5090-29-9

Basic information

• Product Name: 3,4-dihydroxy-α-aminoacetophenone hydrochloride
• Synonyms: 3,4-dihydroxy-α-aminoacetophenone hydrochloride;2-amino-1-(3,4-dihydroxyphenyl)ethanone,hydrochloride;Norepinephrine Impurity 1;2-AMINO-1-(3,4-DIHYDROXYPHENYL)ETHANONE,HCL
• CAS NO: 5090-29-9
• Molecular Formula: C₈H₉NO₃*ClH
• Molecular Weight: 203.6229
• Mol File: 5090-29-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 255 °C
• Boiling Point: 435.1°Cat760mmHg
• Flash Point: 217°C
• Appearance: /
• Density: 1.375g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly, Heated), Water (Very Slightly, Heated)
• CAS DataBase Reference: 3,4-dihydroxy-α-aminoacetophenone hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dihydroxy-α-aminoacetophenone hydrochloride(5090-29-9)
• EPA Substance Registry System: 3,4-dihydroxy-α-aminoacetophenone hydrochloride(5090-29-9)

Safety Data

• Hazardous Substances Data: 5090-29-9(Hazardous Substances Data)

Usage

Uses

Noradrenalone Hydrochloride is an intermediate of Norepinephrine (N674500), an antagonist of dibutyryl cyclic AMP in the regulation of narcosis. Norepinephrine modulates human dendritic cell activation by altering cytokine release.

Preparation

Preparation by demethylation of a-amino-3,4-dimethoxy-acetophenone on heating with 37% hydrochloric acid for 2.5 h at 160–165° under carbon dioxide (85%).

Synthetic route

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → norepinephrine hydrochloride (55-27-6)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 45℃; under 0.30003 - 0.375038 Torr; for 5h; Temperature; Pressure; Time;	96.7%

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) + S-(-)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeuredichlorid → S-(-)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-oxo-2-amido-ethan (104819-55-8, 104873-27-0, 104873-28-1)

Conditions	Yield
With sodium hydrogencarbonate In water; benzene for 30h;	64.3%

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) + R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeuredichlorid → R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-oxo-2-amido-ethan (104819-55-8, 104873-27-0, 104873-28-1)

Conditions	Yield
With sodium hydrogencarbonate In water; benzene for 30h;	61.4%

R,S-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeuredichlorid (941301-17-3, 941301-22-0, 104819-54-7, 104873-26-9, 104873-34-9) + 1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → R,S-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-oxo-2-amido-ethan (104819-55-8, 104873-27-0, 104873-28-1)

Conditions	Yield
With sodium hydrogencarbonate In water; benzene for 30h;	58.5%

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → noradrenalone-3-O-sulfate (80098-03-9) + noradrenalone-4-O-sulfate (80098-04-0)

Conditions	Yield
With chlorosulfonic acid at -45 - -2℃; for 1h; Yield given;

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → dl-norepinephrine-3-O-sulfate (112346-92-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 1 h / -45 - -2 °C 2: NaBH4 / methanol; propan-2-ol / 7 h View Scheme

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → dl-norepinephrine-4-O-sulfate (35538-87-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 1 h / -45 - -2 °C 2: NaBH4 / methanol; propan-2-ol / 7 h View Scheme

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → Norepinephrine (138-65-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 58.5 percent / NaHCO3 / benzene; H2O / 30 h 2: 74 percent / NaBH4 / methanol / 24 h 3: 51.4 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature View Scheme

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → norepinephrine (51-41-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 61.4 percent / NaHCO3 / benzene; H2O / 30 h 2: NaBH4 / methanol / 24 h 3: 51.4 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature View Scheme

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → D-noradrenaline (149-95-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 64.3 percent / NaHCO3 / benzene; H2O / 30 h 2: NaBH4 / methanol / 24 h 3: 54.2 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature View Scheme

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → R,S-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan (104819-57-0, 104873-30-5, 104873-31-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 58.5 percent / NaHCO3 / benzene; H2O / 30 h 2: 74 percent / NaBH4 / methanol / 24 h View Scheme

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan (104819-57-0, 104873-30-5, 104873-31-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 61.4 percent / NaHCO3 / benzene; H2O / 30 h 2: NaBH4 / methanol / 24 h View Scheme

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → S-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan (104819-57-0, 104873-30-5, 104873-31-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64.3 percent / NaHCO3 / benzene; H2O / 30 h 2: NaBH4 / methanol / 24 h View Scheme

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan (104819-57-0, 104873-30-5, 104873-31-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 61.4 percent / NaHCO3 / benzene; H2O / 30 h 2: NaBH4 / methanol / 24 h View Scheme

1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid (5090-29-9) → S-(-)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan (104819-57-0, 104873-30-5, 104873-31-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64.3 percent / NaHCO3 / benzene; H2O / 30 h 2: NaBH4 / methanol / 24 h View Scheme

Downstream Products

• 138-65-8 Norepinephrine 
• 51-41-2 norepinephrine 
• 149-95-1 D-noradrenaline 
• 104819-57-0 R,S-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan 
• 104819-57-0 R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan 
• 104819-57-0 S-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan 
• 104819-57-0 R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan 
• 104819-57-0 S-(-)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan 
• 55-27-6 norepinephrine hydrochloride 
• 35538-87-5 dl-norepinephrine-4-O-sulfate 
• 112346-92-6 dl-norepinephrine-3-O-sulfate 
• 80098-03-9 noradrenalone-3-O-sulfate 
• 80098-04-0 noradrenalone-4-O-sulfate 
• 104819-55-8 S-(-)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-oxo-2-amido-ethan