78038-42-3

Basic information

• Product Name: (S)-2-(4-NITROPHENYL)OXIRANE
• Synonyms: (S)-2-(4-NITROPHENYL)OXIRANE;(s)-4-nitrostyrene oxide;(2S)-2β-(4-Nitrophenyl)oxirane;(S)-(4-Nitrophenyl)oxirane;(S)-p-Nitrostyrene oxide
• CAS NO: 78038-42-3
• Molecular Formula: C₈H₇NO₃
• Molecular Weight: 165.14608
• Mol File: 78038-42-3.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 302.7°C at 760 mmHg
• Flash Point: 158°C
• Appearance: /
• Density: 1.372g/cm³
• Vapor Pressure: 0.00175mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: (S)-2-(4-NITROPHENYL)OXIRANE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(4-NITROPHENYL)OXIRANE(78038-42-3)
• EPA Substance Registry System: (S)-2-(4-NITROPHENYL)OXIRANE(78038-42-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 78038-42-3(Hazardous Substances Data)

Usage

Description

(S)-2-(4-NITROPHENYL)OXIRANE, also known as (S)-(4-Nitrophenyl)oxirane, is an organic compound that plays a significant role in the field of organic synthesis. It is characterized by its unique structure, which includes a nitrophenyl group attached to an oxirane ring. (S)-2-(4-NITROPHENYL)OXIRANE is known for its reactivity and selectivity, making it a valuable building block in the synthesis of various pharmaceuticals and other organic compounds.

Uses

Used in Pharmaceutical Industry:
(S)-2-(4-NITROPHENYL)OXIRANE is used as a reagent in the enantioconvergent synthesis of the β-blocker (R)-Nifenalol. This synthesis is based on a combined chemoenzymic approach, which allows for the selective production of the desired enantiomer with high efficiency and selectivity. The use of (S)-2-(4-NITROPHENYL)OXIRANE in this process is crucial for obtaining the desired chiral center in the final product, which is essential for the biological activity and therapeutic effects of the β-blocker.
In addition to its application in the synthesis of (R)-Nifenalol, (S)-2-(4-NITROPHENYL)OXIRANE can also be used as a reagent in the synthesis of other chiral compounds with potential pharmaceutical applications. Its unique reactivity and selectivity make it a valuable tool for chemists working on the development of new drugs and therapeutic agents.
Furthermore, (S)-2-(4-NITROPHENYL)OXIRANE can be employed in other industries that require the synthesis of chiral compounds, such as the agrochemical, fragrance, and flavor industries. Its ability to provide enantioselective synthesis routes can help in the development of more effective and environmentally friendly products in these fields.

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

Upstream product

• 125653-67-0 (R)-(-)-2-bromo-1-(4-nitrophenyl)ethanol 
• 19922-82-8 2-bromo-1-(4-nitrophenyl)ethanol 
• 6388-74-5 p-Nitrophenyloxirane 
• 536-74-3 phenylacetylene 
• 623-47-2 propynoic acid ethyl ester 
• 99-81-0 4-Nitrophenacyl bromide 
• 100-13-0 4-nitrostyrene 
• 34006-49-0 2-chloro-1-(4-nitrophenyl)ethanone 
• 502934-29-4 (R)-1-(4-nitrophenyl)-2-(p-tolylsulfonyloxy)ethanol 
• 325856-49-3 (R)-2-chloro-1-(4-nitrophenyl)ethanol 
• 77977-74-3 (R)-(-)-1-(4-nitrophenyl)-1,2-ethanediol 
• 166239-06-1 (S)-(+)-2-bromo-1-(4-nitrophenyl)ethanol 
• 357952-87-5 (S)-(+)-1-(4-Nitrophenyl)-2-(p-tolylsulfonyloxy)ethanol 
• 216160-44-0 (S)-2-chloro-1-(4-nitrophenyl)ethanol 

Downstream Products

• 5054-57-9 (-)-Nifenalol 
• 77977-74-3 (S)-(+)-1-(4-nitrophenyl)-1,2-ethanediol 
• 1312566-14-5 (S)-3-(2-hydroxy-2-(4-nitrophenyl)ethylamino)propan-1-ol 
• 1312564-98-9 (S)-N-(4-(1,4-oxazepan-2-yl)phenyl)-3-chlorobenzamide hydrochloride 
• 397869-61-3 (S)-2-azido-1-(4-nitrophenyl)ethan-1-ol 
• 5302-36-3 (+)-Nifenalol 
• 1312566-19-0 (S)-tert-butyl 2-(4-(3-chlorobenzamido)phenyl)-1,4-oxazepane-4-carboxylate 
• 1312566-18-9 (S)-tert-butyl 2-(4-aminophenyl)-1,4-oxazepane-4-carboxylate 
• 1312566-17-8 (S)-tert-butyl 2-(4-nitrophenyl)-1,4-oxazepane-4-carboxylate 
• 1312566-16-7 (S)-tert-butyl (2-hydroxy-2-(4-nitrophenyl)ethyl)(3-hydroxypropyl)carbamate 
• 1304788-12-2 C₁₄H₁₃NO₄ 
• 166239-06-1 (S)-(+)-2-bromo-1-(4-nitrophenyl)ethanol 
• 77977-74-3 (R)-(-)-1-(4-nitrophenyl)-1,2-ethanediol 
• 325856-49-3 (R)-2-chloro-1-(4-nitrophenyl)ethanol 

Relevant articles and documents

Biomimetic non-heme iron-catalyzed epoxidation of challenging terminal alkenes using aqueous H2O2 as an environmentally friendly oxidant

Catalysis mediated by iron complexes is emerging as an eco-friendly and inexpensive option in comparison to traditional metal catalysis. The epoxidation of alkenes constitutes an attractive application of iron(III) catalysis, in which terminal olefins are challenging substrates. Herein, we describe our study on the design of biomimetic non-heme ligands for the in situ generation of iron(III) complexes and their evaluation as potential catalysts in epoxidation of terminal olefins. Since it is well-known that active sites of oxidases might involve imidazole fragment of histidine, various simple imidazole derivatives (seven compounds) were initially evaluated in order to find the best reaction conditions and to develop, subsequently, more elaborated amino acid-derived peptide-like chiral ligands (10 derivatives) for enantioselective epoxidations.

Multistep Organic Transformations over Base-Rhodium/Diamine-Bifunctionalized Mesostructured Silica Nanoparticles

The assembly of multiple catalytic functionalities within a single mesoporous silica as a catalyst for multistep enantioselective organic transformations in an environmentally friendly medium is a significant challenge in heterogeneous asymmetric catalysis. Herein, we took advantage of a BF4 ? anion hydrogen bonding strategy to anchor a chiral cationic rhodium/diamine complex within base-functionalized mesostructured silica nanoparticles conveniently to construct a bifunctional heterogeneous catalyst. The solid-state 13C NMR spectrum discloses the well-defined chiral Rh/diamine active species, and we used XRD, N2 adsorption–desorption, and electron microscopy to reveal the ordered mesostructure. The combination of bifunctionality in the silica nanoparticles enables two kinds of efficient enantioselective organic transformations with high yields and enantioselectivities, in which the asymmetric transfer hydrogenation of α-haloketones followed by epoxidation provides various chiral aryloxiranes, and the amination of α-haloketones with anilines followed by asymmetric transfer hydrogenation produces various β-amino alcohols. Furthermore, the catalyst can be recovered and recycled for seven times without a loss of catalytic activity, which is an attractive feature for multistep organic transformations in a sustainable benign process.

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.