5-Bromo-2-methyl-3-nitropyridine supplier

Name
5-Bromo-2-methyl-3-nitropyridine
EINECS 200-258-5
CAS No. 911434-05-4
Article Data24
CAS DataBase
Density 1.709 g/cm³
Solubility
Melting Point 38.0 to 42.0 °C
Formula C₆H₅BrN₂O₂
Boiling Point 252.6 °C at 760 mmHg
Molecular Weight 217.022
Flash Point 106.6 °C
Transport Information
Appearance
Safety
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 5-Bromo-2-methyl-3-nitropyridine;5-Bromo-3-nitropicoline;5-Bromo-2-methyl-3-nitrop...;5-Bromo-3-nitro-2-picoline;5-broMo-2-Methyl-3-n;Pyridine,5-broMo-2-Methyl-3-nitro-
PSA 58.71000
LogP 2.58390

Synthetic route

: 911434-04-3
2-(5-bromo-3-nitro-pyridin-2-yl)-malonic acid diethyl ester

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

Conditions

Conditions	Yield
With hydrogenchloride; water for 5h; Heating / reflux;	96%
With hydrogenchloride In water Reflux;	95%
With hydrogenchloride; water for 5h; Reflux;	89.7%

: 67443-38-3
5-bromo-2-chloro-3-nitropyridine

: 105-53-3
diethyl malonate

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

Conditions

Conditions	Yield
Stage #1: 5-bromo-2-chloro-3-nitropyridine; diethyl malonate With sodium hydride In tetrahydrofuran at 20℃; for 3.5h; Stage #2: With hydrogenchloride; water Heating / reflux; Stage #3: With water; sodium carbonate pH=9;	63.3%
Stage #1: 5-bromo-2-chloro-3-nitropyridine; diethyl malonate With sodium hydride In tetrahydrofuran at 20℃; for 3.5h; Stage #2: With hydrogenchloride; water Heating / reflux; Stage #3: With sodium carbonate pH=9;	63.3%
Stage #1: 5-bromo-2-chloro-3-nitropyridine; diethyl malonate With sodium hydride In tetrahydrofuran at 20℃; for 3.5h; Stage #2: With hydrogenchloride; water Heating / reflux; Stage #3: With water; sodium carbonate pH=9;	63.3%
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.333333h; Stage #2: 5-bromo-2-chloro-3-nitropyridine In N,N-dimethyl-formamide; mineral oil at 20 - 40℃; for 1.5h; Stage #3: With hydrogenchloride In water at 100℃; for 13h;
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Stage #2: 5-bromo-2-chloro-3-nitropyridine at 20 - 40℃; for 1.5h;

: 67443-38-3
5-bromo-2-chloro-3-nitropyridine

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere 2: hydrogenchloride / water / 110 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C 1.2: 2 h / 100 °C 2.1: hydrogenchloride; water / 18 h / Reflux 2.2: 0 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 2 h / 100 °C 2.1: hydrogenchloride; water / 18 h / Reflux 2.2: 0 °C View Scheme

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 1229457-88-8
(E)-2-(5-bromo-3-nitropyridin-2-yl)-N,N-dimethylethen-1-amine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 4h;	98%
In N,N-dimethyl-formamide at 90℃; for 4h;	76%
In N,N-dimethyl-formamide at 20 - 90℃; for 7.5h; Large scale;

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide

: N-(6-methyl-5-nitropyridin-3-yl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide

Conditions

Conditions	Yield
With potassium carbonate; rac-diaminocyclohexane; copper(I) bromide In toluene at 90 - 100℃; Reagent/catalyst; Solvent; Inert atmosphere;	96.3%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 1227628-14-9
2-(5-bromo-3-nitropyridin-2-yl)-N,N-dimethylethenamine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 4.25h; Inert atmosphere;	95.2%
In N,N-dimethyl-formamide at 90℃; for 0.25h;	95.2%
In N,N-dimethyl-formamide at 10℃; for 5h;
In N,N-dimethyl-formamide at 100℃; for 1h;

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1229457-95-7
tert-butyl 4-[4-(6-methyl-5-nitropyridin-3-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 5-bromo-2-methyl-3-nitropyridine; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 20℃; for 0.333333h; Stage #2: tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate With potassium carbonate In 1,2-dimethoxyethane; isopropyl alcohol at 20 - 85℃;	95%

: 603143-27-7
(4,4,5,5-tetramethyl-2-[4-(methylsulfonyl)phenyl])-1,3,2-dioxaborolane

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1353715-51-1
2-methyl-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 12h; Inert atmosphere;	94%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1066-54-2
trimethylsilylacetylene

: 1228962-69-3
2-methyl-3-nitro-5-[(trimethylsilyl)ethynyl]pyridine

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 80℃; for 4h;	91%

: 7223-38-3
N,N-Dimethylpropargylamin

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1286218-46-9
N,N-dimethyl-3-(6-methyl-5-nitropyridin-3-yl)prop-2-yn-1-amine

Conditions

Conditions	Yield
With diethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 15h; Product distribution / selectivity;	91%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 20℃; Darkness; Reflux;	91%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 914358-73-9
5-bromo-2-methylpyridin-3-ylamine

Conditions

Conditions	Yield
With hydrogenchloride; iron In methanol; water for 2h; Reflux;	90%
With iron; ammonium chloride In ethanol; water at 90℃; for 0.666667h;	90%
With iron; ammonium chloride In ethanol; water at 90℃; for 0.666667h;	90%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 92136-39-5
N-tert-Butoxycarbonyl-1-amino-3-propyne

: 1228962-84-2
tert-butyl [3-(6-methyl-5-nitropyridin-3-yl)prop-2-yn-1-yl]carbamate

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 70℃; for 2.5h; Inert atmosphere;	79%

: 109-01-3
1-methyl-piperazine

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1228962-94-4
1-methyl-4-(6-methyl-5-nitropyridin-3-yl)piperazine

Conditions

Conditions	Yield
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 150℃; for 22h; sealed tube; Inert atmosphere;	71%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: C16H27BO

: 5-(2-(cyclohex-3-en-1-yl)ethyl)-2-methyl-3-nitropyridine

Conditions

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In water at 45℃; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	67%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 73183-34-3
bis(pinacol)diborane

: 1353715-51-1
2-methyl-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Conditions

Conditions	Yield
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 100℃; for 1.5h; Microwave irradiation;	66%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 6h; Inert atmosphere;

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: C14H27BO2

: 5-(2-(t-butoxy)ethyl)-2-methyl-3-nitropyridine

Conditions

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In water at 45℃; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	64%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1228962-22-8
tert-butyl 3,3-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-dihydropyridine-1-carboxylate

: 1228962-23-9
tert-butyl 3',3',6-trimethyl-5-nitro-3',6'-dihydro-3,4'-bipyridine-1'(2'H)-carboxylate

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 24h; Inert atmosphere;	60%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 944937-53-5
6-bromo-1H-pyrrolo[3,2-b]pyrridine

Conditions

Conditions	Yield
Stage #1: 5-bromo-2-methyl-3-nitropyridine; N,N-dimethyl-formamide dimethyl acetal In N,N-dimethyl-formamide at 100℃; for 1h; Stage #2: With iron; acetic acid at 100℃; for 20h; Inert atmosphere;	60%

: 454482-11-2
1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl )-1,2,3,6-tetrahydropyridine

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: C12H15N3O2

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; Inert atmosphere;	56%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 159635-49-1
tert-butyl 4-methylidenepiperidine-1-carboxylate

: tert-butyl 4-[(6-methyl-5-nitro-3-pyridyl)methylene]piperidine-1-carboxylate

Conditions

Conditions	Yield
With potassium acetate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 100℃; Sealed tube;	42%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1352492-38-6
3-ethynyloxetan-3-ol

: 3-[2-(6-methyl-5-nitro-3-pyridyl)ethynyl]oxetan-3-ol

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 20℃;	40%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1826-67-1
vinyl magnesium bromide

: 4-bromo-7-methyl-1H-pyrrolo[2,3-c]pyridine

Conditions

Conditions	Yield
In tetrahydrofuran at -50 - -40℃; for 0.5h; Inert atmosphere;	36.6%
In tetrahydrofuran at -50 - -40℃; for 0.5h; Inert atmosphere;	36.6%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1413732-47-4
(2,2'-bipyride-kN1,kN1')(1,1,1-trifluoromethanethiolato-kS)-copper

: 2-methyl-3-nitro-5-[(trifluoromethyl)thio]pyridine

Conditions

Conditions	Yield
In 1,4-dioxane at 110℃; for 15h; Inert atmosphere;	23%

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 954240-89-2
5-bromo-3-nitropicolinic acid

Conditions

Conditions	Yield
With potassium permanganate In acetonitrile at 80 - 100℃;	2.4%

: 857265-74-8
5-ethynylpyrimidine-2-amine

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 911434-06-5
5-(6-methyl-5-nitro-pyridin-3-ylethynyl)-pyrimidin-2-ylamine

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 60℃; for 3h;

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1112980-38-7
N-(6-(5-(4-methoxyphenylsulfonamido)-6-methylpyridin-3-yl)benzo[d]thiazol-2-yl)acetamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: water; iron; acetic acid / 1.25 h / 20 °C / Inert atmosphere; Cooling 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,2-dimethoxyethane; water / 1.33 h / 100 °C / Inert atmosphere 3: pyridine; dmap / tetrahydrofuran / 6 h / 65 °C / Inert atmosphere View Scheme

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1150617-54-1
6-bromo-1H-pyrazolo[4,3-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride; iron / ethanol; water / 40 °C / Reflux 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: acetic anhydride; potassium acetate; acetic acid / chloroform / 0.25 h / 20 °C 3.2: 40 - 60 °C 3.3: 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride; iron / water; industrial methylated spirit / 2 h / Reflux 2: triethylamine / dichloromethane / 90 h / 20 °C 3: acetic anhydride; potassium acetate; isopentyl nitrite / chloroform; acetic acid / 20 - 60 °C View Scheme
Multi-step reaction with 4 steps 1.1: acetic acid; iron / 2 h / Reflux 2.1: triethylamine / dichloromethane / 18 h 2.2: 1 h 3.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 3 h / Reflux 4.1: potassium carbonate; methanol / 1 h / Reflux View Scheme

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1301214-71-0
N-(5-bromo-2-methyl-pyridin-3-yl)-acetamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; iron / ethanol; water / 40 °C / Reflux 2: triethylamine / dichloromethane / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride; iron / water; industrial methylated spirit / 2 h / Reflux 2: triethylamine / dichloromethane / 90 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: acetic acid; iron / 2 h / Reflux 2.1: triethylamine / dichloromethane / 18 h 2.2: 1 h View Scheme

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1301214-72-1
1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride; iron / ethanol; water / 40 °C / Reflux 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: acetic anhydride; potassium acetate; acetic acid / chloroform / 0.25 h / 20 °C 3.2: 40 - 60 °C 3.3: 0 - 20 °C 4.1: triethylamine / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium dichloride / acetonitrile / 18 h / 100 °C / 15001.5 Torr View Scheme
Multi-step reaction with 4 steps 1: hydrogenchloride; iron / water; industrial methylated spirit / 2 h / Reflux 2: triethylamine / dichloromethane / 90 h / 20 °C 3: acetic anhydride; potassium acetate; isopentyl nitrite / chloroform; acetic acid / 20 - 60 °C 4: triethylamine / (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium dichloride / acetonitrile / 18 h / 100 °C / 15001.5 Torr View Scheme
Multi-step reaction with 4 steps 1: iron; ammonium chloride / water; ethanol / 0.17 h / 90 °C 2: acetic acid / 20 °C 3: acetic anhydride; isopentyl nitrite; potassium acetate / toluene / 90 °C / Inert atmosphere 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 100 °C / 7600.51 Torr View Scheme

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1256807-59-6
1H-pyrazolo[4,3-b] pyridine-6-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogenchloride; iron / ethanol; water / 40 °C / Reflux 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: acetic anhydride; potassium acetate; acetic acid / chloroform / 0.25 h / 20 °C 3.2: 40 - 60 °C 3.3: 0 - 20 °C 4.1: triethylamine / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium dichloride / acetonitrile / 18 h / 100 °C / 15001.5 Torr 5.1: sodium hydroxide; water / methanol / 0 - 20 °C 5.2: pH 5 - 6 View Scheme
Multi-step reaction with 5 steps 1.1: hydrogenchloride; iron / water; industrial methylated spirit / 2 h / Reflux 2.1: triethylamine / dichloromethane / 90 h / 20 °C 3.1: acetic anhydride; potassium acetate; isopentyl nitrite / chloroform; acetic acid / 20 - 60 °C 4.1: triethylamine / (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium dichloride / acetonitrile / 18 h / 100 °C / 15001.5 Torr 5.1: sodium hydroxide; water / methanol / 18 h / 20 °C 5.2: pH 5 - 6 View Scheme
Multi-step reaction with 5 steps 1: iron; ammonium chloride / water; ethanol / 0.17 h / 90 °C 2: acetic acid / 20 °C 3: acetic anhydride; isopentyl nitrite; potassium acetate / toluene / 90 °C / Inert atmosphere 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 100 °C / 7600.51 Torr 5: water; sodium hydroxide / 20 °C View Scheme

5-Bromo-2-methyl-3-nitropyridine Specification

The 5-Bromo-2-methyl-3-nitropyridine, with the CAS registry number 911434-05-4, is also called pyridine, 5-bromo-2-methyl-3-nitro-. It should be stored at dry and cool environment. And the molecular formula of the chemical is C₆H₅BrN₂O₂.

The characteristics of 5-Bromo-2-methyl-3-nitropyridine are as followings: (1)ACD/LogP: 1.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.85; (4)ACD/LogD (pH 7.4): 1.85; (5)#H bond acceptors: 4; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 1; (8)Polar Surface Area: 58.71 Å²; (9)Index of Refraction: 1.599; (10)Molar Refractivity: 43.4 cm³; (11)Molar Volume: 126.9 cm³; (12)Polarizability: 17.2×10^-24cm³; (13)Surface Tension: 54.5 dyne/cm; (14)Density: 1.709 g/cm³; (15)Flash Point: 106.6 °C; (16)Enthalpy of Vaporization: 47.02 kJ/mol; (17)Boiling Point: 252.6 °C at 760 mmHg; (18)Vapour Pressure: 0.0305 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Cc1c(cc(cn1)Br)[N+](=O)[O-]
(2)InChI: InChI=1/C6H5BrN2O2/c1-4-6(9(10)11)2-5(7)3-8-4/h2-3H,1H3
(3)InChIKey: FZZLWWNOYMHSIS-UHFFFAOYAD

Product Name

5-Bromo-2-methyl-3-nitropyridine

Synthetic route

5-Bromo-2-methyl-3-nitropyridine Specification

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