943-39-5

Basic information

• Product Name: 4-nitroperoxybenzoic acid
• Synonyms: p-Nitroperbenzoic acid;4-nitroperoxybenzoic acid;4-nitroperbenzoic acid
• CAS NO: 943-39-5
• Molecular Formula: C₇H₅NO₅
• Molecular Weight: 183.1183
• EINECS: 213-401-2
• Mol File: 943-39-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 138°C
• Boiling Point: 316.77°C (rough estimate)
• Flash Point: 184.5°C
• Appearance: /
• Density: 1.6074 (rough estimate)
• Vapor Pressure: 1.69E-06mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• PKA: 6.71±0.40(Predicted)
• CAS DataBase Reference: 4-nitroperoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitroperoxybenzoic acid(943-39-5)
• EPA Substance Registry System: 4-nitroperoxybenzoic acid(943-39-5)

Safety Data

• Hazardous Substances Data: 943-39-5(Hazardous Substances Data)

Usage

Production Methods

This peroxide can be prepared from p-nitrobenzoic acid and 90% hydrogen peroxide in methanesulfonic acid medium.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 1336, 1962 DOI: 10.1021/jo01051a050Synthetic Communications, 18, p. 2123, 1988 DOI: 10.1080/00397918808068282

InChI:InChI=1/C7H5NO5/c9-7(13-12)5-1-3-6(4-2-5)8(10)11/h1-4,12H

Upstream product

• 122-04-3 4-nitro-benzoyl chloride 
• 62-23-7 4-nitro-benzoic acid 
• 15024-11-0 4-methylphenyl 4-nitrobenzoate 
• 103413-89-4 Dichlorethyl-p-nitrobenzoat 
• 21105-92-0 trimethyl-[β-(4-nitro-benzoyloxy)-ethyl]-ammonium 
• 24935-47-5 4-(4-nitro-benzoyloxy)-benzoic acid 
• 72511-60-5 4-Nitrobenzoesaeure-(2,2,2-trifluorethylester) 
• 22775-46-8 4-Nitro-benzoic acid 2-fluoro-ethyl ester 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 1712-84-1 p-nitrobenzoyl peroxide 
• 141-52-6 sodium ethanolate 
• 29913-02-8 p-Nitrobenzoyldiethylphosphat 

Downstream Products

• 286-20-4 cyclohexane-1,2-epoxide 
• 1829-89-6 p-methoxybenzoyl p-nitrobenzoyl peroxide 
• 13137-24-1 benzyl-4-nitrobenzoic carbonic anhydride 
• 34195-70-5 1-(S(O)C₆H₅)-2-(S(O)C₆H₅)-1.2-C₂B₁₀H₁₀ 
• 1433900-71-0 C₂₆H₂₅NO₉ 
• 34313-07-0 1.12-(SO₂C₆H₅)2-1.12-C₂B₁₀H₁₀ 
• 34313-08-1 1-(S(O)-m-CB₁₀H₁₀CH)-2-(C₆H₅)-1.2-C₂B₁₀H₁₀ 
• 108535-08-6 Mn(IV)(O)(OH)(tetramesitylporphyrin) 
• 104619-71-8 ((C₄H₂N)C(C₆H₂)(CH₃)3)4FeOOCO(C₆H₄)NO₂ 
• 76077-77-5 ClMn(IV)(O)(tetraphenylporphyrin) 
• 62-23-7 4-nitro-benzoic acid 
• 148353-27-9 C₂₀H₈N₄(C₆H₃(CH₃)2)4Fe(OOCOC₆H₄NO₂) 
• 29200-05-3 4-(4-nitro-benzoyloxymethyl)-3-phenyl-3H-oxazol-2-one 
• 29200-04-2 4-hydroxy-4-(4-nitro-benzoyloxymethyl)-3-phenyl-oxazolidin-2-one 

Relevant articles and documents

Highly Energetic, Low Sensitivity Aromatic Peroxy Acids

The synthesis, structure, and energetic materials properties of a series of aromatic peroxy acid compounds are described. Benzene-1,3,5-tris(carboperoxoic) acid is a highly sensitive primary energetic material, with impact and friction sensitivities similar to those of triacetone triperoxide. By contrast, benzene-1,4-bis(carboperoxoic) acid, 4-nitrobenzoperoxoic acid, and 3,5-dinitrobenzoperoxoic acid are much less sensitive, with impact and friction sensitivities close to those of the secondary energetic material 2,4,6-trinitrotoluene. Additionally, the calculated detonation velocities of 3,5-dinitrobenzoperoxoic acid and 2,4,6-trinitrobenzoperoxoic acid exceed that of 2,4,6-trinitrotoluene. The solid-state structure of 3,5-dinitrobenzoperoxoic acid contains intermolecular O-H?O hydrogen bonds and numerous N?O, C?O, and O?O close contacts. These attractive lattice interactions may account for the less sensitive nature of 3,5-dinitrobenzoperoxoic acid.

Predominant role of basicity of leaving group in α-effect for nucleophilic ester cleavage

It has been found that α-effects in nucleophilic reactions, unexpectedly large nucleophilicity due to adjacent unpaired electrons, are strongly dependent on the structure of substrate. The nucleophilic cleavages of 4-nitrobenzoate esters and 4-methylbenzo