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2-(2-Amino-5-bromobenzoyl)pyridine
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Name

2-(2-Amino-5-bromobenzoyl)pyridine

 EINECS 216-352-5
CAS No. 1563-56-0 Density 1.546 g/cm3
PSA 55.98000 LogP 3.23850
Solubility N/A Melting Point 98-100oC
Formula C12H9BrN2O Boiling Point 451.2 °C at 760 mmHg
Molecular Weight 277.12 Flash Point 226.7 °C
Transport Information N/A Appearance Yellow solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 1563-56-0 (2-(2-AMINO-5-BROMOBENZOYL) PYRIDINE) Hazard Symbols N/A
Synonyms

Ketone,2-amino-5-bromophenyl 2-pyridyl (7CI,8CI);2-(5-Bromo-2-aminobenzoyl)pyridine;2-Amino-5-bromophenyl 2-pyridyl ketone;2-Amino-5-bromophenyl-2-pyridylmethanone;

Article Data 22

2-(2-Amino-5-bromobenzoyl)pyridine Synthetic route

162271-31-0

2-(5-bromo-2-hydroxybenzoyl)pyridine

1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Stage #1: 2-(5-bromo-2-hydroxybenzoyl)pyridine With 2-bromo-2-methylpropanamide; sodium hydroxide In N,N-dimethyl acetamide at 20 - 50℃; for 4h;
Stage #2: With water for 4h; Reflux;		95.6%
109-04-6

2-bromo-pyridine

5794-88-7

5-Bromo-2-aminobenzoic acid

1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Stage #1: 2-bromo-pyridine; n-butyllithium In diethyl ether; hexane at -40℃; for 1.5h;
Stage #2: 5-Bromo-2-aminobenzoic acid In tetrahydrofuran; diethyl ether; hexane at 0℃; for 2h;
Stage #3: With hydrogenchloride; sodium hydroxide; chloro-trimethyl-silane more than 3 stages;		89.3%
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -40℃;
Stage #2: 5-Bromo-2-aminobenzoic acid In tetrahydrofuran at -40 - 0℃; for 2h;
Stage #3: With chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 0.5h;		62.7%
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -40℃; for 1.25h;
Stage #2: 5-Bromo-2-aminobenzoic acid In tetrahydrofuran at 0℃; for 2h;		62.7%
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -40℃; for 1h; Inert atmosphere;
Stage #2: 5-Bromo-2-aminobenzoic acid In tetrahydrofuran at 0 - 10℃; for 3h; Inert atmosphere;		50.7%
5794-88-7

5-Bromo-2-aminobenzoic acid

1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran at -40℃;
Stage #2: 5-Bromo-2-aminobenzoic acid In tetrahydrofuran at 0℃;		58%
1812-30-2

bromazepam

1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
With intestinal microflora (human) In N,N-dimethyl-formamide at 37℃; for 5h;
With acid
With hydrogenchloride In methanol; water for 3h; Reagent/catalyst; Darkness; Reflux;
1812-30-2

bromazepam

A

1563-56-0

2-amino-5-bromobenzoyl pyridine

B

56-40-6

glycine

Conditions
ConditionsYield
With hydrogenchloride at 25℃; Rate constant; Mechanism; also in micellar system;

C24H17Br2N5

1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
With hydrogenchloride at 90℃; for 1h;

4‑bromo‑2‑(bromomethyl)‑1‑((2‑methoxyethoxy)methoxy)benzene

1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: magnesium; triethylamine / tetrahydrofuran / 20 °C
1.2: 20 h / pH 1 / Reflux
1.3: pH 1
2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 6 h / 75 °C / Inert atmosphere
3.1: tert.-butylhydroperoxide; iodine; pyridine / water / 6 h / 80 °C
4.1: titanium tetrachloride / dichloromethane / 4 h / 20 °C
5.1: sodium hydroxide; 2-bromo-2-methylpropanamide / N,N-dimethyl acetamide / 4 h / 20 - 50 °C
5.2: 4 h / Reflux
View Scheme

5-bromo-2-(((2-methoxyethoxy)methoxy)benzyl)boronic acid

1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 6 h / 75 °C / Inert atmosphere
2.1: tert.-butylhydroperoxide; iodine; pyridine / water / 6 h / 80 °C
3.1: titanium tetrachloride / dichloromethane / 4 h / 20 °C
4.1: sodium hydroxide; 2-bromo-2-methylpropanamide / N,N-dimethyl acetamide / 4 h / 20 - 50 °C
4.2: 4 h / Reflux
View Scheme

2-(5-bromo-2-(((2-methoxyethoxy)methoxy)benzyl)pyridine)

1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tert.-butylhydroperoxide; iodine; pyridine / water / 6 h / 80 °C
2.1: titanium tetrachloride / dichloromethane / 4 h / 20 °C
3.1: sodium hydroxide; 2-bromo-2-methylpropanamide / N,N-dimethyl acetamide / 4 h / 20 - 50 °C
3.2: 4 h / Reflux
View Scheme
5532-69-4

4-bromo-2-(hydroxymethyl)phenol

1563-56-0

2-amino-5-bromobenzoyl pyridine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine / dichloromethane / 6 h / 25 °C
2.1: magnesium; triethylamine / tetrahydrofuran / 20 °C
2.2: 20 h / pH 1 / Reflux
2.3: pH 1
3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 6 h / 75 °C / Inert atmosphere
4.1: tert.-butylhydroperoxide; iodine; pyridine / water / 6 h / 80 °C
5.1: titanium tetrachloride / dichloromethane / 4 h / 20 °C
6.1: sodium hydroxide; 2-bromo-2-methylpropanamide / N,N-dimethyl acetamide / 4 h / 20 - 50 °C
6.2: 4 h / Reflux
View Scheme

2-(2-Amino-5-bromobenzoyl)pyridine Specification

The Methanone,(2-amino-5-bromophenyl)-2-pyridinyl- is an organic compound with the formula C12H9BrN2O. The systematic name of this chemical is (2-Amino-5-bromophenyl)(pyridin-2-yl)methanone. With the CAS registry number 1563-56-0, it is also named as 2-Amino-5-bromobenzoylpyridine. The product's category is Intermediate of Bromazepam. Besides, its molecular weight is 277.12.

Physical properties about Methanone,(2-amino-5-bromophenyl)-2-pyridinyl- are: (1)ACD/LogP: 2.51; (2)ACD/LogD (pH 5.5): 2.51; (3)ACD/LogD (pH 7.4): 2.51; (4)ACD/BCF (pH 5.5): 47.64; (5)ACD/BCF (pH 7.4): 47.64; (6)ACD/KOC (pH 5.5): 552.99; (7)ACD/KOC (pH 7.4): 553; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 33.2 Å2; (12)Index of Refraction: 1.658; (13)Molar Refractivity: 66.06 cm3; (14)Molar Volume: 179.2 cm3; (15)Polarizability: 26.18×10-24 cm3; (16)Surface Tension: 59.3 dyne/cm; (17)Density: 1.546 g/cm3; (18)Flash Point: 226.7 °C; (19)Enthalpy of Vaporization: 71.02 kJ/mol; (20)Boiling Point: 451.2 °C at 760 mmHg; (21)Vapour Pressure: 2.48E-08 mmHg at 25 °C. 

Uses of Methanone,(2-amino-5-bromophenyl)-2-pyridinyl-: it can be used to produce 2-Amino-5-bromobenzoylpyridine. It will need reagent dicyclohexylcarbodiimide and solvent CH2Cl2 with reaction time of 5 days. The yield is about 76.5%.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)InChI: InChI=1/C12H9BrN2O/c13-8-4-5-10(14)9(7-8)12(16)11-3-1-2-6-15-11/h1-7H,14H2
(2)InChIKey: KHVZPFKJBLTYCC-UHFFFAOYAI
(3)Std. InChI: InChI=1S/C12H9BrN2O/c13-8-4-5-10(14)9(7-8)12(16)11-3-1-2-6-15-11/h1-7H,14H2
(4)Std. InChIKey: KHVZPFKJBLTYCC-UHFFFAOYSA-N

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