Styrene oxide

Styrene oxide
Names
	Preferred IUPAC name Phenyloxirane
	Other names Epoxystyrene; Styryl oxide; Phenylethylene oxide
Identifiers
CAS Number	96-09-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	108582
ChEBI	CHEBI:17907 ;
ChemSpider	7005;
ECHA InfoCard	100.002.252
EC Number	202-476-7;
Gmelin Reference	50213
KEGG	C02083 ;
PubChem CID	7276;
RTECS number	CZ9625000;
UNII	9QH06NGT6O ;
UN number	2810 3082
CompTox Dashboard (EPA)	DTXSID2021286 ;
	InChI InChI=1S/C8H8O/c1-2-4-7(5-3-1)8-6-9-8/h1-5,8H,6H2 Key: AWMVMTVKBNGEAK-UHFFFAOYSA-N;
	SMILES c1ccccc1C2CO2;
Properties
Chemical formula	C8H8O
Molar mass	120.151 g·mol−1
Appearance	Colorless to light yellow liquid
Density	1.052 g/mL
Melting point	−37 °C (−35 °F; 236 K)
Boiling point	194 °C (381 °F; 467 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H312, H319, H350
Precautionary statements	P201, P202, P264, P280, P281, P302+P352, P305+P351+P338, P308+P313, P312, P322, P337+P313, P363, P405, P501
Safety data sheet (SDS)	Oxford University MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Styrene oxide is an epoxide derived from styrene. It can be prepared by epoxidation of styrene with peroxybenzoic acid, in the Prilezhaev reaction:^[1]

Styrene oxide is slightly soluble in water. A trace amount of acid in water causes hydrolysis to racemic phenylethyleneglycol via a benzylic cation. If the amount of water is not sufficient, acid-catalyzed isomerization for phenylacetaldehyde will occur.^[2]

Styrene oxide in the body is metabolized to mandelic acid, phenylglyoxylic acid, benzoic acid and hippuric acid.

Hydrogenation of styrene oxide affords phenethyl alcohol.^[3]

^ Harold Hibbert and Pauline Burt (1941). "Styrene Oxide". Organic Syntheses; Collected Volumes, vol. 1, p. 494.
^ Verfahren zur Herstellung von Phenylacetaldehyde, BASF-Patent DE3546372A1 vom 2. Juli 1987
^ Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141. ISBN 978-3-527-30673-2.

[1] Harold Hibbert and Pauline Burt (1941). "Styrene Oxide". Organic Syntheses; Collected Volumes, vol. 1, p. 494.

[2] Verfahren zur Herstellung von Phenylacetaldehyde, BASF-Patent DE3546372A1 vom 2. Juli 1987

[3] Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141. ISBN 978-3-527-30673-2.

[1]

[2]

[3]