Benzoyl chloride

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Benzoyl chloride
Benzoyl chloride 200.svg
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
ECHA InfoCard 100.002.464 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-710-8
KEGG
PubChem CID
RTECS number
  • DM6600000
UNII
UN number 1736
  • InChI=1S/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H Yes check.svgY
    Key: PASDCCFISLVPSO-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H
    Key: PASDCCFISLVPSO-UHFFFAOYAL
  • ClC(=O)c1ccccc1
  • c1ccc(cc1)C(=O)Cl
Properties
C7H5ClO
Molar mass 140.57 g·mol−1
Appearancecolorless 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
Occupational safety and health (OHS/OSH):
Main hazards
Maybe harmful by ingestion and skin absorption; possible carcinogen [1]
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H302, H312, H314, H317, H332
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
0
W
Flash point 72 °C (162 °F; 345 K)
Safety data sheet (SDS) Fisher Scientific MSDS
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Preparation

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

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. [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:

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. [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, C6H5CO+. [8]

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

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

Related Research Articles

<span class="mw-page-title-main">Chloroacetic acid</span> Chemical compound

Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichloroacetic acid and trichloroacetic acid.

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

<span class="mw-page-title-main">Triphenylmethane</span> Chemical compound

Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).

<span class="mw-page-title-main">Aluminium chloride</span> Chemical compound

Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula AlCl3. It forms a hexahydrate with the formula [Al(H2O)6]Cl3, containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are colourless crystals, but samples are often contaminated with iron(III) chloride, giving them a yellow colour.

<span class="mw-page-title-main">Triphosgene</span> Chemical compound

Triphosgene (bis(trichloromethyl) carbonate (BTC) is a chemical compound with the formula OC(OCCl3)2. It is used as a solid substitute for phosgene, which is a gas. Triphosgene is stable up to 200 °C. Triphosgene is used in a variety of halogenation reactions.

<span class="mw-page-title-main">Acetyl chloride</span> Organic compound (CH₃COCl)

Acetyl chloride is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.

<span class="mw-page-title-main">Oxalyl chloride</span> Chemical compound

Oxalyl chloride is an organic chemical compound with the formula Cl−C(=O)−C(=O)−Cl. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis.

<span class="mw-page-title-main">Thionyl chloride</span> Inorganic compound (SOCl2)

Thionyl chloride is an inorganic compound with the chemical formula SOCl2. It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.

<span class="mw-page-title-main">Acryloyl chloride</span> Chemical compound

Acryloyl chloride, also known as 2-propenoyl chloride or acrylic acid chloride, is the organic compound with the formula CH2=CHCO(Cl). It is a colorless liquid, although aged samples appear yellow. It belongs to the acid chlorides group of compounds.

Geminal halide hydrolysis is an organic reaction. The reactants are geminal dihalides with a water molecule or a hydroxide ion. The reaction yields ketones from secondary halides or aldehydes from primary halides.

Stephen aldehyde synthesis, a named reaction in chemistry, was invented by Henry Stephen (OBE/MBE). This reaction involves the preparation of aldehydes (R-CHO) from nitriles (R-CN) using tin(II) chloride (SnCl2), hydrochloric acid (HCl) and quenching the resulting iminium salt ([R-CH=NH2]+Cl) with water (H2O). During the synthesis, ammonium chloride is also produced.

<span class="mw-page-title-main">Benzotrichloride</span> Chemical compound

Benzotrichloride (BTC), also known as α,α,α-trichlorotoluene, phenyl chloroform or (trichloromethyl)benzene, is an organic compound with the formula C6H5CCl3. Benzotrichloride is an unstable, colorless or somewhat yellowish, viscous, chlorinated hydrocarbon with a penetrating odor. Benzotrichloride is used extensively as a chemical intermediate for products of various classes, i.e. dyes and antimicrobial agents.

<span class="mw-page-title-main">Sulfenyl chloride</span> Chemical group (R–S–Cl)

In organosulfur chemistry, a sulfenyl chloride is a functional group with the connectivity R−S−Cl, where R is alkyl or aryl. Sulfenyl chlorides are reactive compounds that behave as sources of RS+. They are used in the formation of RS−N and RS−O bonds. According to IUPAC nomenclature they are named as alkyl thiohypochlorites, i.e. esters of thiohypochlorous acid.

<span class="mw-page-title-main">Butyryl chloride</span> Chemical compound

Butyryl chloride is an organic compound with the chemical formula CH3CH2CH2C(O)Cl. It is a colorless liquid with a pungent odor. Butyryl chloride is soluble in aprotic organic solvents, but it reacts readily with water and alcohols. It is usually produced by chlorination of butyric acid.

In organic chemistry, thiocarboxylic acids or carbothioic acids are organosulfur compounds related to carboxylic acids by replacement of one of the oxygen atoms with a sulfur atom. Two tautomers are possible: a thione form and a thiol form. These are sometimes also referred to as "carbothioic O-acid" and "carbothioic S-acid" respectively. Of these the thiol form is most common.

<span class="mw-page-title-main">Imidoyl chloride</span>

Imidoyl chlorides are organic compounds that contain the functional group RC(NR')Cl. A double bond exist between the R'N and the carbon centre. These compounds are analogues of acyl chloride. Imidoyl chlorides tend to be highly reactive and are more commonly found as intermediates in a wide variety of synthetic procedures. Such procedures include Gattermann aldehyde synthesis, Houben-Hoesch ketone synthesis, and the Beckmann rearrangement. Their chemistry is related to that of enamines and their tautomers when the α hydrogen is next to the C=N bond. Many chlorinated N-heterocycles are formally imidoyl chlorides, e.g. 2-chloropyridine, 2, 4, and 6-chloropyrimidines.

<span class="mw-page-title-main">Propionyl chloride</span> Chemical compound

Propionyl chloride (also propanoyl chloride) is the organic compound with the formula CH3CH2C(O)Cl. It is the acyl chloride derivative of propionic acid. It undergoes the characteristic reactions of acyl chlorides. It is a colorless, corrosive, volatile liquid.

<span class="mw-page-title-main">Pentanoyl chloride</span> Chemical compound

Pentanoyl chloride is an acyl chloride derived from pentanoic acid. It is a colorless liquid that is used to attach the valeroyl group. It is usually produced by chlorination of valeric acid.

Lauroyl chloride is the organic compound with the formula CH3(CH2)10COCl. It is the acid chloride of lauric acid. Lauroyl chloride is a standard reagent for installing the lauroyl group. It is mainly produced as a precursor to dilauroyl peroxide, which is widely used in free-radical polymerizations.

References

  1. Benzoyl chloride: toxicity and precautions
  2. Maki, Takao; Takeda, Kazuo (2000). "Benzoic Acid and Derivatives". 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. hdl: 2027/hvd.hxdg3f .
  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. 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.