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3430-22-6

Basic Information
CAS No.: 3430-22-6
Name: 3-Bromo-4-methylpyridine
Article Data: 14
Molecular Structure:
Molecular Structure of 3430-22-6 (3-Bromo-4-methylpyridine)
Formula: C6H6BrN
Molecular Weight: 172.024
Synonyms: 3-Bromo-4-picoline;4-Methyl-3-Bromopyridine;
EINECS: 608-967-6
Density: 1.594 g/cm3
Boiling Point: 225.9 °C at 760 mmHg
Flash Point: 90.4 °C
Appearance: Clear Liquid
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 36/37/38-20/21/22
Safety: 26-36
PSA: 12.89000
LogP: 2.15250
Synthetic route
3430-27-1

3-amino-4-methylpyridine

3430-22-6

3-Bromo-4-methylpyridin

Conditions
ConditionsYield
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;
108-89-4

picoline

3430-22-6

3-Bromo-4-methylpyridin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
THF, -60 -> -55.deg C, 1) 15 min, 2) 45 min; Yield given. Multistep reaction. Yields of byproduct given;
626-55-1

3-Bromopyridine

74-88-4

methyl iodide

3430-22-6

3-Bromo-4-methylpyridin

Conditions
ConditionsYield
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
ConditionsYield
With o-tetrachloroquinone In acetic acid for 8h; Ambient temperature; Yield given;
626-55-1

3-Bromopyridine

3430-22-6

3-Bromo-4-methylpyridin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; water; toluene at 90℃; for 15h; Suzuki coupling;98%
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    Name: 3-Bromo-4-Methylpyridine Molecular Formula:C6H6BrN Molecular Weight:172.02 CAS No.:3430-22-6 Appearance:Colorless To Slight Yellow Liquid Appearance:Colorless To Slight Yellow Liquid Storage:Preserve in well-closed, light-resistant and airt

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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%.

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