Benzoyl chloride: Difference between revisions

{{Short description|Organochlorine compound (C7H5ClO)}}

| Watchedfields = changed

| verifiedrevid = 443944420

| ImageFile = Benzoyl chloride 200.svg

| ImageFileL1 = Benzoyl-chloride-from-xtal-3D-bs-17.png

| ImageFileR1 = Benzoyl-chloride-from-xtal-3D-sf.png

| PIN = Benzoyl chloride

| OtherNames = Benzoic acid chloride (1:1)

|Section1={{Chembox Identifiers

| InChI = 1/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H

| PubChem = 7412

| SMILES = ClC(=O)c1ccccc1

| RTECS = DM6600000

| EC_number = 202-710-8

| UNNumber = 1736

| UNII = VTY8706W36

| ChEBI = 82275

| ChEMBL = 2260719

|Section2={{Chembox Properties

| C=7 | H=5 | Cl=1 | O=1

| Appearance = colorless liquid

| Odor = Benzaldehyde like but more pungent

| Density = 1.21 g/mL, liquid

| MeltingPtC = -1

| BoilingPtC = 197.2

| Solubility = reacts, forms [[hydrogen chloride]] on contact with [[water]]

| MagSus = -75.8·10⁻⁶ cm³/mol

|Section3={{Chembox Hazards

| MainHazards= Maybe harmful by ingestion and skin [[Absorption (skin)|absorption]]; possible carcinogen<ref>Benzoyl chloride: toxicity and precautions</ref>

| ExternalSDS = [https://fscimage.fishersci.com/msds/95451.htm Fisher Scientific MSDS]

| GHSPictograms = {{GHS05}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|302|312|314|317|332}}

| PPhrases = {{P-phrases|260|261|264|270|271|272|280|301+312|301+330+331|302+352|303+361+353|304+312|304+340|305+351+338|310|312|321|322|330|333+313|363|405|501}}

| FlashPtC = 72

| NFPA-H = 3

| NFPA-F = 2

| NFPA-R = 0

| NFPA-S = W

| AutoignitionPtC =

|Section8={{Chembox Related

| OtherFunction_label = [[acyl chloride]]

| OtherCompounds = [[benzoic acid]], [[benzoic anhydride]], [[benzaldehyde]]}}

'''Benzoyl chloride''', also known as '''benzenecarbonyl chloride''', is an [[organochlorine compound]] with the formula {{chem2|C7H5ClO}}. It is a colourless, fuming liquid with an irritating odour, and consists of a [[benzene]] ring ({{chem2|C6H6}}) with an [[acyl chloride]] ({{chem2|\sC(\dO)Cl}}) [[substituent]]. It is mainly useful for the [[Product (chemistry)|product]]ion of [[organic peroxide|peroxide]]s but is generally useful in other [[area]]s such as in the preparation of [[dye]]s, [[perfume]]s, [[pharmaceutical]]s, and [[resin]]s.

Benzoyl chloride is produced from [[benzotrichloride]] using either water or benzoic acid:<ref>{{Ullmann |doi=10.1002/14356007.a03_555|title=Benzoic Acid and Derivatives|year=2000|last1=Maki|first1=Takao|last2=Takeda|first2=Kazuo|isbn=3527306730}}</ref>

:{{chem2|C6H5CCl3 + H2O -> C6H5COCl + 2 HCl }}

:{{chem2|C6H5CCl3 + C6H5CO2H -> 2 C6H5COCl + HCl }}

As with other [[acyl chloride]]s, 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.<ref>{{cite journal | doi = 10.1002/jlac.18320030302 | title = Untersuchungen über das Radikal der Benzoesäure | year = 1832 | journal = [[Annalen der Pharmacie]] | volume = 3 | issue = 3 | pages = 262–266 | author = [[Friedrich Wöhler]], [[Justus von Liebig]] | hdl = 2027/hvd.hxdg3f | hdl-access = free }}</ref>

An early method for production of benzoyl chloride involved [[chlorination reaction|chlorination]] of [[benzyl alcohol]].<ref>[http://www.google.com/patents/US1851832 US1851832], 29 March 1932</ref>

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

:{{chem2|C6H5COCl + H2O -> C6H5COOH + HCl }}

Benzoyl chloride is a typical [[acyl chloride]]. It reacts with [[Alcohol (chemistry)|alcohol]]s to give the corresponding [[ester]]s. Similarly, it reacts with [[Amine|amines]] to give the [[amide]].<ref>{{cite journal|first1=C. S.|last1=Marvel|first2=W. A.|last2=Lazier|title=Benzoyl Piperidine|journal=Organic Syntheses|year=1929|volume=9|page=16|doi=10.15227/orgsyn.009.0016}}</ref><ref>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).</ref>

It undergoes the [[Friedel-Crafts acylation]] with [[aromatic compounds]] to give the corresponding [[benzophenone]]s and related derivatives.<ref>{{cite journal|first1=Wesley|last1=Minnis|doi=10.15227/orgsyn.012.0062|title=Phenyl Thienyl Ketone|journal=Organic Syntheses|year=1932|volume=12|page=62}}</ref> With carbanions, it serves again as a source of the benzoyl cation [[synthon]], {{chem2|C6H5CO+}}.<ref>{{cite journal|doi=10.15227/orgsyn.069.0044|title=Directed Reduction of a beta-keto Amide: Erythro-1-(3-hydroxy-2-methyl-3-phenylpropanoyl)piperidine|journal=Organic Syntheses|year=1990|volume=69|page=44|first1=M.|last1=Fujita|first2=T.|last2=Hiyama}}</ref>

[[Benzoyl peroxide]], a common reagent in [[polymer chemistry]], is produced industrially by treating benzoyl chloride with [[hydrogen peroxide]] and [[sodium hydroxide]]:<ref name="FAO">{{cite tech report

| last = El-Samragy

| first = Yehia

| year =2004

| title =Benzoyl Peroxide

| periodical =61st JECFA

| article =Chemical and Technical Assessment

| publisher =Joint FAO/WHO Expert Committee on Food Additives

| page =1

| url =http://www.fao.org/fileadmin/templates/agns/pdf/jecfa/cta/63/Benzoylperoxide.pdf

| accessdate =31 October 2013

| format =PDF

<!-- | quote =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. -->

}}</ref>

:{{chem2|2 C6H5COCl + H2O2 + 2 NaOH -> (C6H5CO)2O2 + 2 NaCl + 2 H2O }}

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[[Category:Benzene derivatives]]