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299758

Sigma-Aldrich

2-Nitro-9-fluorenone

99%

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About This Item

Empirical Formula (Hill Notation):
C13H7NO3
CAS Number:
Molecular Weight:
225.20
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

solid

mp

222-223 °C (lit.)

SMILES string

[O-][N+](=O)c1ccc2-c3ccccc3C(=O)c2c1

InChI

1S/C13H7NO3/c15-13-11-4-2-1-3-9(11)10-6-5-8(14(16)17)7-12(10)13/h1-7H

InChI key

AJEAHBZZHSLIQP-UHFFFAOYSA-N

General description

2-Nitro-9-fluorenone is a mutagenic photoproduct of u.v.a.-irradiated 2-aminofluorene. 2-Nitro-9-fluorenone was isolated from diesel-exhaust particles using a two-step fractionation scheme consisting of Sephadex LH20 chromatography and silica-gel thin-layer chromatography. Submicromolar concentrations of 2-nitro-9-fluorenone were quantitated by mercury meniscus modified silver solid amalgam electrode combined with direct current voltammetry or differential pulse voltammetry.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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G F Strniste et al.
Carcinogenesis, 7(3), 499-502 (1986-03-01)
Exposure of solutions of 2-aminofluorene (2-AF, dissolved in dimethylsulfoxide) to near ultraviolet light (u.v.a. wavelengths of 320-400 nm) results in the formation of a variety of photo-products, several of which are direct-acting mutagens in the Ames/Salmonella standard-plate assay. Previously published
S Itoh et al.
Biochemistry, 30(22), 5340-5346 (1991-06-04)
One-carbonyl quinonoid compounds, fluorenone (fluoren-9-one), anthrone, and their derivatives are introduced into spinach photosystem (PS) I reaction centers in place of the intrinsic secondary electron acceptor phylloquinone (= vitamin K1). Anthrone and 2-nitrofluorenone fully mediated the electron-transfer reaction between the
2-Nitrofluorene and related compounds: prevalence and biological effects.
B Beije et al.
Mutation research, 196(2), 177-209 (1988-09-01)
Voltammetric Determination of Genotoxic Nitro Derivatives of Fluorene and 9-Fluorenone Using a Mercury Meniscus Modified Silver Solid Amalgam Electrode.
Vyskocil V, et al.
Electroanalysis, 22(17-18), 2034-2042 (2010)
B Henkel et al.
Journal of peptide science : an official publication of the European Peptide Society, 7(3), 152-156 (2001-04-12)
This paper presents a new protecting group, the (2-nitrofluoren-9-yl)methoxycarbonyl group. Investigations on the properties of this new modification of the Fmoc-system, such as the solvent-dependent photochemical cleavage, and enhanced lability towards bases, are described, as well as UV-kinetic measurements of

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