586-11-8

Basic information

• Product Name: 3,5-DINITROPHENOL
• Synonyms: 3,5-Dinitrofenol;3,5-dinitro-pheno;AKOS BB-9367;3,5-DINITROPHENOL;PHENOL, 3,5-DINITRO-;TIMTEC-BB SBB009900
• CAS NO: 586-11-8
• Molecular Formula: C₆H₄N₂O₅
• Molecular Weight: 184.11
• Mol File: 586-11-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 125.1°C
• Boiling Point: 318.03°C (rough estimate)
• Flash Point: 157.2°C
• Appearance: /
• Density: 1.7020
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4738 (estimate)
• PKA: pK1:6.732 (25°C)
• Water Solubility: 13.42g/L(51.6 oC)
• CAS DataBase Reference: 3,5-DINITROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DINITROPHENOL(586-11-8)
• EPA Substance Registry System: 3,5-DINITROPHENOL(586-11-8)

Safety Data

• RIDADR: 1320
• HazardClass: 4.1
• PackingGroup: I
• Hazardous Substances Data: 586-11-8(Hazardous Substances Data)

Usage

Description

3,5-DINITROPHENOL is an organic compound that exists as colorless monoclinic prisms. It is characterized by its flammability and solubility in various organic solvents such as ethanol, ether, chloroform, and benzene.

Uses

Used in Chemical Synthesis:
3,5-DINITROPHENOL is used as a chemical intermediate for the synthesis of various compounds, including pharmaceuticals, dyes, and other organic chemicals. Its reactivity and solubility in organic solvents make it a versatile building block in the chemical industry.
Used in Energy Production:
3,5-DINITROPHENOL has been historically used as a component in the production of energy, specifically in the context of enhancing the efficiency of certain processes. However, due to its potential hazards and environmental concerns, its use in this application has been largely discontinued.
Used in Analytical Chemistry:
3,5-DINITROPHENOL is employed as a reagent in analytical chemistry for the detection and quantification of various substances, such as sugars and amino acids, through colorimetric assays. Its ability to form colored complexes with specific compounds makes it a valuable tool in research and quality control.
Used in Environmental Applications:
3,5-DINITROPHENOL can be utilized in environmental applications, such as the detection and monitoring of water quality. Its reactivity with certain pollutants allows for the development of sensitive and selective methods to assess contamination levels in aquatic systems.

InChI:InChI=1/C6H6N2O6/c9-6(10)2-4(7(11)12)1-5(3-6)8(13)14/h1-2,9-10H,3H2

Upstream product

• 99-35-4 1,3,5-trinitrobenzene 
• 767-00-0 4-cyanophenol 
• 163685-00-5 2-(3,5-Dinitro-phenoxy)-4,6-dimethoxy-[1,3,5]triazine 
• 110-91-8 morpholine 
• 7446-70-0 aluminium trichloride 
• 5327-44-6 3,5-dinitroanisole 
• 618-87-1 3, 5-dinitroaniline 
• 80824-77-7 4'-(benzyloxy)benzanilide 
• 731772-53-5 5-acetoxy-2-acetylamino-1,3-dinitrobenzene 
• 107-29-9 Acetaldehyde oxime 
• 7664-93-9 sulfuric acid 
• 32654-60-7 4-amino-3,5-dinitrophenol 
• 215776-08-2 3,5-dinitrophenyl β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-3)-β-β-D-glucopyranoside 
• 1122-58-3 dmap 

Downstream Products

• 618-64-4 3-Amino-5-nitro-phenol 
• 4328-17-0 trinitrophloroglucinol 
• 116296-08-3 acetic acid-(3-hydroxy-5-nitro-anilide) 
• 116995-44-9 2,4,6-tribromo-3,5-dinitro-phenol 
• 322765-69-5 Pentanitro-phenol 
• 15925-97-0 3,5-Dinitrophenyl-dimethylcarbamat 
• 52427-05-1 2-bromo-5-nitrophenol 
• 20734-70-7 5-nitroresorcinol 
• 55065-94-6 N-(4-bromo-3-hydroxyphenyl)acetamide 
• 116632-23-6 3-bromo-5-nitro-phenol 
• 55120-56-4 4-bromo-3-hydroxy-aniline 
• 860209-11-6 3-amino-2-bromo-5-nitro-phenol 
• 860767-41-5 3-amino-2,4,6-tribromo-5-nitro-phenol 
• 626-46-0 2,6-diamino-4-pyrimidinone 

Relevant articles and documents

A convenient synthesis of phenols

Anilines are rapidly, often within 60 minutes, converted into the corresponding phenols in up to 87% isolated yield. The presented experimentally simple protocol display broad compatibility with a variety of functional groups, and in particular, well suited for the preparation of methyl-substituted phenols. Such phenols are not easily available by other synthetic approaches. The formation of phenolic radical coupling products was not observed even for activated anilines using this open flask method.

Ethyl acetate as a pro-reducing agent in an one-pot reductive deamination of nitroanilines

The reductive deamination of various nitro-substituted anilines by the new method (20% H2SO4/NaNO2/ethyl acetate, Method 1) was studied and compared that with a similar procedure previously developed by Pare et al. (i.e., concentrated H2SO4/NaNO2/ethanol, Method 2) for the dediazonization of 4-methyl-2,6-dinitroaniline. The deaminated products derived from the mononitro-substituted anilines were obtained in good-to-high yield by Method 1 depending upon the position of the nitro group to the amino function. The higher yield of the de-aminated products was observed from the substituted meta-nitroanilines. Method 1 was more suitable for the deamination of 3-nitroanilines. Method 2 was more favorable for the de-amination of denitro-substituted anilines than that for the mononitroanilines. Ethyl acetate was more suitable for the reductive deamination of mononitroanilines, while ethanol was more appropriate for dinitroanilines.

Substitution for a nitro group in 1,3,5-trinitrobenzene and meta-substituted 1,3-dinitrobenzenes under the action of oximes

The title reaction was performed with 1,3,5-trinitrobenzene and 1-X-3,5-dinitrobenzenes (X = CF3, ArO) in the presence of K2CO3in N-methylpyrrolidone or DMF solutions to form O-3,5-dinitrophenyl oximes or O-3-X-5-nitrophenyl oximes, respectively.