CAS 78038-42-3

(2S)-2-(4-nitrophenyl)oxirane

Description:

(2S)-2-(4-nitrophenyl)oxirane, also known as a nitrophenyl epoxide, is a chiral organic compound characterized by the presence of an epoxide functional group and a nitrophenyl substituent. The epoxide group, a three-membered cyclic ether, is known for its reactivity, particularly in nucleophilic ring-opening reactions. The presence of the 4-nitrophenyl group enhances the electrophilic nature of the epoxide, making it a useful intermediate in organic synthesis. This compound typically exhibits a solid state at room temperature and is soluble in organic solvents. Its chirality, indicated by the (2S) configuration, suggests that it can exist as enantiomers, which may exhibit different chemical behaviors and biological activities. The nitro group is a strong electron-withdrawing group, influencing the compound's reactivity and stability. Overall, (2S)-2-(4-nitrophenyl)oxirane is significant in synthetic organic chemistry, particularly in the development of pharmaceuticals and agrochemicals.

Formula: C₈H₇NO₃

InChI: InChI=1/C8H7NO3/c10-9(11)7-3-1-6(2-4-7)8-5-12-8/h1-4,8H,5H2/t8-/m1/s1

SMILES: c1cc(ccc1[C@H]1CO1)N(=O)=O

(2S)-2-(4-nitrophenyl)oxirane

CAS: 78038-42-3

Formula: C₈H₇NO₃

Color and Shape: Solid

Molecular weight: 165.1461

Ref: IN-DA008NR5

(S)-(4-Nitrophenyl)oxirane

Controlled Product

CAS: 78038-42-3

Applications (S)-(4-Nitrophenyl)oxirane is used as a reagent in the enantioconvergent synthesis of the β-blocker (R)-Nifenalol which is based on a combined chemoenzymic approach.
References Paedragosa-Moreau, S., et al.: Tetrahedron, 53, 9707 (1997)

Formula: C₈H₇NO₃

Color and Shape: Neat

Molecular weight: 165.146

Ref: TR-N504435