3585-88-4

Basic information

• Product Name: N-TERT-BUTYL-ALPHA-(4-NITROPHENYL)NITRONE
• Synonyms: N-TERT-BUTYL-ALPHA-(4-NITROPHENYL)NITRONE;n-tert-butyl-α-(4-nitrophenyl)nitrone;2-Methyl-N-[(4-nitrophenyl)methylene]-2-propanamineN-oxide;N-(4-Nitrobenzylidene)-1,1-dimethylethanamine N-oxide;N-(4-Nitrobenzylidene)-tert-butylamine N-oxide;N-tert-Butyl-4-nitrobenzenemethanimine N-oxide;N-tert-Butyl-4-nitrophenylmethanimine N-oxide
• CAS NO: 3585-88-4
• Molecular Formula: C₁₁H₁₄N₂O₃
• Molecular Weight: 222.24
• Product Categories: B;Stains and Dyes;Stains&Dyes, A to
• Mol File: 3585-88-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 147-149 °C(lit.)
• Boiling Point: 363.42°C (rough estimate)
• Flash Point: 170.1 °C
• Appearance: /
• Density: 1.1990 (rough estimate)
• Vapor Pressure: 3.51E-05mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• CAS DataBase Reference: N-TERT-BUTYL-ALPHA-(4-NITROPHENYL)NITRONE(CAS DataBase Reference)
• NIST Chemistry Reference: N-TERT-BUTYL-ALPHA-(4-NITROPHENYL)NITRONE(3585-88-4)
• EPA Substance Registry System: N-TERT-BUTYL-ALPHA-(4-NITROPHENYL)NITRONE(3585-88-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3585-88-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 2646, 1992 DOI: 10.1021/jo00035a020

InChI:InChI=1/C11H14N2O3/c1-11(2,3)12(14)8-9-4-6-10(7-5-9)13(15)16/h4-8H,1-3H3/b12-8+

Upstream product

• 16649-50-6 N-tert-Butylhydroxylamine 
• 555-16-8 4-nitrobenzaldehdye 
• 59862-75-8 (E)-2-methyl-N-(4-nitrophenylmethylene)propan-2-amine 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 
• 917-95-3 t-butylnitrite 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 718-36-5 (p-nitrobenzylidene)(tert-butyl)amine 
• 3489-67-6 N-(t-butyl)-N-p-nitrobenzylamine 
• 75-18-3 dimethylsulfide 
• 75-64-9 tert-butylamine 
• 26378-36-9 2-tert-butyl-3-(4-nitrophenyl)-1,2-oxaziridine 

Downstream Products

• 135485-67-5 C₁₈H₁₉N₂O₅ 
• 63710-80-5 C₁₇H₁₉N₂O₃ 
• 26378-36-9 2-tert-butyl-3-(4-nitrophenyl)-1,2-oxaziridine 
• 555-16-8 4-nitrobenzaldehdye 
• 137578-02-0 C₁₁H₁₅N₂O₄ 
• 52884-61-4 C₁₁H₁₅N₂O₃ 
• 53544-99-3 p-Nitrobenzoyl-tert-butylnitroxid 

Relevant articles and documents

Single-Step Approach toward Nitrones via Pyridinium Ylides: The DMAP-Catalyzed Reaction of Benzyl Halides with Nitrosoarenes

A single-step approach is reported for the preparation of nitrones from benzyl halides and nitrosoarenes via pyridinium ylides, utilizing 4-dimethylaminopyridine (DMAP) catalyst and mild reaction conditions (Li2CO3, dimethylacetamide, and room temperature). The reaction provides both keto-and aldonitrones in high yields with a wide scope for benzyl halides and nitrosoarenes. In the same reaction system, 2-methyl-2-nitrosopropane, which does not have an aryl group, also affords the corresponding N-tert-butyl nitrones from primary benzyl bromides that have an electron-withdrawing group. As an application of the reaction, methyl 2-bromo-2-phenylacetate was used to prepare the corresponding isoxazolidine by a sequential one-pot synthesis.

Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines

Microwave irradiation allows increasing the speed of several reactions and also offers the possibility of eliminating poisoning organic solvents. In this work we report the microwave-assisted neat synthesis of α-phenyl-tert-butylnitrone (PBN) and other alkyl and aryl nitrones and also the rapid synthesis of isoxazolidines resulting from 1,3-dipolar cycloaddition of nitrones to ethyl trans-crotonate.

A novel route to substituted 4-methylene-4,5-dihydroisoxazoles mediated by hafnium(IV) chloride

Heating alkyl vinyl ketones and N-tert-butylarylmethylide-neamine N-oxides in the presence of HfCl4 results in the formation of 4-methylene-4,5-dihydroisoxazoles in good yield.