2 - fluoro -4-- nitroaniline - CAS 369-35-7

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Category
Main Product
Product Name
2 - fluoro -4-- nitroaniline
Catalog Number
369-35-7
Synonyms
2-FLUORO-4-NITRO-PHENYLAMINE; 2-FLUORO-4-NITROANILINE; 2-Fluoro-4-niroaniline; 2-FLUORO-4-NITROANILNE; 2-Fluoro-4-nitrobenzenamine
CAS Number
369-35-7
Molecular Weight
156.11
Molecular Formula
C6H5N2O2F
Quantity
Data not available, please inquire.
COA
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MSDS
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Canonical SMILES
C1=CC(=C(C=C1[N+](=O)[O-])F)N
InChI
InChI=1S/C6H5FN2O2/c7-5-3-4(9(10)11)1-2-6(5)8/h1-3H,8H2
InChIKey
LETNCFZQCNCACQ-UHFFFAOYSA-N
Structure
CAS 369-35-7 2 - fluoro -4-- nitroaniline
Specification
Purity
N/A
Boiling Point
317.2ºC at 760 mmHg
Melting Point
126-130ºC
Density
1.448 g/cm3
Appearance
White to tan powder, crystals, crystalline powder and/or chunks
Reference Reading
1.New PET imaging agent for the serotonin transporter: [(18)F]ACF (2-[(2-amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine).
Oya S1, Choi SR, Coenen H, Kung HF. J Med Chem. 2002 Oct 10;45(21):4716-23.
A new F-18-labeled phenylthiophenyl derivative specific for imaging of serotonin transporters (SERT) in the brain by positron emission tomography (PET) is described. Fluorinated phenylthiophenyl derivative, ACF, 2-[(2-amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine, was prepared by first coupling 2,5-dichloro-4-nitroaniline with 2-mercapto-N,N-dimethylbenzamide. The amino group of the coupled adduct was converted to a fluoro group through a Schiemann reaction. Subsequently, a one pot reduction of both nitro and amide groups by BH(3)-tetrahydrofuran yielded the nonradioactive ACF (yield 25%). In vitro binding assays using cell membrane homogenates of LLC cells expressing SERT, dopamine transporters (DAT), or norepinephrine transporters (NET) showed excellent binding affinity and selectivity for SERT (K(i) = 0.05, 3020, and 650 nM for SERT, DAT, and NET, respectively). For preparation of the [(18)F]ACF, the NH(2) group of the initially coupled adduct was converted to the trimethylammonium salt, which was replaced by [(18)F]fluoride in the presence of Kryptofix 222 and potassium carbonate.
2.2,6-diarylaminotetrahydropyrans from reactions of glutaraldehyde with anilines: models for biomolecule cross-linking.
Henderson AP1, Bleasdale C, Clegg W, Golding BT. Chem Res Toxicol. 2004 Mar;17(3):378-82.
Glutaraldehyde reacts with weakly nucleophilic anilines, e.g., 3-fluoro-4-nitroaniline, which are models for amino groups in DNA, to give meso-2,6-disubstituted tetrahydropyrans, e.g., meso-2,6-di-(3-fluoro-4-nitroanilino)tetrahydropyran, that were characterized spectroscopically and by X-ray crystal structure analysis. This contrasts with the outcome of reactions with more strongly nucleophilic amines, which give rise to N-substituted 1,4-dihydropyridines. The mechanism of formation of the tetrahydropyrans is proposed to involve initial attack of the amine on one of the aldehyde groups of glutaraldehyde to give a carbinolamine intermediate. The ensuing cyclization to a tetrahydropyran, rather than dehydration to an imine leading to a dihydropyridine, is explained as a result of a competition between the lone pair of the amino function of the carbinolamine and the two lone pairs of the hydroxyl group. The formation of the tetrahydropyran is more likely with an amino function of low nucleophilicity, whereas dehydration to an imine leading to a dihydropyridine is favored with an amino function of higher nucleophilicity.
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