S4921
trans-Stilbene oxide
98%
Synonym(s):
trans-1,2-Diphenyloxirane
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About This Item
Empirical Formula (Hill Notation):
C14H12O
CAS Number:
Molecular Weight:
196.24
Beilstein/REAXYS Number:
82740
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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assay
98%
mp
65-67 °C (lit.)
SMILES string
O1[C@@H]([C@H]1c2ccccc2)c3ccccc3
InChI
1S/C14H12O/c1-3-7-11(8-4-1)13-14(15-13)12-9-5-2-6-10-12/h1-10,13-14H/t13-,14-/m1/s1
InChI key
ARCJQKUWGAZPFX-ZIAGYGMSSA-N
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General description
Trans-stilbene oxide also known as trans-1,2-Diphenyloxirane, is often used in photochemistry, whereit can change its structure when exposed to light.Stilbene oxides can break apart when they are excited bylight, leading to the formation of carbonyl ylides. It is also commonlyused to produce trans-stilbene sulfides.
Application
- Chiral Stationary Phases for Liquid Chromatography: Trans-stilbene oxide has been utilized in the fabrication of cellulose derivative-coated spherical covalent organic frameworks, serving as chiral stationary phases for high-performance liquid chromatographic enantioseparation, demonstrating its pivotal role in advanced analytical methodologies (Yan et al., 2022).
- Method Selection for Chiral High-Performance Liquid Chromatography: Its application extends to the utilization of hysteresis phenomena for chiral high-performance liquid chromatographic method selection in polar organic mode, enhancing the efficiency and specificity of pharmaceutical compound analysis (Horváth et al., 2020).
- Adsorption Properties for Enantioseparations: The effect of chiral selector loading on the adsorption properties of fully- and superficially-porous particles is crucial for high-efficient ultrafast enantioseparations, where trans-stilbene oxide derivatives play a significant role (Felletti et al., 2018).
- Catalysis in Alkene Epoxidation: Trans-stilbene oxide is involved in innovative catalysis research, specifically in the development of carbon nitride-supported Fe(2) cluster catalysts for alkene epoxidation, showcasing its utility in sustainable chemical synthesis (Tian et al., 2018).
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Photochemistry of cis-and trans-stilbene oxides
Lee, George A
The Journal of Organic Chemistry, 41, 2656-2658 (1976)
V J Mayani et al.
Chirality, 21(2), 255-261 (2008-06-19)
Chromatographic behavior of nonracemic mixtures, viz., mandelic acid and stilbene oxide as analytes has been studied in detailed by enantiomer self-disproportionation on achiral ordered mesoporous material M41S and regular silica gel as stationary phases. Enantiomer self-disproportionation gave enhanced separation of
Li-Ming Yang et al.
Bioorganic & medicinal chemistry letters, 12(7), 1013-1015 (2002-03-23)
A new series of trans-stilbene benzenesulfonamide derivatives were designed and synthesized as potential antitumor agents. These new compounds were evaluated in the National Cancer Institute's 60 human tumor cell line in vitro screen. Compounds 9-13 were cytotoxic against several cell
Rujin Gong et al.
Journal of chromatography. A, 1286, 119-126 (2013-03-19)
The chromatographic enantioseparation of trans-stilbene oxide (TSO) was studied experimentally and theoretically, where the preparative column was packed with 20 μm Chiralcel OD stationary phase and hexanes/2-propanol were used as mobile phase. The bed porosity, axial dispersion coefficient, mass transfer
Larry Miller et al.
Journal of chromatography. A, 1250, 256-263 (2012-06-26)
Preparative supercritical fluid chromatography (SFC) has become the preferred method for the rapid purification of drug candidates during the pharmaceutical discovery process. This paper will discuss the evaluation of injection techniques for preparative SFC. A thorough evaluation of mixed stream
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