28149-15-7

Usage

Uses

Used in Pharmaceutical Industry:
2-nitro-9H-fluoren-9-ol is used as a chemical intermediate for the production of pharmaceuticals. It plays a crucial role in the synthesis of various medicinal compounds, contributing to the development of new drugs and therapies.
Used in Dye Industry:
2-nitro-9H-fluoren-9-ol is used as a chemical intermediate in the production of dyes. Its unique chemical structure allows for the creation of a wide range of colors, making it valuable in various applications such as textiles, plastics, and printing inks.
Used in Organic Synthesis:
2-nitro-9H-fluoren-9-ol is used as a chemical intermediate in organic synthesis. Its versatile structure enables the synthesis of various organic compounds, which can be utilized in different industries, including pharmaceuticals, materials science, and specialty chemicals.
Safety Precautions:
2-nitro-9H-fluoren-9-ol is considered to be harmful if swallowed, inhaled, or if it comes into contact with the skin. Therefore, proper safety precautions should be taken when handling this chemical compound, including the use of personal protective equipment and following established safety guidelines.

Upstream product

• 3096-52-4 2-nitro-9H-fluoren-9-one 
• 98-80-6 phenylboronic acid 
• 84459-32-5 2-bromo-5-nitrobenzaldehyde 
• 124391-53-3 2-(bromomethyl)-4-nitrobiphenyl 
• 124391-57-7 4-nitrobiphenyl-2-carbaldehyde 
• 62199-60-4 4-Nitro-2-biphenylcarboxylic acid 
• 91718-52-4 2-methyl-4-nitrobiphenyl 
• 7149-70-4 2-bromo-5-nitrotoluene 

Downstream Products

• 3096-52-4 2-nitro-9H-fluoren-9-one 
• 70-55-3 toluene-4-sulfonamide 
• 33417-27-5 2-amino-9-hydroxyfluorene 
• 78255-99-9 8-nitro-phenanthridin-6-ol 

Relevant academic research and scientific papers

Reductions of nitro and 9-oxo groups of environmental nitrofluorenes by the rat mammary gland in vitro

Nitrofluorenes and C-9-oxidized nitrofluorenes are widespread environmental genotoxins which may be relevant for breast cancer on the basis of their carcinogenicities, particularly of 2,7-dinitrofluorene (2,7-diNF), for the rat mammary gland. Since their metabolism to active carcinogens may involve nitroreduction, this study examined the reduction of 2-nitrofluorene (2-NF) and 2,7-diNF and their 9-oxo- and 9-hydroxy (OH) derivatives by the rat mammary gland. Cytosolic fractions catalyze NADH- and NADPH-dependent reductions of the 2-nitro and 9-oxo to the respective 2-amino and 9-OH compounds at rates 4- and ≥10-fold greater than those with microsomes. Rates of amine formation catalyzed by cytosol from 2,7-diNF are greater than the rate from 2-NF and increase for C-9-oxidized derivatives: 9-oxo-2-NF >> 9-OH-2-NF > 2-NF and 9-OH-2,7-diNF 9-oxo-2,7-diNF >> 2,7-diNF. Nitroreduction is inhibited by O2 or allopurinol (20 μM), dicoumarol (100 μM), and rutin (50 μM). 9-Oxoreduction is inhibited by rutin, dicoumarol, and indomethacin (100 μM), but not by O2 or allopurinol. Pyrazole or menadione does not inhibit nitro or 9-oxoreduction. Xanthine, hypoxanthine, 2-hydroxypyrimidine, and N'-methylnicotinamide support cytosol-catalyzed nitro, but not 9-oxo, reduction. The data suggest that the nitroreduction is catalyzed largely by a xanthine oxidase and partially by a diaphorase and 9-oxoreduction by a carbonyl reductase. The extents of the nitro and carbonyl reductions of the nitrofluorenes may determine their reactivities with DNA, and thus genotoxicities for the mammary gland.

Preneoplastic lesions, DNA adduct formation and mutagenicity of 5-, 7- and 9 -hydroxy-2-nitrofluorene, metabolites of the air pollutant 2-nitrofluorene

The metabolites of 2-nitrofluorene (NF), 5-, 7- and 9-OH-2-nitrofluorene (OH-NF) were compared for their genotoxicity. Seventy-two hours after intraperitoneal administration of these substances individually to rats (100 mg/kg body wt.), DNA adducts in liver tissue were analyzed with 32P-TLC and 32P-HPLC. An in vivo liver model was used to test the initiating capacity of the said substances for the formation of preneoplastic lesions. 5-OH-NF showed low capacity to induce DNA adduct formation and low potential as initiator to induce preneoplastic lesions-foci/nodules in the liver of rats. Both 7- and 9-OH-NF induced DNA adducts and preneoplastic liver lesions but with smaller quantities compared to NF. It seems that 7- and 9-OH-NF can not be considered as detoxification products of NF. In general, the initiating capacity of these substances for the formation of preneoplastic lesions has a good correlation with their potency to form DNA adducts.

Regiospecific Syntheses of All Isomeric Nitrofluorenones and Nitrofluorenes by Transition Metal Catalyzed Cross-Coupling Reactions

Regiospecific efficient syntheses of 1-, 2-, 3-, and 4-nitrofluorenones 8 and the corresponding nitrofluorenes 10 by palladium(0)-catalyzed cross-coupling reactions of aryl boronic acids 1 with bromonitrotoluenes 2 and bromonitrobenzene 3 are described.