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CAS No.: | 3430-17-9 |
---|---|
Name: | 2-Bromo-3-methylpyridine |
Article Data: | 22 |
Molecular Structure: | |
Formula: | C6H6BrN |
Molecular Weight: | 172.024 |
Synonyms: | 2-bromo-3-methyl-pyridine;2-Bromo-3-picoline; |
EINECS: | -0 |
Density: | 1.494 g/cm3 |
Boiling Point: | 215.3 °C at 760 mmHg |
Flash Point: | 84 °C |
Appearance: | clear slightly yellow to light brown liquid |
Hazard Symbols: | Xn, Xi |
Risk Codes: | 36/37/38-20/21/22 |
Safety: | 26-37/39-36/37/39-36 |
PSA: | 12.89000 |
LogP: | 2.15250 |
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. |
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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