16600-92-3

Basic information

• Product Name: 2-NITROPHLOROGLUCINOL
• Synonyms: 2-NITROBENZENE-1,3,5-TRIOL;2-NITROPHLOROGLUCINOL;1-NITROPHLOROGLUCINOL;2,4,6-TRIHYDROXYNITROBENZENE;1,3,5-TRIHYDROXY-2-NITROBENZENE;NITROPHLOROGLUCINOL;1-nitro-2,4,6-trihydroxybenzene;2-Nitro-1,3,5-benzenetriol
• CAS NO: 16600-92-3
• Molecular Formula: C₆H₅NO₅
• Molecular Weight: 171.11
• EINECS: 240-656-7
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Organic Building Blocks;Oxygen Compounds;Polyols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 16600-92-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 189-193 °C(lit.)
• Boiling Point: 343 °C at 760 mmHg
• Flash Point: 159.7 °C
• Appearance: /
• Density: 1.771 g/cm³
• Vapor Pressure: 3.64E-05mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.92±0.20(Predicted)
• BRN: 1963331
• CAS DataBase Reference: 2-NITROPHLOROGLUCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROPHLOROGLUCINOL(16600-92-3)
• EPA Substance Registry System: 2-NITROPHLOROGLUCINOL(16600-92-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 16600-92-3(Hazardous Substances Data)

Usage

Description

2-Nitrophloro-glucinol, also known as 4-hydroxy-3-nitrobenzaldehyde, is an organic compound that serves as a versatile synthetic intermediate in the chemical industry. It is characterized by its nitro group and hydroxyl group attached to a benzene ring, which allows for various chemical reactions and transformations.

Uses

Used in Pharmaceutical Industry:
2-Nitrophloro-glucinol is used as a synthetic intermediate for the preparation of benzoxazoles and benzothiazoles. These compounds are selective ligands for the human beta-estrogen receptor (ER-β), which makes them valuable in the development of pharmaceuticals targeting hormone-related conditions and diseases.
Used in Chemical Synthesis:
In the chemical synthesis industry, 2-Nitrophloro-glucinol is utilized as a key building block for the creation of various complex organic molecules. Its reactivity and functional groups enable it to participate in a wide range of chemical reactions, such as condensation, substitution, and reduction, leading to the formation of diverse chemical products.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 2-Nitrophloro-glucinol is also employed in research and development laboratories. It is used to study the mechanisms of various chemical reactions and to develop new synthetic methods and strategies for the preparation of novel compounds with potential applications in different fields, such as pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C6H5NO5/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2,8-10H/p-3

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 67-56-1 methanol 
• 10135-18-9 diethyl 2,4,6-trihydroxyisophthalate 
• 63458-87-7 2,4,6-trihydroxy-5-nitro-isophthalic acid diethyl ester 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 480-66-0 2,4,6-trihydroxyacetophenone 

Downstream Products

• 139173-32-3 aminophloroglucinol 
• 14227-18-0 1,3,5-trimethoxy-2-nitrobenzene 
• 127-17-3 2-oxo-propionic acid 
• 1332507-55-7 3-(3',5'-di-O-tert-butyl-dimethyl-silane-d-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-O-pivaloyl-2-oxophenoxadine 
• 1332507-69-3 3-(2'-deoxy-D-ribofuranosyl)-9-(2-N-benzylcarbamylethoxy)-1,3-diaza-7-O-pivaloyl-2-oxophenoxadine 
• 1332507-67-1 N-[4-(2-N-benzylcarbamylethoxy-4,6-dihydroxyphenyl)]-2'-deoxy-5-bromouridine 
• 1332507-66-0 N-[4-(2-N-benzylcarbamylethoxy-6-hydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine 
• 1332507-65-9 3',5'-di-O-acetyl-N-[4-(2-N-benzylcarbamyl-ethoxy-6-hydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine 
• 1332507-64-8 3',5'-di-O-acetyl-N-[4-(2,6-dihydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine 

Related news

Statistical optimization of the enzymatic breakdown of 2-NITROPHLOROGLUCINOL (cas 16600-92-3) using thermo tolerant mixed Intracellular enzymes from Serratia marcescens08/14/2019

Serratia marcescens, capable of degrading 2-Nitrophloroglucinol (NPG), an endocrine disruptor, was isolated from the soil contaminated with tannery wastewater. The mixed intracellular enzymes (MICE) from S. marcescens were extracted and characterized. The activity of MICE was found to be the max...detailed

Relevant articles and documents

Sequential nitration/hydrogenation protocol for the synthesis of triaminophloroglucinol: Safe generation and use of an explosive intermediate under continuous-flow conditions

A continuous-flow process for the synthesis of triaminophloroglucinol has been developed. The synthetic procedure is based on a sequential nitration/reduction protocol which uses phloroglucinol as an inexpensive substrate. During the initial exothermic nitration step employing a combination of ammonium nitrate and sulfuric acid, the temperature was controlled through the enhanced heat transfer derived from the high surface-to-volume ratio of the utilized capillary tubing. Clogging of the tubing due to precipitation of trinitrophloroglucinol (TNPG) was avoided by immersing the tubular reactor in an ultrasound bath during the process. The nitration mixture was diluted with water and immediately subjected to catalytic hydrogenation of the nitro groups using a commercially available continuous-flow reactor and PtO2 as heterogeneous catalyst, thus avoiding the isolation of the highly unstable and explosive TNPG intermediate.

Optimization of fluorescence property of the 8-oxodGclamp derivative for better selectivity for 8-oxo-2′-deoxyguanosine

2′-Deoxyguanosine (dG) suffers from oxidation by reactive oxygen species (ROS) to form 8-oxo-2′-deoxyguanosine (8-oxo-dG), which is regarded as a marker of oxidative stress in the cells. In our continuous study for the recognition molecule of 8-oxo-dG, 8-oxoGclamp and its derivatives have been identified as the selective fluorescent probe. However, it is an obstacle for further application that dG also forms a complex with 8-oxoGclamp, resulting in fluorescence quenching in less polar solvents. Quenching of the fluorescence of 8-oxoGclamp is thought to involve photo-induced electron transfer in the complex. It was hypothesized that the energy level of the excited state of 8-oxoGclamp and the HOMO energy of dG are the preliminary determinant of the quenching efficiency. Thus, fluorescence properties of the substituted derivatives at the 7-position of the 1,3-diazaphenoxazine part of 8-oxoGclamp were investigated. Among the new derivatives, fluorescence of the 7-phenyl substituted 8-oxoGclamp was not quenched by dG even in the stable complex, exhibiting the highest selectivity for 8-oxo-dG.

Novel Method for Nitration and Polymerisation of Symmetric Trihydroxybenzene Using Ceric(IV) Ammonium Nitrate

Only symmetric isomer of trihydroxybenzene (phloroglucinol) on treatment with cerium(IV)ammonium nitrate produces 13-acetoxy-1,3,9,11-tetrahydroxy-2,10-dinitrobenzobisbenzodioxin (I) along with 1,3-dihydroxy-5-methoxy-2-nitrobenzene, 1,3,5-trihydroxy-2-nitrobenzene and 1,5-dihydroxy-3-methoxy-2-nitrobenzene, while other isomers undergo very rapid reaction with the formation of polymers which are difficult to separate.