53-94-1

Basic information

• Product Name: N-Hydroxy-2-aminofluorene
• Synonyms: N-Hydroxy-2-aminofluorene;2-HYDROXYLAMINOFLUORENE;9H-Fluorene-2-ylhydroxyamine;N-Hydroxy-9H-fluoren-2-amine
• CAS NO: 53-94-1
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 197.23254
• Mol File: 53-94-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 180°C (rough estimate)
• Boiling Point: 334.34°C (rough estimate)
• Flash Point: 185.8°C
• Appearance: /
• Density: 1.0957 (rough estimate)
• Vapor Pressure: 5.07E-07mmHg at 25°C
• Refractive Index: 1.6050 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 8.82±0.20(Predicted)
• Stability: Unstable in Solution
• CAS DataBase Reference: N-Hydroxy-2-aminofluorene(CAS DataBase Reference)
• NIST Chemistry Reference: N-Hydroxy-2-aminofluorene(53-94-1)
• EPA Substance Registry System: N-Hydroxy-2-aminofluorene(53-94-1)

Safety Data

• Hazardous Substances Data: 53-94-1(Hazardous Substances Data)

Usage

Uses

N-Hydroxy-2-aminofluorene is known to inactivate N-?Acetyltransferase 1 (NAT-1) whose action results in the formation of reactive, electrophilic N-?acetoxyarylamines which are considered to be the ultimate carcinogenic metabolite of certain arylamines.

InChI:InChI=1/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

Synthetic route

2-nitro-9H-fluorene (607-57-8) → N-(9H-fluoren-2-yl)hydroxylamine (53-94-1)

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;

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + benzaldehyde (100-52-7) → α-phenyl-N-(2-aminofluorenyl)nitrone (411240-48-7)

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

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + acetyl chloride (75-36-5) → N-Hydroxy-2-acetylaminofluoren (53-95-2)

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℃;

Acetyl cyanide (631-57-2) + N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) → O-Acetyl-N-(2-fluorenyl)hydroxylamin (64253-17-4)

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

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%

n-Butyl nitrite (544-16-1) + N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) → N-fluoren-2-yl-N-nitroso-hydroxylamine

Methoxyacetyl chloride (38870-89-2) + N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) → N-(2-fluorenyl)methoxyacetohydroxamic acid

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

nitrourea (556-89-8) + N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) → N-hydroxy-N-(2-fluorenyl)urea

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

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) → 2,2'-azoxyfluorene

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

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + propionyl chloride (79-03-8) → N-hydroxy-N-propionyl-2-aminofluorene

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

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + acetic anhydride (108-24-7) → N-Hydroxy-2-acetylaminofluoren (53-95-2)

Conditions	Yield
In chloroform-d1 at 22℃;
With triethylamine In ethyl acetate at 20℃; for 0.5h;

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + benzoyl chloride (98-88-4) → N-hydroxy-N-2-fluorenylbenzamide (3671-71-4)

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

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + n-valeryl chloride (638-29-9) → Pentanoic acid (9H-fluoren-2-yl)-hydroxy-amide

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

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + methyl isocyanate (624-83-9) → N-hydroxy-N-(2-fluorenyl)-N'-methylurea

Conditions	Yield
In benzene Ambient temperature; Yield given;

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + butyryl chloride (141-75-3) → N-(9H-Fluoren-2-yl)-N-hydroxy-butyramide

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

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + methyl chloroformate (79-22-1) → methyl N-hydroxy-N-(2-fluorenyl)carbamate

Conditions	Yield
In diethyl ether Ambient temperature; Yield given;

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + phenyl chloroformate (1885-14-9) → phenyl N-hydroxy-N-(2-fluorenyl)carbamate

Conditions	Yield
In diethyl ether Yield given;

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + phenylacetyl chloride (103-80-0) → N-(9H-Fluoren-2-yl)-N-hydroxy-2-phenyl-acetamide

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

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + Cyclobutanecarbonyl chloride (5006-22-4) → Cyclobutanecarboxylic acid (9H-fluoren-2-yl)-hydroxy-amide

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

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) + [8-13C]Guo (247226-75-1) → C8-(2-aminofluorenyl)Guo + N7-(2-aminofluorenyl)Guo

Conditions	Yield
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;

N-(9H-fluoren-2-yl)hydroxylamine (53-94-1) → 2-fluoren (73051-69-1)

Conditions	Yield
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-acetoxy-N-benzoyl-2-fluorenylamine (29968-75-0)

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

Conditions	Yield
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) → >-2-aminofluorene (137390-96-6)

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

Conditions	Yield
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) → fluorene (37819-60-6)

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

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

Conditions	Yield
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

Upstream product

• 53940-98-0 1,2-Methanodicyclopropa[cd,gh]pentalene-2c(1H)-methanol,hexahydro-,acetate(9CI) 
• 5394-09-2 3-cyclohexyl-4-hydroxybenzenesulfonic acid 
• 53940-90-2 (R)-2-(tert-butoxycarbonylamino)-2,3-dimethylbutanoic acid 
• 53940-88-8 BOC-ALPHA-METHYL-D-PHE 
• 53940-83-3 ALPHA-METHYL-L-VALINE HYDROCHLORIDE 
• 53940-82-2 H-ALPHA-ME-D-VAL-OH 
• 5394-08-1 2-chloroprop-2-en-1-yl 2-hydroxypropanoate 
• 53940-77-5 Cyclopentaneethanol, 2-hydroxy-1-methyl-5-(1,2,3,4-tetrahydro-6-methox y-2-naphthalenyl)-, (1S-(1-alpha,2-beta,5-beta(S*)))- 
• 53940-63-9 2-methyl-3-(pyrrolidin-1-yl)cyclohex-2-en-1-one 
• 53940-49-1 2-methoxy-4-(oxiranylmethyl)phenol 
• 5394-02-5 ethyl 2-propylidenehydrazinecarboxylate 
• 53940-11-7 METHYL 3-CYANOPYRIDINE-2-CARBOXYLATE 
• 53940-10-6 3-CYANOPYRIDINE-2-CARBOXYLIC ACID 
• 5394-00-3 1-[(1Z)-N-hydroxy-2-oxo-2-phenylethanimidoyl]pyridinium 

Downstream Products

• 5394-11-6 2-hydroxy-5-nitrobenzyl thiocyanate 
• 53941-19-8 3,4,4-Trimethyl-2-hexene 
• 53941-20-1 3-Ethyl-3-methoxy-1-pentyne 
• 5394-12-7 S-cyclohexyl phenylcarbamothioate 
• 53941-27-8 2-ISOCYANO-(INDOL-3-YL)-ACETIC ACID METHYL ESTER 
• 5394-13-8 2-BROMOBENZO[B]THIOPHENE 
• 53941-38-1 3-HYDROXYDODECANOIC ACID 
• 53941-45-0 2-PHENYLGLYCINONITRILE HYDROCHLORIDE 
• 5394-16-1 (2E)-N-phenyl-2-[(E)-phenyldiazenyl]-2-(phenylhydrazono)ethanamide 
• 5394-18-3 N-(4-Bromobutyl)phthalimide 
• 53941-83-6 benzyl (2,3-dimethyl-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl)carbamate 
• 53941-92-7 N-methylpiperidine-2-carboxamide 
• 53941-96-1 Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-2-methyl-3-methylene-, (8aS)- (9CI) 
• 5394-22-9 S-3,6-bis(2-chloroethyl)piperazine-2,5-dione 

Recommend Products

• 1137726-82-9  C₅₈H₆₄N₉O₈P 
• 37819-60-6  fluorene 
• 411240-49-8  N-(benzoyl)-N-(deoxyguanosin-8-yl)-2-aminofluorene 
• 29968-75-0  N-acetoxy-N-benzoyl-2-fluorenylamine 
• 73051-69-1  2-fluoren 
• 411240-48-7  α-phenyl-N-(2-aminofluorenyl)nitrone 
• 100-52-7  benzaldehyde 
• 103-80-0  phenylacetyl chloride 
• 53-95-2  N-Hydroxy-2-acetylaminofluoren 
• 75-36-5  acetyl chloride 
• 3671-71-4  N-hydroxy-N-2-fluorenylbenzamide 
• 98-88-4  benzoyl chloride 
• 108-24-7  acetic anhydride 
• 52663-84-0  N-hydroxy-N-propionyl-2-aminofluorene