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
• Article Data: 10

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

General Description

2-Amino-4'-bromoacetophenone is a chemical compound that is a derivative of acetophenone, containing a bromine substituent at the 4' position and an amino group at the 2 position. It is commonly used in the synthesis of various pharmaceuticals and organic compounds, due to its reactivity and versatility as a building block in organic chemistry. 2-Amino-4'-bromoacetophenone has potential applications in the production of dyes, polymers, and other specialty chemicals. It is important to handle 2-Amino-4'-bromoacetophenone with caution, as it may be harmful if ingested or inhaled and can cause irritation to skin and eyes upon contact.

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

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

Downstream Products

• 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 
• 151427-14-4 N-(4'-bromophenacyl)isonicotinamide 
• 13337-78-5 N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-nicotinamide 
• 1467061-25-1 N-(2-(4-bromophenyl)-2-hydroxyethyl)-2-chloroacetamide 
• 1368418-27-2 6-(4-bromophenyl)morpholin-3-one 

Relevant articles and documents

Design, synthesis, and cytotoxic activity of novel 2H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidine derivatives

In this study, a series of novel 2H-imidazo [1, 2-c] pyrazolo [3, 4-e] pyrimidine derivatives were designed, synthesized, and evaluated for their cytotoxic activities. The in vitro cell growth inhibition assay of the target compounds indicated their selectivity in inhibiting the proliferation of blood tumor cells (K562, U937) and solid tumor cells (HCT116, HT-29). Compound 9b exhibited the highest antiproliferative activities against K562 (IC50 = 5.597 μM) and U937 (IC50 = 3.512 μM). Based on the flow cytometry assays, compound 9b caused obvious induction of cell apoptosis and cell arrest at the S phase. Furthermore, western blot analysis revealed that compound 9b upregulated the expression of Bax, downregulated the levels of Bcl-2, and further activated caspase-3 in K562 cells. Therefore, compound 9b may be a potential anticancer agent that deserves further investigation.

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

The reductive cleavage of picolinic amides

Treatment of picolinic amides with excess zinc in aqueous hydrochloric acid at room temperature affords the corresponding amines in good to excellent yields. The mild reaction conditions exhibit useful functional group tolerance and facilitate the application of the picolinic amide moiety as a protecting group which can be easily introduced and selectively removed.