Benzoin (organic compound)

Benzoin

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

CAS Number

* 119-53-9 Y

3D model (JSmol)

* Interactive image
* Interactive image

3DMet  |

* B00286

Beilstein Reference

| 391839
ChEBI |

* CHEBI:17682 Y

ChEMBL |

* ChEMBL190677 Y

ChemSpider |

* 8093 Y

KEGG |

* C01408 Y

PubChem CID

* 8400

RTECS number |

* DI1590000

UNII |

* L7J6A1NE81 Y

InChI

* InChI=1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H Y

Key: ISAOCJYIOMOJEB-UHFFFAOYSA-N Y

* 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

Key: ISAOCJYIOMOJEB-UHFFFAOYAO

SMILES

* O=C(c1ccccc1)C(O)c2ccccc2

* c1ccc(cc1)C(C(=O)c2ccccc2)O

Properties

Chemical formula

| C14H12O2
Molar mass | 212.248 g·mol−1
Appearance  | Off-white crystals
Density | 1.310 g/cm3 (20 °C)[1]
Melting point |  135 to 139[1] °C (275 to 282 °F; 408 to 412 K)
Boiling point |  330 to 356[1] °C (626 to 673 °F; 603 to 629 K)

Solubility in water

| Slightly soluble
Solubility in ethanol | Very good[1]
Solubility in ether | Slightly soluble
Solubility in chlorine | Soluble
Solubility in chloroform | Very good[1]
Hazards

GHS hazard statements

| H412

GHS precautionary statements

| P273, P501
NFPA 704 (fire diamond)  |

Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 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 YN ?)
Infobox references

Benzoin (/ˈbɛnzoʊ.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.

## Contents

* 1 History
* 2 Uses
* 3 Preparation
* 4 References
* 5 External links

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

## Uses

The main use of benzoin is as a precursor to benzil, which is used as a photoinitiator.[5][6] The conversion proceeds by organic oxidation using copper(II),[7] nitric acid, or oxone. In one study, this reaction is carried out with atmospheric oxygen and basic alumina in dichloromethane.[8]

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'.[9][10]

Benzoin can be used in the preparation of several pharmaceutical drugs including oxaprozin, ditazole, and phenytoin.[11]

## Preparation

Benzoin is prepared from benzaldehyde via the benzoin condensation.[12]

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. p. 3-40. ISBN 978-1-4987-5429-3. https://books.google.com/books?id=VVezDAAAQBAJ.
2. ↑ Wöhler, Liebig; Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie 3 (3): 249–282. doi:10.1002/jlac.18320030302.
3. ↑ N. Zinin (1839). "Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe". Annalen der Pharmacie 31 (3): 329–332. doi:10.1002/jlac.18390310312. https://zenodo.org/record/1426941. Retrieved 2020-09-10.
4. ↑ N. Zinin (1840). "Ueber einige Zersetzungsprodukte des Bittermandelöls". Annalen der Pharmacie 34 (2): 186–192. doi:10.1002/jlac.18400340205. https://zenodo.org/record/1426951. Retrieved 2019-06-30.
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. ↑ Nakamura, Kenichiro (2015). Photopolymers : photoresist materials, processes, and applications. Boca Raton, FL. ISBN 978-1-4665-1731-8. OCLC 884012539. https://www.worldcat.org/oclc/884012539.
7. ↑ Clarke, H. T.; Dreger.E. E. (1941). "Benzil". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv1p0087. ;  Collective Volume, 1, pp. 87
8. ↑ 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 as published mainmanuscript.asp. [yes|permanent dead link|dead link}}]
9. ↑ Maxwell, B.E; Wilson, R.C; Taylor, H.A; Williams, D.E; Farnham, W; Tria, J (November 2001). "Understanding benzoin's mode of action in powder coatings". Progress in Organic Coatings 43 (1–3): 158–166. doi:10.1016/S0300-9440(01)00181-3.
10. ↑ Jahromi, Shahab; Mostert, Ben; Derks, Andreas; Koldijk, Fokelien (December 2003). "Mechanism of action of benzoin as a degassing agent in powder coatings". Progress in Organic Coatings 48 (2–4): 183–193. doi:10.1016/S0300-9440(03)00096-1.
11. ↑ U.S. Patent 2,242,775
12. ↑ Roger Adams; C. S. Marvel (1921). "Benzoin". Organic Syntheses 1: 33. http://www.orgsyn.org/demo.aspx?prep=CV1P0094. ;  Collective Volume, 1, 1941, pp. 94

## External links

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

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*[CID]: Compound ID
*[H412]: Harmful to aquatic life with long lasting effects
*[P273]: Avoid release to the environment
*[P501]: Dispose of contents/container to …