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. Its chemical formula is C₆H₅C₂H₃O. It can be prepared by epoxidation of styrene with peroxybenzoic acid, in the Prilezhaev reaction:

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.

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

Hydrogenation of styrene oxide affords phenethyl alcohol.