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| Benzoin | |
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| Identifiers | |
| CAS number | 119-53-9 |
| SMILES |
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| Properties | |
| Molecular formula | C14H12O2 |
| Molar mass | 212.24 g mol−1 |
| Density | 1.31 g/cm3 |
| Melting point |
137 °C |
| Boiling point |
344 °C |
| Solubility in water | Slightly Soluble |
| Solubility in Chlorine | Soluble |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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- "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,1 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 their research on oil of bitter almond, which is benzaldehyde with traces of hydrocyanic acid.2 The catalytic synthesis by the benzoin condensation was improved by the research of Nikolay Zinin during his time with Liebig. 34
References
- ^ 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, http://www.arkat-usa.org/ark/journal/2006/I10_General/1798/06-1798JP%20as%20published%20mainmanuscript.asp.
- ^ Wöhler, Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie 3 (3): 249–282. doi:.
- ^ N. Zinin (1839). "Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe". Annalen der Pharmacie 31 (3): 329–332. doi:.
- ^ N. Zinin (1840). "Ueber einige Zersetzungsprodukte des Bittermandelöls". Annalen der Pharmacie 34 (2): 186–192. doi:.
Wikipedia content modification information:
- This page was last modified on 8 October 2008, at 20:57.
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