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 ;
3D model (JSmol)	Interactive image; Interactive image;
3DMet	B00286;
Beilstein Reference	391839
ChEBI	CHEBI:17682 ;
ChEMBL	ChEMBL190677 ;
ChemSpider	8093 ;
KEGG	C01408 ;
PubChem CID	8400;
RTECS number	DI1590000;
UNII	L7J6A1NE81 ;
	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 Key: ISAOCJYIOMOJEB-UHFFFAOYSA-N ; 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)
Melting point	135 to 139 °C (275 to 282 °F; 408 to 412 K)
Boiling point	330 to 356 °C (626 to 673 °F; 603 to 629 K)
Solubility in water	Slightly soluble
Solubility in ethanol	Very good
Solubility in ether	Slightly soluble
Solubility in chlorine	Soluble
Solubility in chloroform	Very good
Hazards
GHS hazard statements	H412
GHS precautionary statements	P273, P501
NFPA 704 (fire diamond)	1 1 0
	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).
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	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.

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

↑ ^1.0 ^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.
↑ 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. https://zenodo.org/record/1426941. Retrieved 2020-09-10.
↑ 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.
↑ 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
↑ 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.
↑ Clarke, H. T.; Dreger.E. E. (1941). "Benzil". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv1p0087. ; Collective Volume, 1, pp. 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. http://www.arkat-usa.org/ark/journal/2006/I10_General/1798/06-1798JP%20as%20published%20mainmanuscript.asp. ^{[yes|permanent dead link|dead link}}]}
↑ 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.
↑ 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.
↑ U.S. Patent 2,242,775
↑ 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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Original source: https://en.wikipedia.org/wiki/Benzoin (organic compound). Read more

[crc97-1] 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.

[Ullmann-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%20as%20published%20mainmanuscript.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

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