2-BROMO-5-AMINO-4-PICOLINE
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2-BROMO-5-AMINO-4-PICOLINE
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CAS No:
156118-16-0
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Formula:
C6H7BrN2
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Chemical Name:
2-BROMO-5-AMINO-4-PICOLINE
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Synonyms:
2-BROMO-5-AMINO-4-PICOLINE;5-Amino-2-bromo-4-methylpyridine;3-Amino-6-bromo-4-methylpyridine;3-Pyridinamine, 6-bromo-4-methyl-;6-Bromo-4-methyl-3-pyridinamine;6-BroMo-4-Methyl-pyridin-3-ylaMine;2-BROMO-5-AMINO-4-PICOLIN...
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CAS No:
Characteristics
38.9
1.6
Brown Powder
1.593±0.06 g/cm3(Predicted)
306.9±37.0 °C(Predicted)
139.4±26.5 °C
1.617
0.000752mmHg at 25°C
Safety Information
6.1
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
2-BROMO-5-AMINO-4-PICOLINE Use and Manufacturing
A suspension of 2-bromo-4-methyl-5-nitropyridine (XIV) (200 g, 921 mmol, 1.00 eq) and NH4C1 (240 g, 4.49 mol, 4.87 eq) in EtOH (3.50 L) and water (150 mL) was heated with stirring to 50°C. To this mixture was added Fe (120 g, 2.15 mol, 2.33 eq) and HC1 (10.2 g, 279 mmol, 0.30 eq). The suspension was then heated to 80°C for another 3 h. The reaction was cooled to 25°C and filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to yield a residue that was taken up in EtOAc (1 Lx 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6- bromo-4-methylpyridin-3-amine (XV) as brown solid (167.9 g, 898 mmol, 97.4percent yield) which was used for the next step without any purification. ‘H NMR (CDC13, 400 MHz) ppm 2.15 (s, 3H), 3.44 (br s, 2H), 7.14 (s, 1H), 7.78 (s, 1H); ESIMS found for C6H7BrN2 mlz 186.8 (M+H).A suspension of 2-bromo-4-methyl-5-nitropyridine (XIV) (200 g, 921 mmol, 1.00 eq) and NH4C1 (240 g, 4.49 mol, 4.87 eq) in EtOH (3.50 L) and water (150 mL) was heated with stirring to 50°C. To this mixture was added Fe (120 g, 2.15 mol, 2.33 eq) and HC1 (10.2 g, 279 mmol, 0.30 eq). The suspension was then heated to 80°C for another 3 h. The reaction was cooled to 25°C and filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to yield a residue that was taken up in EtOAc (1 Lx 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6- bromo-4-methylpyridin-3-amine (XV) as brown solid (167.9 g, 898 mmol, 97.4percent yield) which was used for the next step without any purification. ‘H NMR (CDC13, 400 MHz) ppm 2.15 (s, 3H), 3.44 (br s, 2H), 7.14 (s, 1H), 7.78 (s, 1H); ESIMS found for C6H7BrN2 mlz 186.8 (M+H).To a solutionof 2-bromo-4-methyl-5-nitropyridine (5.00 g, 23.0 mmol) in tetrahydrofuran (THF)(30 ml) was added Raney nickel (slurry in water). The reaction mixture washydrogenated (balloon) overnight at room temperature. The mixture was filteredthrough Celite, and concentrated under reduced pressure. The residue waspurified by silica gel column chromatography (0-50percent EtOAc in hexanes) to afford27 as a yellow solid (4.02 g, 93percentyield).
Computed Properties
Molecular Weight:187.04
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:185.97926
Monoisotopic Mass:185.97926
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:97.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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InquiryCAS No.: 156118-16-0Grade: Industrial GradeContent: 99%
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