344-80-9

Basic information

• Product Name: 2-Amino-2'-fluoro-5-nitrobenzophenone
• Synonyms: 2-Amino-2'-fluoro-5-Nitryl-diphenylmethanone;2-Amino-5-nitro-2'-fluorobenzophenone;2-Amino-5-nitrophenyl(2-fluorophenyl) ketone;(2-azanyl-5-nitro-phenyl)-(2-fluorophenyl)methanone;2-[(2-fluorophenyl)carbonyl]-4-nitroaniline;2-Amino-5-Nitro-2'-Fluorobenzophenone (FNAB);2-AMINO-2'-FLUORO-5-NITROBENZOPHENONE;(2-AMINO-5-NITRO-PHENYL)-(2-FLUORO-PHENYL)-METHANONE
• CAS NO: 344-80-9
• Molecular Formula: C₁₃H₉FN₂O₃
• Molecular Weight: 260.22
• EINECS: 206-454-8
• Product Categories: Aromatic Benzophenones & Derivatives (substituted);Amines;Aromatics;Intermediates
• Mol File: 344-80-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 158-160°C
• Boiling Point: 485.6 °C at 760 mmHg
• Flash Point: 247.5 °C
• Appearance: /
• Density: 1.399 g/cm³
• Storage Temp.: Refrigerator
• PKA: -3.19±0.36(Predicted)
• CAS DataBase Reference: 2-Amino-2'-fluoro-5-nitrobenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-2'-fluoro-5-nitrobenzophenone(344-80-9)
• EPA Substance Registry System: 2-Amino-2'-fluoro-5-nitrobenzophenone(344-80-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 344-80-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Intermediate in the production of Flunitrazepam metabolites.

Synthetic route

5-(2-fluorophenyl)-1,3-dihydro-7-nitro-2H-1,4-benzodiazepin-2-one (2558-30-7) → 2-amino-5-nitro-2'-fluorobenzophenone (344-80-9)

Conditions	Yield
With hydrogenchloride In ethanol Heating;

2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) + chloroacetyl chloride (79-04-9) → 2‑(2‑chloroacetamido)‑5‑nitro‑2′‑fluorobenzophenone

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h;	95%

diazoacetic acid ethyl ester (623-73-4) + 2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → C17H15FN2O5

Conditions	Yield
With 1-methylimidazolium tetrafluoroborate In neat (no solvent) at 20℃; for 2h;	90%

2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) + N-(Benzyloxycarbonyl)glycine (1138-80-3) → Benzyl{[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]methyl}-carbamate

Conditions	Yield
With thionyl chloride; sodium hydrogencarbonate In tetrahydrofuran; ethyl acetate

N-Cbz-Ala (1142-20-7) + 2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → (S)-benzyl-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]ethyl}carbamate (59937-53-0)

Conditions	Yield
With thionyl chloride; sodium hydrogencarbonate In tetrahydrofuran

chloroacetaldehyde dimethyl acetal (97-97-2) + 2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → 2-chloromethyl-4-(2-fluoro-phenyl)-6-nitro-1,2-dihydro-quinazoline 3-oxide (59468-08-5)

Conditions	Yield
With hydrogenchloride In ethanol

N-Cbz-Ala (1142-20-7) + 2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → (-)-benzyl-[1-[{2-(o-fluorobenzoyl)-4-nitrophenyl}-carbamoyl]ethyl]carbamate (74892-38-9)

Conditions	Yield
With phosphorus pentachloride In dichloromethane; toluene

2-(α-bromo-α-fluoroacetamido)-5-nitro-2'-fluorobenzophenone + bromo-fluoro-acetyl bromide (359-22-8) + 2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → 2-(α-amino-α-fluoroacetamido)-5-nitro-2'-fluorobenzophenone + 3-fluoro-5-o-fluorophenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one (60628-63-9)

Conditions	Yield
With hexamethylenetetramine In ethanol

2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → 7-amino-2-aminomethyl-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepine

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / ethanol 2: manganese dioxide / tetrahydrofuran; dichloromethane 3: acetic acid / nitromethane; dichloromethane; dimethyl sulfoxide 4: ethanol View Scheme

2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → 1,3-dihydro-5-(2-fluorophenyl)-7-nitro-2-nitromethylene-2H-1,4-benzodiazepine 4-oxide

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol 2: manganese dioxide / tetrahydrofuran; dichloromethane 3: acetic acid / nitromethane; dichloromethane; dimethyl sulfoxide View Scheme

2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → 2-chloromethyl-4-(2-fluoro-phenyl)-6-nitro-quinazoline 3-oxide (59468-09-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol 2: manganese dioxide / tetrahydrofuran; dichloromethane View Scheme

2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → 5-(2-fluorophenyl)-1,3-dihydro-7-nitro-2H-1,4-benzodiazepin-2-one (2558-30-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 12 h / 0 - 20 °C 2: hexamethylenetetramine; ammonium chloride / ethanol / 4 h / Reflux View Scheme

2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → C19H19FN3O6P

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dichloromethane / 12 h / 0 - 20 °C 2.1: hexamethylenetetramine; ammonium chloride / ethanol / 4 h / Reflux 3.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 3.2: 0.58 h / -20 - 0 °C / Inert atmosphere View Scheme

2-amino-5-nitro-2'-fluorobenzophenone (344-80-9) → 8‑nitro‑6‑(2‑fluorophenyl)‑3‑(4‑toluenesulfonyl)‑4H‑imidazo[1,5‑a][1,4]benzodiazepine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: dichloromethane / 12 h / 0 - 20 °C 2.1: hexamethylenetetramine; ammonium chloride / ethanol / 4 h / Reflux 3.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 3.2: 0.58 h / -20 - 0 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 4 h / -20 - 20 °C / Inert atmosphere View Scheme

Upstream product

• 2558-30-7 5-(2-fluorophenyl)-1,3-dihydro-7-nitro-2H-1,4-benzodiazepin-2-one 

Downstream Products

• 59468-08-5 2-chloromethyl-4-(2-fluoro-phenyl)-6-nitro-1,2-dihydro-quinazoline 3-oxide 
• 2558-30-7 5-(2-fluorophenyl)-1,3-dihydro-7-nitro-2H-1,4-benzodiazepin-2-one 
• 59468-09-6 2-chloromethyl-4-(2-fluoro-phenyl)-6-nitro-quinazoline 3-oxide 
• 60628-63-9 3-fluoro-5-o-fluorophenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one 
• 74892-38-9 (-)-benzyl-[1-[{2-(o-fluorobenzoyl)-4-nitrophenyl}-carbamoyl]ethyl]carbamate 
• 59937-53-0 (S)-benzyl-{1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]ethyl}carbamate