Product Name

  • Name

    N-Hydroxy-2-aminofluorene

  • EINECS
  • CAS No. 53-94-1
  • Article Data8
  • CAS DataBase
  • Density 1.325g/cm3
  • Solubility
  • 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
  • Appearance
  • Safety Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
  • Risk Codes
  • Molecular Structure Molecular Structure of 53-94-1 (N-Hydroxy-2-aminofluorene)
  • Hazard Symbols
  • Synonyms Hydroxylamine,N-fluoren-2-yl- (7CI,8CI); 2-(Hydroxyamino)fluorene;N-2-Fluorenylhydroxylamine; N-Hydroxy-2-aminofluorene; N-Hydroxy-2-fluorenamine
  • PSA 32.26000
  • LogP 3.13190

Synthetic route

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

2-nitro-9H-fluorene

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

N-(9H-fluoren-2-yl)hydroxylamine

Conditions
ConditionsYield
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;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

benzaldehyde
100-52-7

benzaldehyde

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

α-phenyl-N-(2-aminofluorenyl)nitrone

Conditions
ConditionsYield
In ethanol at 0 - 15℃;95%
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

acetyl chloride
75-36-5

acetyl chloride

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

N-Hydroxy-2-acetylaminofluoren

Conditions
ConditionsYield
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℃;
Acetyl cyanide
631-57-2

Acetyl cyanide

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

N-(9H-fluoren-2-yl)hydroxylamine

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

O-Acetyl-N-(2-fluorenyl)hydroxylamin

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at -40℃; for 2h; all steps at -40 deg C (at least);60%
N-(9H-fluoren-2-yl)hydroxylamine
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

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

Conditions
ConditionsYield
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%
n-Butyl nitrite
544-16-1

n-Butyl nitrite

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

N-(9H-fluoren-2-yl)hydroxylamine

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

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

Methoxyacetyl chloride
38870-89-2

Methoxyacetyl chloride

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

N-(9H-fluoren-2-yl)hydroxylamine

N-(2-fluorenyl)methoxyacetohydroxamic acid

N-(2-fluorenyl)methoxyacetohydroxamic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether Ambient temperature; Yield given;
nitrourea
556-89-8

nitrourea

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

N-(9H-fluoren-2-yl)hydroxylamine

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

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

Conditions
ConditionsYield
In water for 3h; Heating; Yield given;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

2,2'-azoxyfluorene

2,2'-azoxyfluorene

Conditions
ConditionsYield
With 4-nitrophenol acetate In ethanol-d6 at 22℃; for 48h;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

propionyl chloride
79-03-8

propionyl chloride

N-hydroxy-N-propionyl-2-aminofluorene

N-hydroxy-N-propionyl-2-aminofluorene

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether Ambient temperature; Yield given;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

acetic anhydride
108-24-7

acetic anhydride

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

N-Hydroxy-2-acetylaminofluoren

Conditions
ConditionsYield
In chloroform-d1 at 22℃;
With triethylamine In ethyl acetate at 20℃; for 0.5h;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

benzoyl chloride
98-88-4

benzoyl chloride

N-hydroxy-N-2-fluorenylbenzamide
3671-71-4

N-hydroxy-N-2-fluorenylbenzamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether Ambient temperature; Yield given;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

n-valeryl chloride
638-29-9

n-valeryl chloride

Pentanoic acid (9H-fluoren-2-yl)-hydroxy-amide

Pentanoic acid (9H-fluoren-2-yl)-hydroxy-amide

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether Ambient temperature; Yield given;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

methyl isocyanate
624-83-9

methyl isocyanate

N-hydroxy-N-(2-fluorenyl)-N'-methylurea

N-hydroxy-N-(2-fluorenyl)-N'-methylurea

Conditions
ConditionsYield
In benzene Ambient temperature; Yield given;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

butyryl chloride
141-75-3

butyryl chloride

N-(9H-Fluoren-2-yl)-N-hydroxy-butyramide

N-(9H-Fluoren-2-yl)-N-hydroxy-butyramide

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether Ambient temperature; Yield given;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

methyl chloroformate
79-22-1

methyl chloroformate

methyl N-hydroxy-N-(2-fluorenyl)carbamate

methyl N-hydroxy-N-(2-fluorenyl)carbamate

Conditions
ConditionsYield
In diethyl ether Ambient temperature; Yield given;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

phenyl chloroformate
1885-14-9

phenyl chloroformate

phenyl N-hydroxy-N-(2-fluorenyl)carbamate

phenyl N-hydroxy-N-(2-fluorenyl)carbamate

Conditions
ConditionsYield
In diethyl ether Yield given;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

phenylacetyl chloride
103-80-0

phenylacetyl chloride

N-(9H-Fluoren-2-yl)-N-hydroxy-2-phenyl-acetamide

N-(9H-Fluoren-2-yl)-N-hydroxy-2-phenyl-acetamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether Ambient temperature; Yield given;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

Cyclobutanecarbonyl chloride
5006-22-4

Cyclobutanecarbonyl chloride

Cyclobutanecarboxylic acid (9H-fluoren-2-yl)-hydroxy-amide

Cyclobutanecarboxylic acid (9H-fluoren-2-yl)-hydroxy-amide

Conditions
ConditionsYield
With sodium hydrogencarbonate In diethyl ether Ambient temperature; Yield given;
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

[8-13C]Guo
247226-75-1

[8-13C]Guo

A

C8-(2-aminofluorenyl)Guo

C8-(2-aminofluorenyl)Guo

B

N7-(2-aminofluorenyl)Guo

N7-(2-aminofluorenyl)Guo

Conditions
ConditionsYield
With ethylene diamine tetraacetic acid tetrasodium salt; aspirin In phosphate buffer at 23℃; for 0.283333h; pH=7.0; Product distribution; Further Variations:; Reaction partners; reaction time;
...Expand
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

2-fluoren
73051-69-1

2-fluoren

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / ethanol / 0 - 15 °C
2: 87 percent / benzene / 0.17 h / 0 °C
3: 22 percent / ethanol; various solvent(s) / 12 h / 60 °C / pH 7.0
4: 96 percent / Na2CO3; MeOH / 8 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 60 percent / Et3N / tetrahydrofuran / 2 h / -40 °C / all steps at -40 deg C (at least)
2: 14 percent / tetrahydrofuran; H2O / 1. -40 deg C 2. room temperature
View Scheme
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

N-acetoxy-N-benzoyl-2-fluorenylamine
29968-75-0

N-acetoxy-N-benzoyl-2-fluorenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / ethanol / 0 - 15 °C
2: 87 percent / benzene / 0.17 h / 0 °C
View Scheme
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

N-(benzoyl)-N-(deoxyguanosin-8-yl)-2-aminofluorene
411240-49-8

N-(benzoyl)-N-(deoxyguanosin-8-yl)-2-aminofluorene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / ethanol / 0 - 15 °C
2: 87 percent / benzene / 0.17 h / 0 °C
3: 22 percent / ethanol; various solvent(s) / 12 h / 60 °C / pH 7.0
View Scheme
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

>-2-aminofluorene
137390-96-6

>-2-aminofluorene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) NEt3, 2) aq. NaHCO3 / 1) THF, rt, 30 min, 2) 30 min, rt
2: 1) N-methylmorpholine, ClCOOiBu / 1) DMF, 15 min, -20 deg C, 2) -20 deg C, 5 min, then rt, 15 min
View Scheme
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

8-[acetyl(9H-fluoren-2-yl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine
1009639-13-7

8-[acetyl(9H-fluoren-2-yl)amino]-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / diethyl ether / 0 °C
2: caesium carbonate / 1,2-dimethoxyethane / 20 °C / Inert atmosphere
View Scheme
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

fluorene
37819-60-6

fluorene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / diethyl ether / 0 °C
2: caesium carbonate / 1,2-dimethoxyethane / 20 °C / Inert atmosphere
3: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran
View Scheme
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

8-[acetyl(2-fluorenyl)amino]-N2-[(dimethylamino)methylene]-2'-deoxyguanosine

8-[acetyl(2-fluorenyl)amino]-N2-[(dimethylamino)methylene]-2'-deoxyguanosine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydrogencarbonate / diethyl ether / 0 °C
2: caesium carbonate / 1,2-dimethoxyethane / 20 °C / Inert atmosphere
3: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran
4: pyridine / 20 °C / Inert atmosphere
View Scheme
N-(9H-fluoren-2-yl)hydroxylamine
53-94-1

N-(9H-fluoren-2-yl)hydroxylamine

8-[acetyl(2-fluorenyl)amino]-5'-O-dimethoxytrityl-N2-[(dimethylamino)methylene]-2'-deoxyguanosine

8-[acetyl(2-fluorenyl)amino]-5'-O-dimethoxytrityl-N2-[(dimethylamino)methylene]-2'-deoxyguanosine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydrogencarbonate / diethyl ether / 0 °C
2: caesium carbonate / 1,2-dimethoxyethane / 20 °C / Inert atmosphere
3: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran
4: pyridine / 20 °C / Inert atmosphere
5: pyridine / 20 °C / Inert atmosphere
View Scheme

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 NOx.

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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