28149-15-7

Basic information

• Product Name: 2-nitro-9H-fluoren-9-ol
• Synonyms: 2-Nitro-9H-fluoren-9-ol; 9H-fluoren-9-ol, 2-nitro-
• CAS NO: 28149-15-7
• Molecular Formula: C₁₃H₉NO₃
• Molecular Weight: 227.2155
• Mol File: 28149-15-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 436.5°C at 760 mmHg
• Flash Point: 190.7°C
• Density: 1.445g/cm³
• Vapor Pressure: 2.16E-08mmHg at 25°C
• Refractive Index: 1.717
• CAS DataBase Reference: 2-nitro-9H-fluoren-9-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-nitro-9H-fluoren-9-ol(28149-15-7)
• EPA Substance Registry System: 2-nitro-9H-fluoren-9-ol(28149-15-7)

Safety Data

• Hazardous Substances Data: 28149-15-7(Hazardous Substances Data)

Usage

General Description

2-nitro-9H-fluoren-9-ol, also known as 2-nitro-1,2,3,4-tetrahydro-9H-fluorene-9-ol, is a chemical compound with the molecular formula C13H11NO3. It is a nitro-derivative of fluorene, consisting of a fluorene core with a nitro group and a hydroxyl group attached at the 2 and 9 positions, respectively. 2-nitro-9H-fluoren-9-ol is mainly used in the production of pharmaceuticals, dyes, and organic synthesis. It is also used as a chemical intermediate in the manufacturing of other organic compounds. 2-nitro-9H-fluoren-9-ol is considered to be harmful if swallowed, inhaled, or if it comes into contact with the skin, and proper safety precautions should be taken when handling it.

Upstream product

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

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 articles and documents

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.

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.