3,5-Dinitrocatechol

Base Information

• Chemical Name: 3,5-Dinitrocatechol
• CAS No.: 7659-29-2
• Molecular Formula: C6H4N2O6
• Molecular Weight: 200.108
• European Community (EC) Number: 642-347-6
• UNII: VK0VA22GY2
• DSSTox Substance ID: DTXSID00227391
• Nikkaji Number: J227.993B
• Wikidata: Q223026
• Pharos Ligand ID: J4UFRQ3753F8
• Metabolomics Workbench ID: 146714
• ChEMBL ID: CHEMBL168276
• Mol file: 7659-29-2.mol

Synonyms:3,5-dinitrocatechol;3,5-dinitropyrocatechol;OR 486;OR-486;OR486;Ro 01-2812;Ro 12812

Chemical Property of 3,5-Dinitrocatechol

Chemical Property:

• Vapor Pressure: 1.64E-05mmHg at 25°C
• Melting Point: 166-166.5℃
• Boiling Point: 354.5°C at 760 mmHg
• Flash Point: 162.2°C
• PSA: 132.10000
• Density: 1.819g/cm3
• LogP: 1.96060
• Storage Temp.: 2-8°C
• Solubility.: H2O: 0.17 mg/mL Solutions may be stored for several days at
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 200.00693585
• Heavy Atom Count: 14
• Complexity: 246

Purity/Quality:

> 95% ^*data from raw suppliers

OR-486 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1[N+](=O)[O-])O)O)[N+](=O)[O-]
• General Description: 3,5-Dinitrocatechol is identified as a product formed during the photochemical reactions of picramide and NN-dimethylpicramide in alkaline aqueous sodium hydroxide solutions, alongside 2,6-dinitroquinone and nitrite ions. Its formation occurs under visible light exposure, indicating its role as a secondary product in the decomposition or transformation of these aromatic nitro-compounds in alkaline conditions. No further details about its properties or reactivity are provided in the abstract.

Technology Process of 3,5-Dinitrocatechol

There total 12 articles about 3,5-Dinitrocatechol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2,4-dinitro-6-pentafluorophenyliodoniophenolate (89563-21-3) → 3,5-dinitrocatechol (7659-29-2)

Guidance literature:

With sodium hydroxide; In methanol; for 2h;

Reference yield: 35.0%

2,4-dinitro-6-phenyliodonium phenolate (89563-18-8) → 3,5-dinitrocatechol (7659-29-2)

Guidance literature:

With sodium hydroxide; In methanol; for 2h;

Reference yield:

dinoseb (88-85-7) → 3,5-dinitrosalicylaldehyde (2460-59-5) + 1,2-dihydroxy-4-nitrobenzene (3316-09-4) + 3,5-dinitrocatechol (7659-29-2)

Guidance literature:

With TiO₂ nanoparticles loaded on silica-alumina aerogels from industrial fly ash; In water; at 40 - 280 ℃; for 5h; pH=4.86; Reagent/catalyst; Concentration; Kinetics; UV-irradiation;

DOI:10.1016/S1872-2067(16)62546-9

upstream raw materials:

2-methoxy-4,6-dinitrophenol

dimethyl phthalate

2,4-dinitro-6-pentafluorophenyliodoniophenolate

2,4-dinitro-6-phenyliodonium phenolate

Downstream raw materials:

5,7-Diacetamido-benzdioxan-(1,4)

2-(2-hydroxy-3,5-dinitro-phenoxy)-ethanol

1,2-dipropionyloxy-3,5-dinitrobenzene

1,2-diacetoxy-3,5-dinitro-benzene

Refernces

Reactions of Aromatic Nitro-compounds in Alkaline Media. Part VIII. Behaviour of Picramide and NN-Dimethylpicramide in Aqueous Sodium Hydroxide

10.1039/jr9640001727

The study investigates the reactions of aromatic nitro-compounds, specifically picramide (PicNH?) and its NN-dimethyl derivative (PicNMe?), in aqueous sodium hydroxide solutions. Picramide and dimethylpicramide both react with hydroxide ions to form soluble complexes. Picramide forms a 1:1 complex with hydroxide ions, while dimethylpicramide forms a 1:2 complex. The equilibrium constants for these reactions were measured. The study also examines the kinetics of the reactions, including the slow, irreversible hydrolysis that leads to the formation of picrate ions. In the presence of visible light, additional reactions occur, resulting in the formation of nitrite ions and a mixture of 3,5-dinitrocatechol and 2,6-dinitroquinone. The rates of these reactions were measured as a function of hydroxide ion concentration. The study aims to understand the behavior of these compounds in alkaline media and the nature of the complexes formed.