33417-27-5

Basic information

• Product Name: 2-AMINO-9-FLUORENOL
• Synonyms: 2-AMINO-9-HYDROXYFLUORENE;2-AMINO-9-FLUORENOL;2-amino-fluoren-9-o;2-AMINO-9-FLUOROENONE;2-Amino-9H-fluoren-9-ol
• CAS NO: 33417-27-5
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 197.23
• Product Categories: Fluorenes, Flurenones
• Mol File: 33417-27-5.mol

Chemical Properties

• Melting Point: 197-199 °C(lit.)
• Boiling Point: 444.3°Cat760mmHg
• Flash Point: 222.5°C
• Appearance: /
• Density: 1.336g/cm³
• Vapor Pressure: 1.12E-08mmHg at 25°C
• Refractive Index: 1.741
• CAS DataBase Reference: 2-AMINO-9-FLUORENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-9-FLUORENOL(33417-27-5)
• EPA Substance Registry System: 2-AMINO-9-FLUORENOL(33417-27-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RTECS: LL8410000
• Hazardous Substances Data: 33417-27-5(Hazardous Substances Data)

Usage

Main Properties

1. Chemical Formula: C13H11NO
2. Functional Groups:
Primary amine group ( -NH2 )
Hydroxyl group ( -OH )
3. Derivation: Derived from fluorene
4. Fluorescent Properties: Exhibits fluorescence
5. Applications:
Organic Chemistry Reagent: Used in the synthesis of various organic compounds
Fluorescent Probe: Utilized in biological and environmental research
Pharmaceutical and Material Development: Potential applications in pharmaceuticals and materials due to its unique structure and properties

Specific Content

1. Chemical Name: 2-Amino-9-fluorenol
2. Alternative Name: 9-Hydroxyfluorene-2-amine
3. Composition: Contains 13 carbon atoms, 11 hydrogen atoms, 1 nitrogen atom, and 1 oxygen atom
4. Functional Group Positioning: Primary amine group is located at position 2 and the hydroxyl group is located at position 9 on the fluorene ring.
5. Utility in Organic Synthesis: Facilitates the creation of diverse organic compounds through chemical reactions.
6. Fluorescence Application: Used to label biomolecules or environmental components for visualization under fluorescence microscopy.
7. Potential in Pharmaceutical Development: Being explored for its pharmacological properties and potential in drug discovery.
8. Material Science Exploration: Investigated for its suitability in designing novel materials with specific properties.

This compound, with its dual functional groups and fluorescent nature, holds promise in various fields of science, from organic chemistry to materials science and biomedical research.

InChI:InChI=1/C13H11NO/c14-8-5-6-10-9-3-1-2-4-11(9)13(15)12(10)7-8/h1-7,13,15H,14H2

Upstream product

• 63621-13-6 2-Amino-9-diazofluoren 
• 857789-09-4 2-amino-fluoren-9-one-hydrazone 
• 3096-56-8 2-bromofluoren-9-one 
• 3096-52-4 2-nitro-9H-fluoren-9-one 
• 28149-15-7 9-Hydroxy-2-nitrofluorene 
• 64-17-5 ethanol 
• 3096-57-9 2-amino-9-fluorenone 
• 555-31-7 aluminum isopropoxide 

Downstream Products

• 102023-99-4 2-benzylidenamino-fluoren-9-ol 
• 108973-47-3 2-acetamido-9H-fluoren-9-yl acetate 
• 57229-41-1 9-Hydroxy-2-acetylaminofluorene 

Relevant articles and documents

Integrin receptor inhibitors

Provided are compounds of formula (I) wherein A, Q, W, X, Y, Z, R1 to R4, m and n are as defined herein. Compounds of the invention bind to α4 integrin receptors and thereby inhibit binding of ligands for α4 int

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.

Nitroreduction of nitrated and C-9 oxidized fluorenes in vitro

Widespread environmental pollution with mutagenic and carcinogenic nitrofluorenes contributes to human health risks. Since nitroreduction leads to activation of many nitro compounds, nitroreduction of the nitrofluorene (NF) derivatives by one- and two-electron reductants was examined. Rates of nitroreduction catalyzed by xanthine oxidase (XO)/hypoxanthine and measured via stimulation of acetylated cytochrome c reduction increased with the number of nitro groups and oxidation at C-9: 9-oxo-2,4,7-triNF > 9-oxo-2,7- diNF > 2,7-diNF > 9-oxo-2-NF = 2,5-diNF > 9-hydroxy-2-NF > 2-NF. Ascorbate catalyzed one-electron reduction to nitro anion radicals which reacted with molecular O2 to yield superoxide. Rates of O2 uptake with 9-oxo-2,4,7- triNF and 9-oxo-2,7-diNF were 63 and 0.17 times those, respectively, with equivalent concentrations of nitrofurazone, a classical substrate. Superoxide formation was indicated by the ~75% regeneration of O2 upon addition of superoxide dismutase and catalase. 9-Oxo-2,4,7-triNF stimulated O2 uptake in the presence of XO/NADH with typical Michaelis-Menten kinetics with an apparent K(m) of 0.476 ± 0.054 μM versus a K(m) of 6.18 ± 0.719 μM for nitrofurazone. HPLC analyses of products from reduction catalyzed by XO or diaphorase of Clostridium with NADH showed the following trends for the rates of amine formation from 9-oxo-2,7-diNF > 2,7-diNF; 9-oxo-2-NF > 9-hydroxy-2- NF > 2-NF; 2,7-diNF > 2-NF; and 9-oxo-2,7-diNF > 9-oxo-2-NF. Little or no amine was formed in 95% O2, suggesting O2-labile intermediates. The data herein suggest that oxidation at C-9 and multiple nitro groups increase the potential for nitroreduction of the nitrofluorenes in vivo which may lead to genotoxic effects.