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Cas Database |
| Name |
3-Bromo-4-methylpyridine |
EINECS | 608-967-6 |
| CAS No. | 3430-22-6 | Density | 1.594 g/cm3 |
| PSA | 12.89000 | LogP | 2.15250 |
| Solubility | N/A | Melting Point |
N/A |
| Formula | C6H6BrN | Boiling Point | 225.9 °C at 760 mmHg |
| Molecular Weight | 172.024 | Flash Point | 90.4 °C |
| Transport Information | N/A | Appearance | Clear Liquid |
| Safety | 26-36 | Risk Codes | 36/37/38-20/21/22 |
| Molecular Structure |
|
Hazard Symbols |
 Xn,  Xi
|
| Synonyms |
3-Bromo-4-picoline;4-Methyl-3-Bromopyridine; |
Article Data | 14 |
3-Bromo-4-methylpyridine Synthetic route
| 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; |
- 626-55-1
3-Bromopyridine
- 4111-54-0
lithium diisopropyl amide
- 74-88-4
methyl iodide
A
- 1120-87-2
4-bromopyridin
B
- 10168-00-0
4-bromo-3-methylpyridine
C
- 3430-22-6
3-Bromo-4-methylpyridin
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at -60℃; Product distribution; Mechanism; temp. change; |
- 626-55-1
3-Bromopyridine
- 74-88-4
methyl iodide
A
- 10168-00-0
4-bromo-3-methylpyridine
B
- 3430-22-6
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; |
- 90731-85-4
3-Bromo-4-methyl-4H-pyridine-1-carboxylic acid phenyl ester
- 3430-22-6
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 |
- 3430-22-6
3-Bromo-4-methylpyridin
- 89641-18-9
2,4-dimethoxypyrimidin-5-ylboronic acid
- 952403-13-3
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% |
- 3430-22-6
3-Bromo-4-methylpyridin
- 105-58-8
Diethyl carbonate
- 51054-99-0
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% |
- 94838-88-7
2-formyl-4,5-(methylenedioxy)benzeneboronic acid
- 3430-22-6
3-Bromo-4-methylpyridin
- 1086561-33-2
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% |
3-Bromo-4-methylpyridine Specification
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%.
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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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