Benzoin
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| Benzoin | |
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2-hydroxy-1,2-di(phenyl)ethanone |
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Other names
2-hydroxy-2-phenylacetophenone, 2-hydroxy-1,2-diphenylethanone, desyl alcohol, bitter almond oil camphor |
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| Identifiers | |
| CAS number | 119-53-9  |
| PubChem | 8400 |
| ChemSpider | 8093 |
| UNII | L7J6A1NE81 |
| KEGG | C01408 |
| ChEBI | CHEBI:17682 |
| ChEMBL | CHEMBL190677 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C14H12O2 |
| Molar mass | 212.24 g mol−1 |
| Appearance | off-white crystals |
| Density | 1.31 g/cm3 |
| Melting point |
132–137 °C |
| Boiling point |
344 °C |
| Solubility in water | Slightly Soluble |
| Solubility in Chlorine | Soluble |
| Hazards | |
| NFPA 704 |
 1
2
0
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 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Benzoin (pron.: or ) 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.
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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.[1] The catalytic synthesis by the benzoin condensation was improved by Nikolay Zinin during his time with Liebig.[2][3]
Uses
The main uses of benzoin are as a precursor to benzil, which is a photoinitiator.[4] The conversion proceeds by organic oxidation using copper(II),[5] nitric acid, or oxone. In one study, this reaction is carried out with atmospheric oxygen and basic alumina in dichloromethane.[6]
References
- ^ Wöhler, Liebig; Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie 3 (3): 249–282. doi:10.1002/jlac.18320030302.
- ^ N. Zinin (1839). "Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe". Annalen der Pharmacie 31 (3): 329–332. doi:10.1002/jlac.18390310312.
- ^ N. Zinin (1840). "Ueber einige Zersetzungsprodukte des Bittermandelöls". Annalen der Pharmacie 34 (2): 186–192. doi:10.1002/jlac.18400340205.
- ^ 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
- ^ Clarke, H. T.; Dreger.E. E. (1941), "Benzil", Org. Synth.; Coll. Vol. 1: 87
- ^ Konstantinos Skobridis, Vassiliki Theodorou, Edwin Weber (2006). "A very simple and chemoselective air oxidation of benzoins to benzils using alumina". Arkivoc. 06-1798JP: 102–106.
External links
- Benzoin synthesis, Organic Syntheses, Coll. Vol. 1, p.94 (1941); Vol. 1, p.33 (1921)
