16166-61-3

Basic information

• Product Name: tert-butyl 4-nitrobenzenecarboperoxoate
• CAS NO: 16166-61-3
• Molecular Formula: C₁₁H₁₃NO₅
• Molecular Weight: 239.2246
• Mol File: 16166-61-3.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 379°C at 760 mmHg
• Flash Point: 169.5°C
• Density: 1.226g/cm³
• Vapor Pressure: 6.05E-06mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: tert-butyl 4-nitrobenzenecarboperoxoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-nitrobenzenecarboperoxoate(16166-61-3)
• EPA Substance Registry System: tert-butyl 4-nitrobenzenecarboperoxoate(16166-61-3)

Safety Data

• Hazardous Substances Data: 16166-61-3(Hazardous Substances Data)

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 110-05-4 di-tert-butyl peroxide 
• 555-16-8 4-nitrobenzaldehdye 
• 619-73-8 4-nitrobenzyl chloride 
• 62-23-7 4-nitro-benzoic acid 
• 75-65-0 tert-butyl alcohol 
• 122-04-3 4-nitro-benzoyl chloride 
• 10364-96-2 N-(4-nitrobenzoyl)imidazole 
• 110-86-1 pyridine 

Downstream Products

• 100373-10-2 4-nitro-benzoic acid-(1-propyl-allyl ester) 
• 50457-88-0 Cyclohepten-2-ol-(4-nitro-benzoat) 
• 454183-08-5 (S)-cycloocta-2,6-dien-1-yl 4-nitrobenzoate 
• 200622-05-5 (S)-cyclooct-2-en-1-yl 4-nitrobenzoate 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 212261-68-2 1,2,3,4-tetrahydro-1-naphthyl 4-nitrobenzoate 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 5388-04-5 methylthiomethyl p-nitrobenzoate 

Relevant articles and documents

Highly enantioselective copper-bisoxazoline-catalyzed allylic oxidation of cyclic olefins with tert-butyl p-nitroperbenzoate

Catalytic asymmetric allylic oxidation of cyclic olefins ocurrs for the first time in very high (94-99% ee) enantioselectivity using copper(I) complexes of malonyl derived bisoxazolines and tert-butyl p-nitroperbenzoate giving allyl benzoates in moderate

Immobilization of (l)-valine and (l)-valinol on SBA-15 nanoporous silica and their application as chiral heterogeneous ligands in the Cu-catalyzed asymmetric allylic oxidation of alkenes

SBA-15 nanoporous silica was synthesized by hydrothermal method using P123 surfactant and tetraethoxyortosilicate in acidic condition and then functionalized by 3-chloropropyltrimethoxysilane. Next, by immobilization of chiral amino acid (S)-2-amino-3-methyl butanoic acid (l-valine) and chiral amino alcohol (S)-2-amino-3-methylbutane-1-ol (l-valinol), preparedviathe reduction ofl-valine by NaBH4/I2in THF, on functionalized-SBA-15, chiral heterogeneous ligands AL*-i-Pr-SBA-15 and AA*-i-Pr-SBA-15 were prepared and characterized by FT-IR, XRD, TGA, EDX, SEM, BET-BJH techniques. The asymmetric allylic oxidation of alkenes was done using copper-complexes of these ligands and the as-synthesized peresters. The reactions were optimized by varying various parameters such as temperature, solvent, amount of chiral heterogeneous ligand, as well as the type and amount of copper salt. Under optimized conditions, 6 mg of AL*-i-Pr-SBA-15 and 3.2 mol% of Cu(CH3CN)4PF6in acetonitrile at 50 °C, the chiral allylic ester was obtained with 80% yield and 39% enantiomeric excess in 24 h. The recyclability of the chiral heterogeneous catalysts was also evaluated without significant reduction in the reaction results up to three runs.

2-Aminopyrazine-functionalized MCM-41 nanoporous silica as a new efficient heterogeneous ligand for Cu-catalyzed allylic C–H bonds oxidation of olefins

In spite of the importance of the application of allylic C–H bond oxidation of olefins in organic synthesis and existence of the numerous reports, lots of limitations such as large excess of the olefin respect to the oxidant, low chemical yield, long time of reaction and a large amount of the catalyst were reminded. We introduced a novel catalytic system using functionalized MCM-41 as catalyst support to promote efficiency of this reaction. The heterogeneous ligand Pyr-MCM-41 was prepared by substituted 2-aminopyrazine ligand on functionalized MCM-41 with 3-chloropropyltrimthoxysilane and characterized by FT-IR, XRD, SEM, EDX, BET, TGA, CHN techniques. In situ immobilized Pyr-MCM-41 by copper (I) trifluoromethanesulfonate (CuOTf) was applied in direct catalytic esterification of inert C–H bonds in olefins using various peresters at room temperature.

Designing chiral amido-oxazolines as new chelating ligands devoted to direct Cu-catalyzed oxidation of allylic C–H bonds in cyclic olefins

A new type of amido-oxazoline ligands was conveniently synthesized from inexpensive and commercially available materials in high yields and enantiomeric excesses. The corresponding chiral copper complexes with this class of ligands [C2 symmetric S,S-bis(amido-oxazoline-Cu(II) complex] were synthesized accordingly. The ORTEP diagram of ligand 6a and complex 6a-copper were compared and characterization of the complex confirmed the involvement of both dentate parts of the ligands, the oxygen and nitrogen atoms, in complexation with copper. The utilization of this amido-oxazoline ligands in the copper-catalyzed enantioselective esterification of allylic C–H bonds of cyclic olefins with tert-butyl-4-nitrobenzoperoxoate resulted in the highest activities, yields (up to 95%) and enantioselectivities (up to 96%) in the presence of HZSM-5 zeolite. These new findings highlight the protocol as one of the most attractive and useful methods for the oxidation of the asymmetric allylic C–H bond of cycloalkenes compared to other methodologies reported in the literature.