Benzoin (organic compound)

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Benzoin
Benzoin.svg
Benzoin-3D-balls.png
Names
Preferred IUPAC name
2-Hydroxy-1,2-diphenylethan-1-one
Other names
2-Hydroxy-2-phenylacetophenone
2-Hydroxy-1,2-diphenylethanone
Desyl alcohol
Bitter almond oil camphor
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.938
KEGG
UNII
Properties
C14H12O2
Molar mass 212.248 g·mol−1
Appearance Off-white crystals
Density 1.31 g/cm3
Melting point 134 to 138 °C (273 to 280 °F; 407 to 411 K)
Boiling point 344 °C (651 °F; 617 K)
Slightly soluble
Solubility in ethanol Slightly soluble
Solubility in alcohol Soluble
Solubility in ether Slightly soluble
Solubility in chlorine Soluble
Hazards
R-phrases (outdated) R36/38 [1]
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Lethal dose or concentration (LD, LC):
10.000 mg/kg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☑Y verify (what is ☑Y☒N ?)
Infobox references

Benzoin (/ˈbɛnz.ɪn/ or /-ɔɪn/) 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[edit]

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.[2] The catalytic synthesis by the benzoin condensation was improved by Nikolay Zinin during his time with Liebig.[3][4]

Uses[edit]

The main uses of benzoin are as a precursor to benzil, which is a photoinitiator.[5] The conversion proceeds by organic oxidation using copper(II),[6] nitric acid, or oxone. In one study, this reaction is carried out with atmospheric oxygen and basic alumina in dichloromethane.[7]

Benzoin can be used in the preparation of several pharmaceutical drugs including oxaprozin, ditazole, and phenytoin.[8]

Preparation[edit]

Benzoin is prepared from benzaldehyde via the benzoin condensation.[9]

References[edit]

  1. ^ "Benzoin" (PDF). FischerSci. FischerSci.
  2. ^ Wöhler, Liebig; Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie. 3 (3): 249–282. doi:10.1002/jlac.18320030302. hdl:2027/hvd.hxdg3f.
  3. ^ N. Zinin (1839). "Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe". Annalen der Pharmacie. 31 (3): 329–332. doi:10.1002/jlac.18390310312.
  4. ^ N. Zinin (1840). "Ueber einige Zersetzungsprodukte des Bittermandelöls". Annalen der Pharmacie. 34 (2): 186–192. doi:10.1002/jlac.18400340205.
  5. ^ 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
  6. ^ Clarke, H. T.; Dreger.E. E. (1941). "Benzil". Organic Syntheses.; Collective Volume, 1, p. 87
  7. ^ 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.[permanent dead link]
  8. ^ U.S. Patent 2,242,775
  9. ^ Clarke, H. T.; Dreger.E. E. (1941). "Benzil". Organic Syntheses.; Collective Volume, 1, p. 87

External links[edit]

  • Benzoin synthesis, Organic Syntheses, Coll. Vol. 1, p. 94 (1941); Vol. 1, p. 33 (1921)