Conditions | Yield |
---|---|
Stage #1: 3-amino-4-methylpyridine With hydrogen bromide; bromine at -5℃; Stage #2: With sodium nitrite In water at 0℃; Stage #3: With sodium hydroxide In water at 0 - 20℃; for 0.5h; pH=9; | 95% |
Stage #1: 3-amino-4-methylpyridine With hydrogen bromide; bromine at -5℃; Stage #2: With sodium nitrite at 0℃; Stage #3: With sodium hydroxide at 20℃; for 0.5h; pH=9; |
Conditions | Yield |
---|---|
Stage #1: picoline With aluminum (III) chloride; potassium bromide at 20℃; for 1h; Inert atmosphere; Stage #2: With bromine at 120℃; for 27h; Inert atmosphere; | 57% |
With aluminum (III) chloride; bromine at 95 - 105℃; for 43h; Inert atmosphere; | 49% |
Stage #1: picoline With aluminum (III) chloride; bromine at 95 - 100℃; for 22h; Stage #2: With sodium carbonate In water | 19% |
With hydrogenchloride; sodium hydroxide; bromine; aluminium trichloride In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; Petroleum ether | |
Stage #1: picoline With aluminum (III) chloride at -5℃; for 1h; Stage #2: With bromine at 100℃; for 44h; |
3-Bromopyridine
lithium diisopropyl amide
methyl iodide
A
4-bromopyridin
B
4-bromo-3-methylpyridine
C
3-Bromo-4-methylpyridin
Conditions | Yield |
---|---|
In tetrahydrofuran at -60℃; Product distribution; Mechanism; temp. change; |
3-Bromopyridine
methyl iodide
A
4-bromo-3-methylpyridine
B
3-Bromo-4-methylpyridin
Conditions | Yield |
---|---|
THF, -60 -> -55.deg C, 1) 15 min, 2) 45 min; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
THF, -60.deg C, 1) 15 min, 2) 45 min; Yield given. Multistep reaction; |
3-Bromo-4-methyl-4H-pyridine-1-carboxylic acid phenyl ester
3-Bromo-4-methylpyridin
Conditions | Yield |
---|---|
With o-tetrachloroquinone In acetic acid for 8h; Ambient temperature; Yield given; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) CuI, (CH3)2S / 1.) THF, -20 deg C, 5 min, 2.) THF, a) -20 deg C, 15 min, b) RT, 15 min 2: o-chloranil / acetic acid / 8 h / Ambient temperature View Scheme |
3-Bromo-4-methylpyridin
2,4-dimethoxypyrimidin-5-ylboronic acid
5-(4-methyl-pyridin-3-yl)-2,4-dimethoxy-pyrimidine
Conditions | Yield |
---|---|
With sodium carbonate; palladium diacetate; triphenylphosphine In propan-1-ol for 3h; Suzuki Coupling; Heating / reflux; | 100% |
3-Bromo-4-methylpyridin
Diethyl carbonate
ethyl 2-(3-bromopyridin-4-yl)acetate
Conditions | Yield |
---|---|
Stage #1: 3-Bromo-4-methylpyridin With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 2.5h; Stage #2: Diethyl carbonate In tetrahydrofuran for 12h; | 100% |
Stage #1: 3-Bromo-4-methylpyridin; Diethyl carbonate With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 5h; Stage #2: With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 2h; | 91% |
With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; | 68.2% |
Stage #1: 3-Bromo-4-methylpyridin With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; Stage #2: Diethyl carbonate In tetrahydrofuran at 20℃; | 63% |
2-formyl-4,5-(methylenedioxy)benzeneboronic acid
3-Bromo-4-methylpyridin
6-(4-methyl-pyridin-3-yl)-benzo[1,3]dioxole-5-carbaldehyde
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; water; toluene at 90℃; for 15h; Suzuki coupling; | 98% |
benzo[b]thiophene-2-boronic acid
3-Bromo-4-methylpyridin
3-(benzo[b]thiophen-2-yl)-4-methylpyridine
Conditions | Yield |
---|---|
With C43H37ClFeNiP2*C4H8O; potassium carbonate In tetrahydrofuran; acetonitrile at 50℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; | 97% |
thiophene boronic acid
3-Bromo-4-methylpyridin
4-methyl-3-(thiophen-2-yl)pyridine
Conditions | Yield |
---|---|
With potassium phosphate; C43H37ClFeNiP2*C4H8O In 1,4-dioxane at 70℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; | 97% |
4-acetylphenylboronic acid
3-Bromo-4-methylpyridin
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 120℃; for 10h; Suzuki Coupling; | 97% |
Conditions | Yield |
---|---|
Stage #1: 3-Bromo-4-methylpyridin With lithium hexamethyldisilazane In tetrahydrofuran; ethylbenzene at 20℃; for 3h; Stage #2: carbonic acid dimethyl ester In tetrahydrofuran; ethylbenzene at 0 - 20℃; Stage #3: methyl iodide In tetrahydrofuran; ethylbenzene at -70 - 20℃; | 97% |
carbonic acid dimethyl ester
3-Bromo-4-methylpyridin
methyl 2-(3-bromopyridin-4-yl)acetate
Conditions | Yield |
---|---|
Stage #1: 3-Bromo-4-methylpyridin With lithium hexamethyldisilazane In tetrahydrofuran for 1.5h; Stage #2: carbonic acid dimethyl ester In tetrahydrofuran for 15h; | 96% |
Stage #1: 3-Bromo-4-methylpyridin With lithium hexamethyldisilazane In tetrahydrofuran; ethylbenzene at 20℃; for 3h; Stage #2: carbonic acid dimethyl ester In tetrahydrofuran; ethylbenzene at 0 - 20℃; | 95% |
With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; for 2.5h; | 85% |
With n-butyllithium; diisopropylamine 1.) THF, hexane, r.t. to 50 deg C, 2.) THF, hexane, 50 deg C; r.t., 24 h; Yield given. Multistep reaction; |
2-formylbenzene boronic acid
3-Bromo-4-methylpyridin
2-(4-methyl-pyridin-3-yl)-benzaldehyde
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; water; toluene at 90℃; for 15h; Inert atmosphere; | 96% |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; water; toluene at 90℃; for 15h; Suzuki coupling; | 94% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 70℃; for 12h; Suzuki Coupling; | 85% |
Conditions | Yield |
---|---|
With copper In water at 150 - 160℃; Temperature; Reagent/catalyst; | 95% |
With copper In water at 100 - 110℃; for 24h; Temperature; Autoclave; | 93% |
With copper(II) sulfate | 68% |
Conditions | Yield |
---|---|
Stage #1: 3-Bromo-4-methylpyridin With n-butyllithium In tetrahydrofuran at -100℃; for 0.166667h; Stage #2: Methyl formate In tetrahydrofuran at -96 - -78℃; for 1h; | 95% |
3-[4-methoxymethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine
3-Bromo-4-methylpyridin
3-[4-methoxymethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-5-(4-methyl-pyridin-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; | 95% |
N-boc-2-pyrroleboronic acid
3-Bromo-4-methylpyridin
tert-butyl 2-(4-methylpyridin-3-yl)-1H-pyrrole-1-carboxylate
Conditions | Yield |
---|---|
With potassium phosphate; C43H37ClFeNiP2*C4H8O In 1,4-dioxane at 70℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With ammonia; copper(II) sulfate In methanol at 160℃; under 3800.26 Torr; for 8h; Temperature; Autoclave; | 95% |
With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate In 1-methyl-pyrrolidin-2-one at 110℃; for 30h; | 80% |
3-Bromo-4-methylpyridin
3-iodo-4-methyl-pyridine
Conditions | Yield |
---|---|
With copper(l) iodide; N,N-dimethylethylenediamine; sodium iodide In 1,4-dioxane at 110℃; for 72h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 135℃; for 5h; | 95% |
3-bromo-1-(trimethylsilyl)-1-propyne
3-Bromo-4-methylpyridin
3-bromo-4-[4-(trimethylsilyl)but-3-yn-1-yl]pyridine
Conditions | Yield |
---|---|
Stage #1: 3-Bromo-4-methylpyridin With lithium diisopropyl amide In tetrahydrofuran; hexane at 50℃; for 0.75h; Stage #2: 3-bromo-1-(trimethylsilyl)-1-propyne In tetrahydrofuran; hexane at 0 - 20℃; Further stages.; | 93% |
sodium carbonate
3-Bromo-4-methylpyridin
formic acid ethyl ester
4-methylnicotinaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane; water | 93% |
3-Bromo-4-methylpyridin
3-bromo-4-methyl-1-oxidopyridin-1-ium
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 20℃; | 93% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h; |
3-Bromo-4-methylpyridin
formic acid ethyl ester
4-methylnicotinaldehyde
Conditions | Yield |
---|---|
Stage #1: 3-Bromo-4-methylpyridin With n-butyllithium In tetrahydrofuran; hexane at -100 - 100℃; for 0.166667h; Stage #2: formic acid ethyl ester In tetrahydrofuran; hexane at 100℃; for 0.5h; | 93% |
allyl bromide
3-Bromo-4-methylpyridin
3-bromo-4-(but-3-en-1-yl)pyridine
Conditions | Yield |
---|---|
Stage #1: 3-Bromo-4-methylpyridin With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.833333h; Stage #2: allyl bromide In tetrahydrofuran at -78 - 20℃; | 92% |
phenylacetylene
3-Bromo-4-methylpyridin
3-(phenylethynyl)-4-methylpyridine
Conditions | Yield |
---|---|
Stage #1: 3-Bromo-4-methylpyridin With bis(η3-allyl-μ-chloropalladium(II)); 1-n-butyl-3-methylimidazolium tetrafluoroborate; triphenylphosphine at 60℃; Heck alkynylation; Inert atmosphere; Stage #2: phenylacetylene With pyrrolidine at 100℃; for 4h; Heck alkynylation; Inert atmosphere; | 92% |
With tetrabutylammomium bromide; sodium acetate In dimethyl sulfoxide at 120℃; for 50h; Sonogashira Cross-Coupling; Inert atmosphere; | 69% |
benzofuran-2-boronic acid
3-Bromo-4-methylpyridin
3-(benzofuran-2-yl)-4-methylpyridine
Conditions | Yield |
---|---|
With C43H37ClFeNiP2*C4H8O; potassium carbonate In tetrahydrofuran; acetonitrile at 50℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; | 92% |
tributyl(1-ethoxyvinyl)stannane
3-Bromo-4-methylpyridin
3-(1-Ethoxy-vinyl)-4-methyl-pyridine
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In toluene for 4h; Heating / reflux; | 91% |
benzophenone hydrazone
3-Bromo-4-methylpyridin
diphenylmethanone (4-methylpyridin-3-yl)hydrazone
Conditions | Yield |
---|---|
With sodium t-butanolate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 85℃; | 91% |
Conditions | Yield |
---|---|
With sodium hydroxide; sodium tetrahydroborate In methanol stirring CoCl2, glyoxime in CH3OH at -20°C under N2; addn. of 50% aq. NaOH soln., 3-bromo-4-methylpyridine, NaBH4 in CH3OH; stirring at 20°C for 1 h; addn. of bromide at -20, stirring at 20°C in dark for 14 h;; addn. of water containing 1 drop 3-bromo-4-methylpyridine to oily residue; pptn.; drying; elem. anal.; | 91% |
(9-fluoro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinolin-7-yl)boronic acid
3-Bromo-4-methylpyridin
9-fluoro-1-methyl-7-(4-methyl-pyridin-3-yl)-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; palladium diacetate; sodium carbonate In ethanol; water; toluene Suzuki Coupling; Inert atmosphere; Reflux; | 91% |
3-Bromo-4-methylpyridin
3-bromoisonicotinic acid
Conditions | Yield |
---|---|
Stage #1: 3-Bromo-4-methylpyridin With Co0.27CuO3; water Stage #2: With oxygen at 90℃; | 90% |
With potassium permanganate In water Heating / reflux; | 32% |
With hydrogenchloride; potassium permanganate In water |
(5-(((tert-butoxycarbonyl)amino)methyl)furan-2-yl)boronic acid
3-Bromo-4-methylpyridin
Conditions | Yield |
---|---|
With trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 140℃; for 0.0333333h; Suzuki Coupling; Inert atmosphere; Microwave irradiation; | 89.4% |
With trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 140℃; for 0.0333333h; Microwave irradiation; Inert atmosphere; | 89% |
The 3-Bromo-4-methylpyridine is an organic compound with the formula C6H6BrN. The IUPAC name of this chemical is 3-bromo-4-methylpyridine. With the CAS registry number 3430-22-6, it is also named as 4-Bromobenzenamine. The product's categories are Blocks; Bromides; Pyridines; Pyridine; Pyridines, Pyrimidines, Purines and Pteredines; Halides; Pyridines Derivates; Aromatics Compounds; Bromopyridines; Halopyridines; Aromatics; C6Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Brominated Heterocyclic Series. Besides, it is a clear liquid, which should be stored in a dark dry and well-ventilated place.
Physical properties about 3-Bromo-4-methylpyridine are: (1)ACD/LogP: 2.05; (2)ACD/LogD (pH 5.5): 2.04; (3)ACD/LogD (pH 7.4): 2.05; (4)ACD/BCF (pH 5.5): 20.76; (5)ACD/BCF (pH 7.4): 21.27; (6)ACD/KOC (pH 5.5): 303.01; (7)ACD/KOC (pH 7.4): 310.5; (8)#H bond acceptors: 1; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 3.24 Å2; (12)Index of Refraction: 1.625; (13)Molar Refractivity: 38.17 cm3; (14)Molar Volume: 107.8 cm3; (15)Polarizability: 15.13×10-24cm3; (16)Surface Tension: 47.7 dyne/cm; (17)Density: 1.594 g/cm3; (18)Flash Point: 90.4 °C; (19)Enthalpy of Vaporization: 46.24 kJ/mol; (20)Boiling Point: 225.9 °C at 760 mmHg; (21)Vapour Pressure: 0.0843 mmHg at 25°C.
Uses of 3-Bromo-4-methylpyridine: it can be used to produce 4-methyl-nicotinonitrile by heating. It will need reagent dimethylformamide with reaction time of 8 hours. The yield is about 80%.
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 protective clothing.
You can still convert the following datas into molecular structure:
(1)SMILES: Brc1ccc(N)cc1
(2)InChI: InChI=1/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
(3)InChIKey: WDFQBORIUYODSI-UHFFFAOYAG
(4)Std. InChI: InChI=1S/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
(5)Std. InChIKey: WDFQBORIUYODSI-UHFFFAOYSA-N
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