6388-74-5

Basic information

• Product Name: (p-nitrophenyl)oxirane
• Synonyms: (p-nitrophenyl)oxirane;4-nitrostyrene oxide;(4-Nitrophenyl)oxirane;1-(Oxiranyl)-4-nitrobenzene;1-Nitro-4-oxiranylbenzene;4-Nitrophenyloxirane;1-(Epoxyethyl)-4-nitrobenzene;1,2-Epoxy-1-(p-nitrophenyl)ethane
• CAS NO: 6388-74-5
• Molecular Formula: C₈H₇NO₃
• Molecular Weight: 165.14608
• EINECS: 228-998-5
• Mol File: 6388-74-5.mol
• Article Data: 106

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: (p-nitrophenyl)oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: (p-nitrophenyl)oxirane(6388-74-5)
• EPA Substance Registry System: (p-nitrophenyl)oxirane(6388-74-5)

Safety Data

• Hazardous Substances Data: 6388-74-5(Hazardous Substances Data)

Usage

Description

(p-nitrophenyl)oxirane, also known as p-nitrophenyl epoxide, is a chemical compound characterized by the molecular formula C9H7NO3. It is a pale yellow solid at room temperature, highly reactive due to its epoxide functionality, and is commonly used as a reagent in organic synthesis. Its primary applications include the formation of chiral auxiliaries and serving as a precursor to various other compounds. Given its sensitivity to moisture and air, it is typically handled and stored under inert gas conditions. Additionally, (p-nitrophenyl)oxirane is recognized for its potential mutagenic and toxic properties, necessitating adherence to proper handling procedures and safety precautions.

Uses

Used in Organic Synthesis:
(p-nitrophenyl)oxirane is used as a reagent in organic synthesis for its high reactivity, particularly in the formation of chiral auxiliaries. These auxiliaries are essential in asymmetric synthesis, where they help to control the stereochemistry of the reaction, leading to the selective formation of desired enantiomers.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (p-nitrophenyl)oxirane is utilized as a precursor to various compounds that have potential therapeutic applications. Its ability to form chiral auxiliaries is particularly valuable in the development of enantiomerically pure drugs, which can have significant implications for the efficacy and safety of medications.
Used in Chemical Research:
(p-nitrophenyl)oxirane is also used in chemical research as a model compound to study the reactivity and selectivity of epoxides. Its properties and reactions provide insights into the mechanisms of epoxide opening and the factors that influence the stereochemistry of the resulting products.
Safety Precautions:
Due to its potential mutagenic and toxic properties, (p-nitrophenyl)oxirane requires careful handling and storage. It should be kept away from moisture and air, and handled under inert gas conditions to prevent decomposition and potential health hazards. Users should follow proper safety procedures, including the use of personal protective equipment, to minimize exposure and ensure a safe working environment.

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

Upstream product

• 1073-67-2 4-vinylbenzyl chloride 
• 100-13-0 4-nitrostyrene 
• 99-81-0 4-Nitrophenacyl bromide 
• 19922-82-8 2-bromo-1-(4-nitrophenyl)ethanol 
• 13407-16-4 α-(chloromethyl)-4-nitrobenzyl alcohol 
• 6388-74-5 p-Nitrophenyloxirane 
• 536-74-3 phenylacetylene 
• 623-47-2 propynoic acid ethyl ester 
• 502934-29-4 (R)-1-(4-nitrophenyl)-2-(p-tolylsulfonyloxy)ethanol 
• 325856-49-3 (R)-2-chloro-1-(4-nitrophenyl)ethanol 
• 125653-67-0 (R)-(-)-2-bromo-1-(4-nitrophenyl)ethanol 
• 77977-74-3 (R)-(-)-1-(4-nitrophenyl)-1,2-ethanediol 
• 555-16-8 4-nitrobenzaldehdye 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 92868-81-0 2-(2-hydroxy-2-(4-nitro-phenyl)-ethyl)-isoindole-1,3-dione 
• 52090-00-3 1-[2-hydroxy-2-(4-nitro-phenyl)-ethyl]-pyridinium 
• 41959-09-5 2-methoxy-2-(4-nitrophenyl)ethanol 
• 147159-79-3 2-Methoxy-1-(4-nitro-phenyl)-ethanol 
• 97302-72-2 2-Cyclohexylamino-1-(4-nitro-phenyl)-ethanol; hydrochloride 
• 136247-26-2 α-<2-amino>ethyl>-p-nitrobenzyl alcohol 
• 116351-49-6 α-<methyl>-4-nitrobenzyl alcohol 
• 61192-64-1 N-methyl-2-hydroxy-2-(4'-nitrophenyl)ethylamine 
• 100-02-7 4-nitro-phenol 
• 40460-44-4 glycolaldehyde hydrate 
• 15873-56-0 monochloroacetaldehyde hydrate 
• 100-27-6 2-(4-nitrophenyl)ethanol 
• 6531-13-1 1-[4-nitrophenyl]-1-ethanol 
• 1460-05-5 p-nitrophenylacetaldehyde 

Relevant articles and documents

SUBSTITUTED PYRAZOLE COMPOUNDS AS TOLL RECEPTOR INHIBITORS

Disclosed are compounds of Formula (I) N-oxides, or salts thereof, wherein G, A, R1, and R5 are defined herein. Also disclosed are methods of using such compounds as inhibitors of signaling through Toll-like receptor 7, or 8, or 9, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating inflammatory and autoimmune diseases.

Effect of the Ligand Backbone on the Reactivity and Mechanistic Paradigm of Non-Heme Iron(IV)-Oxo during Olefin Epoxidation

The oxygen atom transfer (OAT) reactivity of the non-heme [FeIV(2PyN2Q)(O)]2+ (2) containing the sterically bulky quinoline-pyridine pentadentate ligand (2PyN2Q) has been thoroughly studied with different olefins. The ferryl-oxo complex 2 shows excellent OAT reactivity during epoxidations. The steric encumbrance and electronic effect of the ligand influence the mechanistic shuttle between OAT pathway I and isomerization pathway II (during the reaction stereo pure olefins), resulting in a mixture of cis-trans epoxide products. In contrast, the sterically less hindered and electronically different [FeIV(N4Py)(O)]2+ (1) provides only cis-stilbene epoxide. A Hammett study suggests the role of dominant inductive electronic along with minor resonance effect during electron transfer from olefin to 2 in the rate-limiting step. Additionally, a computational study supports the involvement of stepwise pathways during olefin epoxidation. The ferryl bend due to the bulkier ligand incorporation leads to destabilization of both (Formula presented.) and (Formula presented.) orbitals, leading to a very small quintet–triplet gap and enhanced reactivity for 2 compared to 1. Thus, the present study unveils the role of steric and electronic effects of the ligand towards mechanistic modification during olefin epoxidation.

Tandem transfer hydrogenation-epoxidation of ketone substrates catalysed by alkene-tethered Ru(ii)-NHC complexes

A series of nine cyclopentadienyl Ru(ii)-NHC complexes (1-9) have been synthesised by systematically varying the ligand and/or ligand substituents: η5-C5H4R′ (R′ = H, Me), EPh3 (E = P, As), NHC (Im, BIm), where NHC = Im(R)(R′) (R, R′ = Me, Bn, 4-NO2Bn, C2H4Ph, C4H7). Each of the Ru(ii)-NHC complexes features an N-alkenyl tether to attain bidentate NHC ligands. All complexes found application as catalysts in the tandem transfer hydrogenation and epoxidation reactions of carbonyl substrates. The catalytic activity of the complexes was shown to be similar, with efficiencies of up to 69% conversion after 18 hours and varying alcohol:epoxide selectivity for a variety of electronically diverse carbonyl substrates. Complex 3, with a nitro-containing substituent on the NHC ligand, was the only complex that showed preference for the alcohol product over the epoxide after 18 hours of reaction time.