Benzoin (organic compound)
{{distinguish|Benzoin (resin)}}{{other|Benzoin (disambiguation)}}
{{Chembox
| Name = Benzoin
| Watchedfields = changed
| verifiedrevid = 464186825
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Benzoin.svg
| ImageFile1 = Benzoin-3D-balls.png
| PIN = 2-Hydroxy-1,2-diphenylethan-1-one
| OtherNames = 2-Hydroxy-2-phenylacetophenone
2-Hydroxy-1,2-diphenylethanone
Desyl alcohol
Bitter almond oil camphor
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8093
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L7J6A1NE81
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01408
| InChI = 1/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H
| InChIKey = ISAOCJYIOMOJEB-UHFFFAOYAO
| SMILES1 = c1ccc(cc1)C(C(=O)c2ccccc2)O
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 190677
| Beilstein = 391839
| 3DMet = B00286
| RTECS = DI1590000
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ISAOCJYIOMOJEB-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 119-53-9
| PubChem = 8400
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17682
| SMILES = O=C(c1ccccc1)C(O)c2ccccc2
}}
|Section2={{Chembox Properties
| C=14 | H=12 | O=2
| Appearance = Off-white crystals
| Density = 1.310 g/cm3 (20 °C){{cite book | author=William M. Haynes | title=CRC Handbook of Chemistry and Physics | edition=97th | year=2016 | publisher=CRC Press | location=Boca Raton | isbn=978-1-4987-5429-3 | page=3-40 | url=https://books.google.com/books?id=VVezDAAAQBAJ}}
| MeltingPt_notes =
| BoilingPt_notes =
| Solubility = Slightly soluble
| Solvent1 = ethanol
| Solvent2 = ether
| Solubility2 = Slightly soluble
| Solvent3 = chlorine
| Solubility3 = Soluble
| Solvent4 = chloroform
}}
|Section3={{Chembox Hazards
| LD50 = 10.000 mg/kg
| MainHazards =
| FlashPt =
| AutoignitionPt =
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
| NFPA-S =
| HPhrases = {{H-phrases|412}}
| PPhrases = {{P-phrases|273|501}}
}}
}}
Benzoin ({{IPAc-en|ˈ|b|ɛ|n|z|oʊ|.|ᵻ|n}} or {{IPAc-en|-|ɔɪ|n}}) is an organic compound with the formula PhCH(OH)C(O)Ph. It is a hydroxy ketone attached to two phenyl groups. It appears as off-white crystals, with a light camphor-like odor. Benzoin is synthesized from benzaldehyde in the benzoin condensation. It is chiral and it exists as a pair of enantiomers: (R)-benzoin and (S)-benzoin.
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 reported in 1832 by Justus von Liebig and Friedrich Woehler during their research on oil of bitter almond, which is benzaldehyde with traces of hydrocyanic acid.{{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
| last2 = Liebig | hdl = 2027/hvd.hxdg3f
| hdl-access = free
}} The catalytic synthesis by the benzoin condensation was improved by Nikolay Zinin during his time with Liebig.{{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 = https://zenodo.org/record/1426941
| doi = 10.1002/jlac.18390310312
| access-date = 2020-09-10
| archive-date = 2022-07-09
| archive-url = https://web.archive.org/web/20220709093441/https://zenodo.org/record/1426941
| url-status = live
| title = Ueber einige Zersetzungsprodukte des Bittermandelöls
| author = N. Zinin
| journal = Annalen der Pharmacie
| volume = 34
| issue = 2
| pages = 186–192
| year = 1840
| url = https://zenodo.org/record/1426951
| doi = 10.1002/jlac.18400340205
| access-date = 2019-06-30
| archive-date = 2022-07-09
| archive-url = https://web.archive.org/web/20220709093441/https://zenodo.org/record/1426951
| url-status = live
}}
Uses
The main use of benzoin is as a precursor to benzil, which is used as a photoinitiator.Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, 2002 by Wiley-VCH, Wienheim. {{doi|10.1002/14356007.a15_077}}{{Cite book |last=Nakamura |first=Kenichiro |url=https://www.worldcat.org/oclc/884012539 |title=Photopolymers : photoresist materials, processes, and applications |date=2015 |isbn=978-1-4665-1731-8 |location=Boca Raton, FL |oclc=884012539}} The conversion proceeds by organic oxidation using copper(II),{{OrgSynth | author = Clarke, H. T. |author2=Dreger.E. E. | title = Benzil | collvol = 1 | collvolpages = 87 | year = 1941 | prep = cv1p0087}} nitric acid, or oxone. In one study, this reaction is carried out with atmospheric oxygen and basic alumina in dichloromethane.{{cite journal|title=A very simple and chemoselective air oxidation of benzoins to benzils using alumina|author1=Konstantinos Skobridis|author2=Vassiliki Theodorou|author3=Edwin Weber|journal=Arkivoc|volume=06-1798JP|pages=102–106|year=2006|url=http://www.arkat-usa.org/ark/journal/2006/I10_General/1798/06-1798JP%20as%20published%20mainmanuscript.asp}}{{Dead link|date=June 2019 |bot=InternetArchiveBot |fix-attempted=yes }}
Benzoin also sees wide spread use in powder coating formulations, where it acts as a degassing agent during the curing stage. This action prevents surface defects such as 'pinholing'.{{cite journal |last1=Maxwell |first1=B.E |last2=Wilson |first2=R.C |last3=Taylor |first3=H.A |last4=Williams |first4=D.E |last5=Farnham |first5=W |last6=Tria |first6=J |title=Understanding benzoin's mode of action in powder coatings |journal=Progress in Organic Coatings |date=November 2001 |volume=43 |issue=1–3 |pages=158–166 |doi=10.1016/S0300-9440(01)00181-3}}{{cite journal |last1=Jahromi |first1=Shahab |last2=Mostert |first2=Ben |last3=Derks |first3=Andreas |last4=Koldijk |first4=Fokelien |title=Mechanism of action of benzoin as a degassing agent in powder coatings |journal=Progress in Organic Coatings |date=December 2003 |volume=48 |issue=2–4 |pages=183–193 |doi=10.1016/S0300-9440(03)00096-1}}
Benzoin can be used in the preparation of several pharmaceutical drugs including oxaprozin, ditazole, and phenytoin.{{US patent|2242775}}
Preparation
Benzoin is prepared from benzaldehyde via the benzoin condensation.
{{
OrgSynth
| author = Roger Adams
| author2 = C. S. Marvel
| title = Benzoin
| volume = 1
| pages = 33
| year = 1921
| collvol = 1
| collvolpages = 94
| collyear = 1941
| prep = CV1P0094
}}
References
{{reflist}}
External links
- [https://web.archive.org/web/20120905010547/http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0094 Benzoin synthesis], Organic Syntheses, Coll. Vol. 1, p. 94 (1941); Vol. 1, p. 33 (1921)
{{Authority control}}