7644-04-4

Basic information

• Product Name: 2-Amino-4'-bromoacetophenone
• Synonyms: 2-AMINO-4'-BROMOACETOPHENONE;α-Amino-4’-bromoacetophenone;a-Amino-4-bromoacetophenone;a-Amino-4-bromoacetophenone hydrochloride;2-aMino-1-(4-broMophenyl)ethan-1-one
• CAS NO: 7644-04-4
• Molecular Formula: C₈H₈BrNO
• Molecular Weight: 214.06
• Mol File: 7644-04-4.mol

Chemical Properties

• Boiling Point: 322.8 °C at 760 mmHg
• Flash Point: 149 °C
• Appearance: /
• Density: 1.52 g/cm³
• CAS DataBase Reference: 2-Amino-4'-bromoacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4'-bromoacetophenone(7644-04-4)
• EPA Substance Registry System: 2-Amino-4'-bromoacetophenone(7644-04-4)

Safety Data

• Hazardous Substances Data: 7644-04-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Amino-4'-bromoacetophenone is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique structural features and reactivity, contributing to the development of new drugs with potential therapeutic applications.
Used in Organic Compounds Synthesis:
As a versatile building block, 2-Amino-4'-bromoacetophenone is utilized in the synthesis of a wide range of organic compounds, enhancing the diversity and complexity of chemical structures that can be achieved in organic chemistry.
Used in Dye Production:
2-Amino-4'-bromoacetophenone is used as a precursor in the production of dyes, leveraging its chemical properties to create colorants for various applications, including textiles, plastics, and printing inks.
Used in Polymer Production:
2-Amino-4'-bromoacetophenone is also employed in the synthesis of polymers, where its structural elements can influence the polymer's properties, such as color, stability, and reactivity, contributing to the development of specialty polymers for specific industrial needs.
Used in Specialty Chemicals:
2-Amino-4'-bromoacetophenone finds application in the production of specialty chemicals, where its unique combination of functional groups and substituents can be tailored to meet the requirements of niche chemical markets.
Safety Considerations:
It is crucial to handle 2-Amino-4'-bromoacetophenone with care, as it may pose health risks if ingested or inhaled and can cause skin and eye irritation upon contact. Proper safety measures, including the use of personal protective equipment and adherence to material safety data sheets, are essential when working with this compound.

Synthetic route

para-bromophenacyl bromide (99-73-0) → 4-bromophenacylamine (7644-04-4)

Conditions	Yield
With hexamethylenetetramine In toluene at 40℃; for 16h; Inert atmosphere;	92%
Stage #1: para-bromophenacyl bromide With hexamethylenetetramine In chloroform at 60℃; for 5h; Stage #2: With hydrogenchloride In ethanol; water at 85℃; for 14h;	69%
With hexamethylenetetramine; sodium iodide In ethanol; chloroform for 24h; Ambient temperature;

N-(2-(4-bromophenyl)-2-oxoethyl)picolinamide → 4-bromophenacylamine (7644-04-4)

Conditions	Yield
Stage #1: N-(2-(4-bromophenyl)-2-oxoethyl)picolinamide With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With zinc In tetrahydrofuran; water at 20℃; for 1.5h; Inert atmosphere;	30%

1-(4-bromophenyl)ethylamine (24358-62-1) → 4-bromophenacylamine (7644-04-4)

<4-bromo-phenacyl>-hexamethylenetetraminium bromide → 4-bromophenacylamine (7644-04-4)

Conditions	Yield
With hydrogenchloride

4-bromophenacylamine (7644-04-4) → 4-Bromophenylethanolamine (41147-82-4)

Conditions	Yield
With potassium hydroxide In isopropyl alcohol at 100℃; Microwave irradiation;	95%
With sodium tetrahydroborate In methanol at 0℃; for 0.5h;

2-Picolinic acid (98-98-6) + 4-bromophenacylamine (7644-04-4) → N-(2-(4-bromophenyl)-2-oxoethyl)picolinamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 16h; Inert atmosphere;	86%
Stage #1: 2-Picolinic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -15℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromophenacylamine In dichloromethane at -15 - 20℃; Inert atmosphere;

2-(3-(2,5-dimethylphenoxy)propyl)-2-methylpropionyl chloride (79791-29-0) + 4-bromophenacylamine (7644-04-4) → C23H28BrNO3

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	81%

4-bromophenacylamine (7644-04-4) + 2-isocyanatobenzonitrile (42066-86-4) → 1-[2-(4-bromo-phenyl)-2-oxo-ethyl]-3-(2-cyano-phenyl)-urea (603069-36-9)

Conditions	Yield
With triethylamine In dichloromethane for 0.666667h; Heating;	78%

4-bromophenacylamine (7644-04-4) + 4-(6,7-dimethoxy-4-quinazolinyl)-1-piperazinecarboxylic acid chloride (41647-74-9) → 4-(6,7-dimethoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid [2-(4-bromo-phenyl)-2-oxo-ethyl]-amide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	72%

4-bromophenacylamine (7644-04-4) + 3-(2,4-dioxo-3,4,7,8-tetrahydro-2H,5H-thiopyrano[4,3-d]pyrimidin-1-yl)-propionic acid (425634-93-1) → N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-3-(2,4-dioxo-3,4,7,8-tetrahydro-2H,5H-thiopyrano[4,3-d]pyrimidin-1-yl)-propionamide (425635-00-3)

Conditions	Yield
With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 18h;

4-bromophenacylamine (7644-04-4) + 3-(2,4-dioxo-3,4,5,6,7,8-hexahydro-2H-quinazolin-1-yl)-propionic acid (425634-90-8) → N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-3-(2,4-dioxo-3,4,5,6,7,8-hexahydro-2H-quinazolin-1-yl)-propionamide

Conditions	Yield
With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 18h;

4-bromophenacylamine (7644-04-4) + 3-acetyl-4-methoxy-2H-chromen-2-one (71703-23-6) → 3-acetyl-4-[2-(4-bromo-phenyl)-2-oxo-ethylamino]-chromen-2-one (535921-03-0)

Conditions	Yield
With triethylamine In methanol at 20℃; for 0.5h;

4-bromophenacylamine (7644-04-4) + 3-benzoyl-4-methoxycoumarin (535921-01-8) → 3-benzoyl-4-[2-(4-bromo-phenyl)-2-oxo-ethylamino]-chromen-2-one (535921-06-3)

Conditions	Yield
With triethylamine In methanol at 20℃; for 0.5h;

nicotinic acid (59-67-6) + 4-bromophenacylamine (7644-04-4) → N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-nicotinamide (13337-78-5)

Conditions	Yield
With diisopropyl-carbodiimide In N,N-dimethyl-formamide

pyridine-4-carboxylic acid (55-22-1) + 4-bromophenacylamine (7644-04-4) → N-(4'-bromophenacyl)isonicotinamide (151427-14-4)

Conditions	Yield
With diisopropyl-carbodiimide In N,N-dimethyl-formamide

6-methylnicotinic acid (3222-47-7) + 4-bromophenacylamine (7644-04-4) → N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-6-methyl-nicotinamide

Conditions	Yield
With diisopropyl-carbodiimide In N,N-dimethyl-formamide

Nicotinic acid N-oxide (2398-81-4) + 4-bromophenacylamine (7644-04-4) → N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-1-oxy-nicotinamide

Conditions	Yield
With diisopropyl-carbodiimide In N,N-dimethyl-formamide

6-Chloro-3-pyridinecarboxylic acid (5326-23-8) + 4-bromophenacylamine (7644-04-4) → N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-6-chloro-nicotinamide

Conditions	Yield
With diisopropyl-carbodiimide In N,N-dimethyl-formamide

2-pyridinecarboxylic acid N-oxide (824-40-8) + 4-bromophenacylamine (7644-04-4) → 1-oxy-pyridine-2-carboxylic acid [2-(4-bromo-phenyl)-2-oxo-ethyl]-amide

Conditions	Yield
With diisopropyl-carbodiimide In N,N-dimethyl-formamide

2-chloronicotinic acid (2942-59-8) + 4-bromophenacylamine (7644-04-4) → N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-2-chloro-nicotinamide

Conditions	Yield
With diisopropyl-carbodiimide In N,N-dimethyl-formamide

2-aminopyridin-3-carboxylic acid (5345-47-1) + 4-bromophenacylamine (7644-04-4) → 2-amino-N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-nicotinamide

Conditions	Yield
With diisopropyl-carbodiimide In N,N-dimethyl-formamide

Isonicotinic acid N-oxide (13602-12-5) + 4-bromophenacylamine (7644-04-4) → N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-1-oxy-isonicotinamide

Conditions	Yield
With diisopropyl-carbodiimide In N,N-dimethyl-formamide

Upstream product

• 24358-62-1 1-(4-bromophenyl)ethylamine 
• 99-73-0 para-bromophenacyl bromide 

Downstream Products

• 5467-72-1 α-amino-4-bromoacetophenone hydrochloride 
• 425635-00-3 N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-3-(2,4-dioxo-3,4,7,8-tetrahydro-2H,5H-thiopyrano[4,3-d]pyrimidin-1-yl)-propionamide 
• 13337-78-5 N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-nicotinamide 
• 151427-14-4 N-(4'-bromophenacyl)isonicotinamide 
• 20034-54-2 4-(4-bromophenyl)-2-phenyl-2H-[1,2,3]triazole 

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