Benzoyl chloride का स्रोत देखें

{{distinguish|benzyl chloride}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 443944420
| ImageFile = Benzoyl Chloride.png
| ImageSize = 120px
| ImageName = Benzoyl Chloride
| ImageFileL1 = Benzoyl-chloride-from-xtal-3D-bs-17.png
| ImageFileR1 = Benzoyl-chloride-from-xtal-3D-sf.png
| PIN = Benzoyl chloride
| OtherNames = 
|Section1={{Chembox Identifiers
| InChI = 1/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H
| InChIKey = PASDCCFISLVPSO-UHFFFAOYAL
| SMILES1 = c1ccc(cc1)C(=O)Cl
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PASDCCFISLVPSO-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 98-88-4
| PubChem = 7412
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C19168
| SMILES = ClC(=O)c1ccccc1
| RTECS = DM6600000
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=7134
| 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
| MagSus = -75.8·10<sup>−6</sup> cm<sup>3</sup>/mol
  }}
|Section3={{Chembox Hazards
| 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 C<sub>7</sub>H<sub>5</sub>ClO. It is a colourless, fuming liquid with an irritating odour.  It is mainly useful for the production of [[organic peroxide|peroxide]]s but is generally useful in other areas such as in the preparation of [[dye]]s, [[perfume]]s, [[pharmaceutical]]s, and [[resin]]s.

==Preparation==
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>
:C<sub>6</sub>H<sub>5</sub>CCl<sub>3</sub>  +  H<sub>2</sub>O   →   C<sub>6</sub>H<sub>5</sub>COCl  +  2 HCl
:C<sub>6</sub>H<sub>5</sub>CCl<sub>3</sub>  +  C<sub>6</sub>H<sub>5</sub>CO<sub>2</sub>H   →   2 C<sub>6</sub>H<sub>5</sub>COCl  +  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>

==Reactions==
It reacts with water to produce [[hydrochloric acid]] and [[benzoic acid]]:
: C<sub>6</sub>H<sub>5</sub>COCl  +  H<sub>2</sub>O   →  C<sub>6</sub>H<sub>5</sub>COOH  +  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]], C<sub>6</sub>H<sub>5</sub>CO<sup>+</sup>.<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 techreport
| 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>
:2 C<sub>6</sub>H<sub>5</sub>COCl  +  H<sub>2</sub>O<sub>2</sub>  +  2 NaOH   →   (C<sub>6</sub>H<sub>5</sub>CO)<sub>2</sub>O<sub>2</sub>  +  2 NaCl  +  2 H<sub>2</sub>O

==References==
<references/>

== External links ==
* [http://www.inchem.org/documents/icsc/icsc/eics1015.htm International Chemical Safety Card 1015]

{{Authority control}}
[[Category:Acyl chlorides]]
[[Category:Benzene derivatives]]
[[Category:IARC Group 2A carcinogens]]