Conditions | Yield |
---|---|
Stage #1: 2-Amino-6-methylpyridine With hydrogen bromide; bromine at -10 - -5℃; for 1.5h; Stage #2: With sodium nitrite In water at -10 - -5℃; for 1.5h; Stage #3: With sodium hydroxide In water at -10℃; | 95% |
Stage #1: 2-Amino-6-methylpyridine With hydrogen bromide at 60 - 62℃; for 1h; Stage #2: With bromine at -5 - -3℃; for 3h; Stage #3: With sodium nitrite In water for 3h; Temperature; | 93.1% |
Stage #1: 2-Amino-6-methylpyridine With bromine at -20℃; for 1.5h; Stage #2: With sodium nitrite at -20 - 15℃; Stage #3: With sodium hydroxide at -10 - 20℃; Further stages.; | 90% |
Conditions | Yield |
---|---|
In diethyl ether at -25 - 0℃; for 4h; | 59% |
6-chloro-2-picoline
2-bromo-6-methylpyridine
Conditions | Yield |
---|---|
With trimethylsilyl bromide In various solvent(s) for 100h; Heating; | 47% |
Conditions | Yield |
---|---|
With phosphorus(V) oxybromide |
6-hydroxy-2-methylpyridine
A
2-bromo-6-methylpyridine
B
2,3,5-tribromo-6-methyl-pyridine
Conditions | Yield |
---|---|
With phosphorus pentabromide at 160℃; |
Conditions | Yield |
---|---|
at 160℃; |
2-Amino-6-methylpyridine
hydrogen bromide
A
2-bromo-6-methylpyridine
B
3,5-dibromo-2-hydroxy-6-methylpyridine
6-hydroxy-2-methylpyridine
phosphorus pentabromide
A
2-bromo-6-methylpyridine
Conditions | Yield |
---|---|
at 160℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaNH2; xylene 2: aqueous hydrobromic acid / Behandeln mit Brom und mit wss. Natriumnitrit-Loesung View Scheme |
Conditions | Yield |
---|---|
Stage #1: 2,6-Dibromopyridine With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1.52778E-05h; Stage #2: methyl iodide In tetrahydrofuran; hexane at 0℃; for 0.0025h; | 94 %Chromat. |
Stage #1: 2,6-Dibromopyridine With n-butyllithium In hexane at 0℃; for 1.52778E-05h; Stage #2: methyl iodide In tetrahydrofuran; hexane at 0℃; for 0.0025h; | 94 %Chromat. |
Conditions | Yield |
---|---|
Stage #1: 2,6-Dibromopyridine With n-butyllithium In diethyl ether Stage #2: dimethyl sulfate at -78 - 20℃; for 16h; |
Conditions | Yield |
---|---|
With tert-butylhypochlorite; dichloromethane; oxygen; sodium hydrogencarbonate at 70℃; for 30h; Green chemistry; | 35 %Spectr. |
2-bromo-6-methylpyridine
1-Heptyne
2-(hept-1-yn-1-yl)-6-methylpyridine
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 60℃; for 1.5h; | 100% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux; | 100% |
With potassium phosphate; palladium diacetate In ethylene glycol at 80℃; Inert atmosphere; | 99% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol at 100℃; for 15h; Inert atmosphere; | 99% |
2-bromo-6-methylpyridine
tributyltin chloride
2-methyl-6-(tributylstannyl)pyridine
Conditions | Yield |
---|---|
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h; Schlenk technique; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran; hexane at 20℃; Schlenk technique; Inert atmosphere; | 100% |
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere; | 100% |
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium In tetrahydrofuran at -78℃; for 3h; Stage #2: tributyltin chloride In tetrahydrofuran at 20℃; | 96.75% |
2-bromo-6-methylpyridine
Conditions | Yield |
---|---|
With fluorosilicic acid; water In methanol at 20℃; | 100% |
2-bromo-6-methylpyridine
Diethyl carbonate
(6-bromo-pyridin-2-yl)-acetic acid ethyl ester
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran at -60 - -40℃; for 16h; | 100% |
Stage #1: 2-bromo-6-methylpyridine With lithium diisopropyl amide In tetrahydrofuran at -70℃; for 0.5h; Stage #2: Diethyl carbonate In tetrahydrofuran at -70 - 20℃; for 4h; | 77% |
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Diethyl carbonate In tetrahydrofuran; hexane at -78 - 20℃; | 55% |
Stage #1: 2-bromo-6-methylpyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: Diethyl carbonate In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 53% |
Stage #1: 2-bromo-6-methylpyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: Diethyl carbonate In tetrahydrofuran at -78℃; Inert atmosphere; | 35% |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Stage #2: 3,3-dimethyl-butan-2-one In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
With Ni(acetylacetate)2; 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclo-hexadiene In toluene at 80℃; for 18h; | 99% |
nickel dibromide In N,N-dimethyl-formamide at 20℃; Electrochemical reaction; constant current intensity 200 mA; | 98% |
Stage #1: 2-bromo-6-methylpyridine With lithium chloride; nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 0.0833333h; Stage #2: With iodine; acetic acid In N,N-dimethyl-formamide at 50℃; for 0.333333h; Stage #3: 2-bromo-6-methylpyridine In N,N-dimethyl-formamide at 80℃; for 24h; | 98% |
2-bromo-6-methylpyridine
4-(diphenylamino)phenyl boronic acid
N,N-diphenyl-4-(6-methylpyridinyl-2-yl)aniline
Conditions | Yield |
---|---|
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; isopropyl alcohol at 80℃; for 0.133333h; Suzuki reaction; | 99% |
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.0666667h; Suzuki Coupling; | 98% |
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; Suzuki Coupling; | |
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 1h; Suzuki Coupling; |
4-(carbazol-9-yl)phenylboronic acid
2-bromo-6-methylpyridine
9-(4-(6-methylpyridin-2-yl)phenyl)-9H-carbazole
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.0833333h; Suzuki Coupling; | 99% |
2-bromo-6-methylpyridine
4-Chlorophenylboronic acid
2-(4-chlorophenyl)-6-methylpyridine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 70 - 90℃; for 18h; Inert atmosphere; | 99% |
With potassium phosphate; palladium diacetate In ethylene glycol at 80℃; Inert atmosphere; | 87% |
2-bromo-6-methylpyridine
3-phenylsydnone
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; XPhos In N,N-dimethyl-formamide at 80 - 120℃; for 16h; Inert atmosphere; | 99% |
2-bromo-6-methylpyridine
n-butyllithium
Triisopropyl borate
Conditions | Yield |
---|---|
at -78℃; | 99% |
2-bromo-6-methylpyridine
6,6'-dimethyl-2,2'-thiodipyridine
Conditions | Yield |
---|---|
With thiourea In ethanol at 78℃; for 36h; Inert atmosphere; | 99% |
With thiourea In ethanol for 36h; Inert atmosphere; Schlenk technique; Reflux; | 93% |
2-bromo-6-methylpyridine
tributyl(thien-2-yl)stannane
2-(thiophen-2'-yl)-6-methylpyridine
Conditions | Yield |
---|---|
With copper(l) iodide; tri-tert-butyl phosphine; cesium fluoride; palladium dichloride In N,N-dimethyl-formamide at 45℃; for 15h; Stille reaction; | 98% |
With cesium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 100℃; for 36h; Stille coupling; | 96% |
2-bromo-6-methylpyridine
trimethyltin(IV)chloride
2-methyl-6-(trimethylstannyl)pyridine
Conditions | Yield |
---|---|
With n-BuLi In tetrahydrofuran under N2 atm. soln. 2-bromo-6-methylpyridine in THF was cooled to -78°C, treated dropwise with soln. n-BuLi in hexane, stirred for 30 min, soln. Me3SnCl in THF was added and stirred for 1 h, warmed to room temp.; react. mixt. was quenched with aq. NH4Cl, extd. with Et2O, dried over Na2SO4, solvent was removed in vacuo; elem. anal.; | 97% |
With BuLi In tetrahydrofuran dropwise addn. of pyridine in THF to BuLi in THF at -78°C, stirred for 1 h, addn. of Me3SnCl in THF at -78°C, allowed to warm to room temp.; removal of solvent under reduced pressure, addn. of methylcyclohexane, filtered off, removal of solvent, distn.; | 58% |
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium In diethyl ether; hexane at -78℃; for 1.16667h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; diethyl ether; hexane at -78 - 20℃; for 3h; | |
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium In diethyl ether; hexane at -78℃; for 1.16667h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; diethyl ether; hexane at -78 - 20℃; for 3h; Inert atmosphere; | |
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium In tetrahydrofuran; hexane at -65℃; for 3.5h; Irradiation; Inert atmosphere; Schlenk technique; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -65 - 20℃; for 1h; Inert atmosphere; Schlenk technique; |
NH-pyrazole
2-bromo-6-methylpyridine
2-methyl-6-(1H-pyrazole-1-yl)pyridine
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; | 97% |
With potassium tert-butylate In dimethyl sulfoxide at 120℃; Inert atmosphere; Schlenk technique; | 90% |
2-bromo-6-methylpyridine
methyl 2-[(tert-butoxycarbonyl)amino]acrylate
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; | 97% |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-6-methylpyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Stage #2: N-Benzylidenemethylamine In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h; | 97% |
2-bromo-6-methylpyridine
2-ethynylpyridine
2-Methyl-6-pyridin-2-ylethynyl-pyridine
Conditions | Yield |
---|---|
With copper(l) iodide; diisopropylamine; tetrakis(triphenylphosphine) palladium(0) In toluene at 20℃; for 12h; Sonogashira coupling; | 96% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; Suzuki-Miyaura coupling; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With copper(I) oxide; potassium phosphate; N1,N2-bis(furan-2-ylmethyl)oxalamide In dimethyl sulfoxide at 120℃; for 36h; | 96% |
Conditions | Yield |
---|---|
With copper(l) iodide; N1, N2-diphenethyloxalamide; sodium t-butanolate In 1,4-dioxane for 24h; Schlenk technique; Inert atmosphere; Molecular sieve; Heating; | 96% |
2-bromo-6-methylpyridine
1-t-Butoxycarbonylpiperazine
tert-butyl-4-(6-methylpyridin-2-yl)piperazine-1-carboxylate
Conditions | Yield |
---|---|
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 70℃; for 1.5h; | 95% |
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 70℃; for 1.5h; | 95% |
2-bromo-6-methylpyridine
N-(2,4,6-trimethylphenyl)imidazole
1-mesityl-3-(6-methyl-2-pyridyl)imidazolium bromide
Conditions | Yield |
---|---|
at 150℃; Inert atmosphere; | 95% |
at 150℃; for 72h; | 45% |
2-bromo-6-methylpyridine
2-Methoxyphenylboronic acid
2-(2-methoxyphenyl)-6-methylpyridine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethanol; water at 80℃; Suzuki-Miyaura Coupling; | 95% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 90℃; Inert atmosphere; | 71% |
2-bromo-6-methylpyridine
diphenyl (prop-2-yn-1-yl)phosphine oxide
Conditions | Yield |
---|---|
With sodium azide; bromotris(triphenylphosphine)copper(I) In water; dimethyl sulfoxide at 110℃; under 760.051 Torr; for 0.183333h; Huisgen Cycloaddition; Microwave irradiation; Green chemistry; regioselective reaction; | 95% |
2-bromo-6-methylpyridine
(E)-2-(4-methoxyphenyl)vinylboronic acid
C15H15NO
Conditions | Yield |
---|---|
With potassium phosphate In ethanol; water at 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere; | 95% |
2-bromo-6-methylpyridine
2-bromo-6-methylpyridine N-oxide
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid at 90℃; for 24h; | 94% |
With dihydrogen peroxide; acetic acid at 90℃; for 24h; | 94% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane | 90% |
2-bromo-6-methylpyridine
tris(6-methylpyridin-2-yl)amine
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; lithium amide In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere; chemoselective reaction; | 94% |
The 2-Bromo-6-Methyl pyridine is an organic compound with the formula C6H6BrN. The IUPAC name of this chemical is 2-bromo-6-methylpyridine. With the CAS registry number 5315-25-3, it is also named as Pyridine, 2-bromo-6-methyl-. The product's categories are Compounds of Pyridine; Blocks; Bromides; Pyridines; Pyridine; Pyridine Derivative; Halides; Heterocycles; Pyridines, Pyrimidines, Purines and Pteredines; Bromopyridines; Halopyridines; Boronic Acid; C6Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks. Besides, it is light yellow liquid, which should be stored in a dark cool and dry place.
Physical properties about 2-Bromo-6-Methyl pyridine are: (1)ACD/LogP: 1.99; (2)ACD/LogD (pH 5.5): 1.99; (3)ACD/LogD (pH 7.4): 1.99; (4)ACD/BCF (pH 5.5): 19.2; (5)ACD/BCF (pH 7.4): 19.2; (6)ACD/KOC (pH 5.5): 288.5; (7)ACD/KOC (pH 7.4): 288.53; (8)#H bond acceptors: 1; (9)Polar Surface Area: 12.89 Å2; (10)Index of Refraction: 1.553; (11)Molar Refractivity: 36.85 cm3; (12)Molar Volume: 115.1 cm3; (13)Polarizability: 14.61×10-24cm3; (14)Surface Tension: 40 dyne/cm; (15)Density: 1.494 g/cm3; (16)Flash Point: 74.4 °C; (17)Enthalpy of Vaporization: 41.79 kJ/mol; (18)Boiling Point: 199.5 °C at 760 mmHg; (19)Vapour Pressure: 0.482 mmHg at 25°C.
Preparation: this chemical can be prepared by 6-methyl-pyridin-2-ylamine. This reaction will need reagent HBr and NaNO2. The reaction temperature is -20 °C.
Uses of 2-Bromo-6-Methyl pyridine: it can be used to produce 6,6'-dimethyl-[2,2']bipyridinyl. It will need reagent Ni[P(C6H5)3]4. The yield is about 84%.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. 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)SMILES: Cc1cccc(n1)Br
(2)InChI: InChI=1/C6H6BrN/c1-5-3-2-4-6(7)8-5/h2-4H,1H3
(3)InChIKey: SOHDPICLICFSOP-UHFFFAOYAL
(4)Std. InChI: InChI=1S/C6H6BrN/c1-5-3-2-4-6(7)8-5/h2-4H,1H3
(5)Std. InChIKey: SOHDPICLICFSOP-UHFFFAOYSA-N
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