Conditions | Yield |
---|---|
With hydrogen bromide; bromine; sodium nitrite at 5℃; | 88% |
With hydrogen bromide; bromine; sodium nitrite In water; triethylamine at -20℃; | 88% |
With hydrogen bromide; bromine; sodium nitrite at 0℃; | 80% |
3-methylpyridin-2-ol
2-bromo-3-picoline
Conditions | Yield |
---|---|
With phosphorus tribromide at 190℃; |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With lithium diisopropyl amide 1.) THF, -70 deg C, 4 h, 2.) THF; Yield given. Multistep reaction; |
2,3-dibromopyridine
methyl iodide
A
2-bromo-pyridine
B
2-bromo-3-picoline
Conditions | Yield |
---|---|
Stage #1: 2,3-dibromopyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.183333h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 0.183333h; | A 24 %Chromat. B 48 %Chromat. |
Stage #1: 2,3-dibromopyridine With n-butyllithium In tetrahydrofuran; hexane at -48℃; for 0.183333h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -48℃; for 0.183333h; | A 26 %Chromat. B 19 %Chromat. |
2-bromo-3-picoline
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 100℃; for 3.5h; Suzuki-Miyaura coupling reaction; | 100% |
2-bromo-3-picoline
5-methoxy-2-(N,N-diethylcarboxamido)phenylboronic acid
N,N-diethyl-4-methoxy-2-(3-methylpyridin-2-yl)benzamide
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 5h; Heating / reflux; | 100% |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 2.08333h; | 100% |
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 4h; | 91% |
2-bromo-3-picoline
N-Boc-indole-2-boronic acid
tert-Butyl 2-(3-methyl-2-pyridyl)-1H-indole-1-carboxylate
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane for 18h; Arylation; Suzuki reaction; Heating; | 99% |
2-bromo-3-picoline
Conditions | Yield |
---|---|
With sodium t-butanolate In N,N-dimethyl-formamide at 80℃; for 12h; Sealed tube; | 99% |
With sodium t-butanolate In N,N-dimethyl-formamide at 80℃; | 96% |
With sodium t-butanolate In N,N-dimethyl-formamide at 80℃; for 12h; Sealed tube; Inert atmosphere; | 99 %Spectr. |
Conditions | Yield |
---|---|
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 1-(7-benzofuranyl)-2-di(3,5-di-tert-butyl-4-methoxyphenyl)phosphinenaphthalene In toluene at 80℃; for 3h; Reagent/catalyst; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere; | 99% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 24h; Inert atmosphere; Schlenk technique; Reflux; | 95% |
With 2C32H41O4P*Pd(2+)*2Cl(1-); water In tetrahydrofuran at 60℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere; | 92% |
With tetrakis(triphenylphosphine) palladium(0); 1-chloroisoquinoline; sodium carbonate In ethanol; water; toluene at 120℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; |
2-bromo-3-picoline
1,3,5-tri(pyridin-2-yl)benzene
Conditions | Yield |
---|---|
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium pivalate; sodium carbonate; triphenylphosphine In water at 200℃; for 4h; Inert atmosphere; Microwave irradiation; | 96% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; | 96% |
2-bromo-3-picoline
2-methyl-4-(pyrid-2-yl)but-3-yn-2-ol
3-methyl-2-(pyridin-2'-ylethynyl)pyridine
Conditions | Yield |
---|---|
With copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine; sodium hydroxide In acetonitrile at 76℃; for 23h; Sonogashira coupling; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 12h; | 95% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere; | 65.8% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20 - 70℃; for 6h; |
2-bromo-3-picoline
2-(4-(N,N-dimethylamino)phenyl)-3-methylpyridine
Conditions | Yield |
---|---|
With dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 15h; Negishi cross-coupling reaction; In air; | 94% |
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; toluene at 80℃; for 2h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In water; dimethyl sulfoxide at 23℃; for 16h; Irradiation; | 94% |
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 18h; | 94% |
2-bromo-3-picoline
methanol
carbon monoxide
3-methyl-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine at 80℃; under 2585.81 Torr; for 16h; | 93.6% |
2-bromo-3-picoline
4-Phenyl-1-butyne
3-methyl-2-(4-phenylbut-1-yn-1-yl)pyridine
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 1h; Sonogashira Cross-Coupling; | 93% |
2-bromo-3-picoline
3-(tert-butoxycarbonyl)phenylboronic acid
tert-butyl 3-(3-methylpyridin-2-yl)benzoate
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-picoline With potassium carbonate In water; toluene at 65℃; Inert atmosphere; Stage #2: 3-(tert-butoxycarbonyl)phenylboronic acid With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; toluene for 18h; Inert atmosphere; Reflux; | 92% |
Stage #1: 2-bromo-3-picoline With potassium carbonate In water; toluene at 65℃; for 1h; Stage #2: 3-(tert-butoxycarbonyl)phenylboronic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; toluene at 80℃; for 2h; | 82% |
Stage #1: 2-bromo-3-picoline With potassium carbonate In toluene at 65℃; for 1h; Inert atmosphere; Stage #2: 3-(tert-butoxycarbonyl)phenylboronic acid With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 80℃; for 2h; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-picoline With isopropylmagnesium chloride In tetrahydrofuran; diethyl ether at 0℃; for 3h; Stage #2: Triisopropyl borate In tetrahydrofuran; Dimethyl ether at 20℃; for 1h; | 92% |
2-bromo-3-picoline
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-picoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: With magnesium chloride In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #3: C15H21ClMgN2*LiCl Further stages; | 92% |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-picoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.533333h; Sealed tube; Inert atmosphere; Stage #2: (3-methylpyridin-2-yl)(phenyl)(p-tolyl)sulfonium trifluoromethanesulfonate In tetrahydrofuran; hexane at -78℃; for 2h; Sealed tube; Inert atmosphere; | 92% |
2-bromo-3-picoline
di(1-adamantyl) ketone
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-picoline With n-butyllithium In diethyl ether; pentane at -75℃; for 0.5h; Metallation; Stage #2: di(1-adamantyl) ketone In diethyl ether; pentane at -75 - 0℃; for 2h; Substitution; | 91% |
The 2-Bromo-3-methylpyridine is its IUPAC name about this chemical. With cas registry number of 3430-17-9, it is clear slightly yellow to light brown liquid. This chemical belongs to the categories in blocks; Bromides; Pyridine Series; Indoles and derivatives; Halides; Pyridines derivates; Bromopyridines; Halopyridines; Boronic Acid; C6 Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Brominated heterocyclic series.
Physical properties about this chemical are: (1)ACD/LogP: 1.99; (2)# of Rule of 5 Violations: 0 ; (3)#H bond acceptors: 1; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 0; (6)Index of Refraction: 1.553; (7)Molar Refractivity: 36.85 cm3; (8)Molar Volume: 115.1 cm3; (9)Surface Tension: 40 dyne/cm; (10)Density: 1.494 g/cm3; (11)Flash Point: 84 °C; (12)Enthalpy of Vaporization: 43.32 kJ/mol; (13)Boiling Point: 215.3 °C at 760 mmHg; (14)Vapour Pressure: 0.218 mmHg at 25°C.
Preparation of 2-Bromo-3-methylpyridine: it can be made by 3-methyl-pyridin-2-ylamine using reagents NaNO2, Br2, 48percent HBr. The reaction temperature is 5 ℃. The yield is 88%.
Uses of 2-Bromo-3-methylpyridine: it can be used to made 3,3'-dimethyl-[2,2']bipyridinyl using reagents Ni (Ph3P)2Cl2, Zn, Et4NI, solvent tetrahydrofuran with reaction temperature of 60 ℃. The reaction time needs 3 days with 77% yield.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed and irritating to eyes, respiratory system and skin. Wear suitable protective clothing, gloves and eye/face protection during using it. 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)Canonical SMILES: CC1=C(N=CC=C1)Br;
(2)InChI: InChI=1S/C6H6BrN/c1-5-3-2-4-8-6(5)7/h2-4H,1H3;
(3)InChIKey: PZSISEFPCYMBDL-UHFFFAOYSA-N
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