Benzoin 1969188 216892756 2008-06-03T18:19:58Z 198.102.159.141 {{Chembox new | ImageFile = Benzoin.png | ImageFile1 = Benzoin-3D-balls.png | IUPACName = | OtherNames = | Section1 = {{Chembox Identifiers | CASNo = 119-53-9 | PubChem = | SMILES = O=C(c2ccccc2)C(O)c1ccccc1 }} | Section2 = {{Chembox Properties | Formula = C<sub>14</sub>H<sub>12</sub>O<sub>2</sub> | MolarMass = 212.25 g/mol | Appearance = | Density = 1.31 g/cm<sup>3</sup> | MeltingPt = 137 &deg;C | BoilingPt = 344 &deg;C | Solubility = Slightly Soluble | Solvent = [[ethanol]] | SolubleOther = Slightly Soluble | Solvent = [[alcohol]] | SolubleOther = Soluble | Solvent = [[ether]] | SolubleOther = Slightly Soluble | Solvent = [[Chlorine]] | SolubleOther = Soluble }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | Autoignition = }} }} :''"Benzoin" is also used to describe [[benzoin resin]], which does not contain the benzoin described on this page.'' '''Benzoin''' or '''2-Hydroxy-2-phenylacetophenone''' or '''2-Hydroxy-1,2-Diphenylethanone ''' or '''desyl alcohol''' or '''bitter almond oil camphor''' is an [[organic compound]] consisting of an ethylene bridge flanked by [[phenyl]] groups and with a [[hydroxyl]] and a [[ketone]] [[functional group]]. It comes as off-white crystals, with a light [[camphor]] odor. Benzoin is synthesized from [[benzaldehyde]] in the [[benzoin condensation]]. Its main uses are: * [[photocatalyst]] in [[photopolymerization]] and a [[photoinitiator]] * raw material for [[benzil]] by [[organic oxidation]] with [[nitric acid]] or [[oxone]]. In one study,<ref>{{cite journal|title=A very simple and chemoselective air oxidation of benzoins to benzils using alumina| author=Konstantinos Skobridis, Vassiliki Theodorou, Edwin Weber| journal=[[Arkivoc]] |volume=06-1798JP|pages=102–106| date=2006| url=http://www.arkat-usa.org/ark/journal/2006/I10_General/1798/06-1798JP%20as%20published%20mainmanuscript.asp}}</ref> this reaction is carried out with atmospheric oxygen and basic [[alumina]] in [[dichloromethane]]. Benzoin is '''not''' a constituent of [[benzoin resin]] obtained from the [[benzoin tree]] (Styrax) or [[tincture of benzoin]]. The main component in these natural products is [[benzoic acid]]. ==History== Benzoin was first synthesized in 1832 by [[Justus von Liebig]] and [[Friedrich Woehler]] during the research on [[bitter almond oil]], which was [[benzaldehyde]] with traces of [[hydrocyanic acid]].<ref>{{cite journal | title = Untersuchungen über das Radikal der Benzoesäure | author = Wöhler, Liebig | journal = Annalen der Pharmacie | volume = 3 | issue = 3 | pages = 249–282 | year = 1832 | url = | doi = 10.1002/jlac.18320030302 }}</ref> The catalytic synthesis by the [[benzoin condensation]] was improved by the research of [[Nikolay Zinin]] during his time with Liebig. <ref>{{cite journal | title = Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe | author = N. Zinin | journal = Annalen der Pharmacie | volume = 31 | issue = 3 | pages = 329–332 | year = 1839 | url = | doi = 10.1002/jlac.18390310312 }}</ref><ref>{{cite journal | title = Ueber einige Zersetzungsprodukte des Bittermandelöls | author = N. Zinin | journal = Annalen der Pharmacie | volume = 34 | issue = 2 | pages = 186–192 | year = 1840 | url = | doi = 10.1002/jlac.18400340205 }}</ref> ==References== {{reflist}} *[http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0094 Synthesis] [[Category:alcohols]] [[Category:ketones]] [[Category:Aromatic compounds]] [[Category:Arabic words and phrases]] [[ar:بنزوين]] [[de:Benzoe]] [[es:Benzoína]] [[fr:Benjoin]] [[ja:ベンゾイン]] [[pl:Benzoina]] [[vi:Benzoin]] [[zh:安息香]]