
2
3
0
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).
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Infobox references
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Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C
7
H
5
ClO
. It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring (C
6
H
6
) 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.

Preparation

Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid:[2]

C
6
H
5
CCl
3
+ H
2
O → C
6
H
5
COCl + 2 HCl
C
6
H
5
CCl
3
+ C
6
H
5
CO
2
H → 2 C
6
H
5
COCl + 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.[3]

An early method for production of benzoyl chloride involved chlorination of benzyl alcohol.[4]

Reactions

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

C
6
H
5
COCl + H
2
O → C
6
H
5
COOH + 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.[5][6]

It undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding benzophenones and related derivatives.[7] With carbanions, it serves again as a source of the benzoyl cation synthon, C
6
H
5
CO+
.[8]

Benzoyl peroxide, a common reagent in polymer chemistry, is produced industrially by treating benzoyl chloride with hydrogen peroxide and sodium hydroxide:[9]

2 C
6
H
5
COCl + H
2
O
2
+ 2 NaOH → (C
6
H
5
CO)
2
O
2
+ 2 NaCl + 2 H
2
O

References

  1. Benzoyl chloride: toxicity and precautions
  2. Maki, Takao; Takeda, Kazuo (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555. 
  3. Friedrich Wöhler, Justus von Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie 3 (3): 262–266. doi:10.1002/jlac.18320030302. 
  4. US1851832, 29 March 1932
  5. Marvel, C. S.; Lazier, W. A. (1929). "Benzoyl Piperidine". Organic Syntheses 9: 16. doi:10.15227/orgsyn.009.0016. 
  6. 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).
  7. Minnis, Wesley (1932). "Phenyl Thienyl Ketone". Organic Syntheses 12: 62. doi:10.15227/orgsyn.012.0062. 
  8. 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. 
  9. Template:Cite tech report

External links