Benzoin

Benzoin: Benzoin

IUPAC name

2-hydroxy-1,2-di(phenyl)ethanone

Other names

2-hydroxy-2-phenylacetophenone, 2-hydroxy-1,2-diphenylethanone, desyl alcohol, bitter almond oil camphor

Identifiers

CAS number 119-53-9^Y

PubChem 8400

ChemSpider 8093^Y

UNII L7J6A1NE81^Y

KEGG C01408^Y

ChEBI CHEBI:17682^Y

ChEMBL CHEMBL190677^Y

Jmol-3D images Image 1
Image 2

SMILES

O=C(c1ccccc1)C(O)c2ccccc2
c1ccc(cc1)C(C(=O)c2ccccc2)O

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

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

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Benzoin (pronounced /ˈbɛnzoʊ.ɨn, -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 References

4 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.^[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 with, copper(II), nitric acid, or oxone.^[5] 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., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0087 ; 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. http://www.arkat-usa.org/ark/journal/2006/I10_General/1798/06-1798JP%20as%20published%20mainmanuscript.asp.

External links

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

Categories:
Alcohols
Arabic words and phrases
Aromatic ketones

Benzoin


IUPAC name 2-hydroxy-1,2-di(phenyl)ethanone
Other names 2-hydroxy-2-phenylacetophenone, 2-hydroxy-1,2-diphenylethanone, desyl alcohol, bitter almond oil camphor
Identifiers
CAS number	119-53-9^Y
PubChem	8400
ChemSpider	8093^Y
UNII	L7J6A1NE81^Y
KEGG	C01408^Y
ChEBI	CHEBI:17682^Y
ChEMBL	CHEMBL190677^Y
Jmol-3D images	Image 1 Image 2
SMILES O=C(c1ccccc1)C(O)c2ccccc2 c1ccc(cc1)C(C(=O)c2ccccc2)O
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
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Synonyms:

Gumbenjamin, benjamin, friar's balsam

Look at other dictionaries:

Benzoin — Ben*zoin (b[e^]n*zoin ), n. [Cf. F. benjoin, Sp. benjui, Pg. beijoin; all fr. Ar. lub[=a]n j[=a]w[=i] incense form Sumatra (named Java in Arabic), the first syllable being lost. Cf. {Benjamin}.] Note: [Called also {benjamin}.] 1. A resinous… … The Collaborative International Dictionary of English
benzoin — balsamic resin obtained from a tree (Styrax benzoin) of Indonesia, 1560s (earlier as bengewine, 1550s), from M.Fr. benjoin (16c.), which comes via Spanish, Portuguese, or Italian from Arabic luban jawi incense of Java (actually Sumatra, with… … Etymology dictionary
Benzoin — Benzoin, Benzol u. Benzon, s.u. Benzoyl B) … Pierer's Universal-Lexikon
Benzoīn — Benzoīn, Baum, s. Styrax … Meyers Großes Konversations-Lexikon
benzoin — [ben′zō in΄, ben zō′in; ben′zoin΄] n. [Fr benjoin < It benzoino < Ar lubān jāwī, incense of Java: lu dropped because falsely assumed to be the article] 1. a balsamic resin obtained from certain tropical Asiatic trees (genus Styrax of the… … English World dictionary
Benzoin — Strukturformel Allgemeines Name Benzoin Andere Namen 2 Hy … Deutsch Wikipedia
benzoin — benzoin1 /ben zoh in, zoyn, ben zoh in/, n. 1. Also called gum benjamin, gum benzoin. a reddish brown, aromatic balsamic resin occurring in almondlike fragments and having a vanillalike odor, obtained from trees of the genus Styrax, esp. S.… … Universalium
Benzoin — Ben|zo|in [zu ↑ Benzoe], das; s, e: Syn.: 2 Hydroxy 1,2 diphenylethanon: ein ↑ Acyloin, das natürlicherweise im Benzoeharz (Benzoin) vorkommt oder durch Benzoin Addition (früher: B. Kondensation, vgl. Acyloin Addition) herzustellen ist. * * *… … Universal-Lexikon
benzoin — benzoinis stirakas statusas T sritis vardynas apibrėžtis Stirakinių šeimos prieskoninis, vaistinis augalas (Styrax benzoin), paplitęs atogrąžų Azijoje. Iš jo gaunami lipai, eterinis aliejus ir derva. atitikmenys: lot. Styrax benzoin angl.… … Lithuanian dictionary (lietuvių žodynas)
benzoin — A balsamic resin obtained from Styrax b. (family Styracaceae), used as a stimulant expectorant, but usually by inhalation in laryngitis and bronchitis; it retards rancidification of fats and is used for this purpose in the official benzoinated… … Medical dictionary

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Benzoin

Contents

History

Uses

References

External links

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Benzoin

Contents

History

Uses

References

External links

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