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Name	N-Hydroxy-2-aminofluorene	EINECS	N/A
CAS No.	53-94-1	Density	1.325g/cm³
PSA	32.26000	LogP	3.13190
Solubility	N/A	Melting Point	180°C (rough estimate)
Formula	C13H11 N O	Boiling Point	397.2°Cat760mmHg
Molecular Weight	197.236	Flash Point	185.8°C
Transport Information	N/A	Appearance	N/A
Safety	Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	Hydroxylamine,N-fluoren-2-yl- (7CI,8CI); 2-(Hydroxyamino)fluorene;N-2-Fluorenylhydroxylamine; N-Hydroxy-2-aminofluorene; N-Hydroxy-2-fluorenamine	Article Data	8

N-Hydroxy-2-aminofluorene Synthetic route

: 607-57-8
2-nitro-9H-fluorene

: 53-94-1
N-(9H-fluoren-2-yl)hydroxylamine

Conditions

Conditions	Yield
With ammonium chloride; D,L-histidine; zinc at 20 - 30℃; for 0.75h; pH=7.4 - 7.5;	91%
With hydrazine hydrate In ethanol; 1,2-dichloro-ethane for 1h;	66%
With hydrazine hydrate; palladium on activated charcoal In tetrahydrofuran at 0℃; for 1h;

: 53-94-1
N-(9H-fluoren-2-yl)hydroxylamine

: 100-52-7
benzaldehyde

: 411240-48-7
α-phenyl-N-(2-aminofluorenyl)nitrone

Conditions

Conditions	Yield
In ethanol at 0 - 15℃;	95%

: 53-94-1
N-(9H-fluoren-2-yl)hydroxylamine

: 75-36-5
acetyl chloride

: 53-95-2
N-Hydroxy-2-acetylaminofluoren

Conditions

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether at 20℃; for 1h;	78%
With sodium hydrogencarbonate; triethylamine 1) THF, rt, 30 min, 2) 30 min, rt; Yield given. Multistep reaction;
With sodium hydrogencarbonate In diethyl ether at 0℃;

: 631-57-2
Acetyl cyanide

: 53-94-1
N-(9H-fluoren-2-yl)hydroxylamine

: 64253-17-4
O-Acetyl-N-(2-fluorenyl)hydroxylamin

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at -40℃; for 2h; all steps at -40 deg C (at least);	60%

: 53-94-1
N-(9H-fluoren-2-yl)hydroxylamine

: benzyl N-[(3S,6S)-2-(9H-fluoren-2-yl)-6-methyl-3,6-dihydro-2H-1,2-oxazin-3-yl]carbamate

Conditions

Conditions	Yield
Stage #1: N-(9H-fluoren-2-yl)hydroxylamine With 3-chloro-benzenecarboperoxoic acid In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at -65℃; for 0.0833333h; Inert atmosphere; Stage #3: With benzyl ((1E,3E)-penta-1,3-dien-1-yl)carbamate In toluene at -65℃; for 72h; Diels-Alder Cycloaddition; Inert atmosphere; stereoselective reaction;	59%

Yield

Stage #1: N-(9H-fluoren-2-yl)hydroxylamine With 3-chloro-benzenecarboperoxoic acid In toluene at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at -65℃; for 0.0833333h; Inert atmosphere;
Stage #3: With benzyl ((1E,3E)-penta-1,3-dien-1-yl)carbamate In toluene at -65℃; for 72h; Diels-Alder Cycloaddition; Inert atmosphere; stereoselective reaction;

59%

: 544-16-1
n-Butyl nitrite

: 53-94-1
N-(9H-fluoren-2-yl)hydroxylamine

: N-fluoren-2-yl-N-nitroso-hydroxylamine

: 38870-89-2
Methoxyacetyl chloride

: 53-94-1
N-(9H-fluoren-2-yl)hydroxylamine

: N-(2-fluorenyl)methoxyacetohydroxamic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether Ambient temperature; Yield given;

: 556-89-8
nitrourea

: 53-94-1
N-(9H-fluoren-2-yl)hydroxylamine

: N-hydroxy-N-(2-fluorenyl)urea

Conditions

Conditions	Yield
In water for 3h; Heating; Yield given;

: 53-94-1
N-(9H-fluoren-2-yl)hydroxylamine

: 2,2'-azoxyfluorene

Conditions

Conditions	Yield
With 4-nitrophenol acetate In ethanol-d6 at 22℃; for 48h;

: 53-94-1
N-(9H-fluoren-2-yl)hydroxylamine

: 79-03-8
propionyl chloride

: N-hydroxy-N-propionyl-2-aminofluorene

Conditions

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether Ambient temperature; Yield given;

N-Hydroxy-2-aminofluorene Chemical Properties

Empirical Formula of N-Hydroxy-2-aminofluorene (CAS NO.53-94-1): C₁₃H₁₁NO
Molecular Weight: 197.2325
Index of Refraction: 1.744
Density: 1.325 g/cm³
Flash Point: 185.8 °C
Enthalpy of Vaporization: 68.29 kJ/mol
Boiling Point: 397.2 °C at 760 mmHg
Vapour Pressure: 5.07E-07 mmHg at 25 °C
Structure of N-Hydroxy-2-aminofluorene (CAS NO.53-94-1):

IUPAC Name: N-(9H-Fluoren-2-yl)hydroxylamine
Canonical SMILES: C1C2=CC=CC=C2C3=C1C=C(C=C3)NO
InChI: InChI=1S/C13H11NO/c15-14-11-5-6-13-10(8-11)7-9-3-1-2-4-12(9)13/h1-6,8,14-15H,7H2
InChIKey: JJCLXJPUTJMRTM-UHFFFAOYSA-N

N-Hydroxy-2-aminofluorene Toxicity Data With Reference

1.	mmo-sat 50 ng/plate	CBINA8 Chemico-Biological Interactions. 54 (1985),71.
2.	dns-hmn:oth 100 nmol/L	JJIND8 JNCI, Journal of the National Cancer Institute. 72 (1984),847.
3.	dnd-mus:lvr 5 µmol/L	CRNGDP Carcinogenesis. 5 (1984),797.
4.	ipr-gpg TDLo:1600 mg/kg/17W-I:CAR	CNREA8 Cancer Research. 24 (1964),2018.

N-Hydroxy-2-aminofluorene Consensus Reports

EPA Genetic Toxicology Program.

N-Hydroxy-2-aminofluorene Safety Profile

Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Human mutation data reported. When heated to decomposition N-Hydroxy-2-aminofluorene (CAS NO.53-94-1) emits toxic fumes of NO_x.

N-Hydroxy-2-aminofluorene Specification

N-Hydroxy-2-aminofluorene , its cas register number is 53-94-1. It also can be called 9H-Fluoren-2-amine, N-hydroxy- ; N-Hydroxy-2-fluorenamine ; N-2-Fluorenylhydroxylamine ; and Hydroxylamine, N-fluoren-2-yl- .

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