2-Bromo-5-methyl-3-pyridinamine
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2-Bromo-5-methyl-3-pyridinamine
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CAS No:
34552-14-2
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Formula:
C6H7BrN2
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Chemical Name:
2-Bromo-5-methyl-3-pyridinamine
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Synonyms:
3-Pyridinamine,2-bromo-5-methyl-;2-Bromo-5-methyl-3-pyridinamine;3-Amino-2-bromo-5-methylpyridine;(2-Bromo-5-methylpyridin-3-yl)amine;2-Bromo-5-methylpyridin-3-amine;3-Amino-2-bromo-5-picoline
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CAS No:
Characteristics
38.9
1.6
1.593±0.06 g/cm3
106-107 °C
310°C at 760 mmHg
141.3±26.5 °C
1.617
H2O: Slightly soluble (6.4 g/L) (25 ºC)
Safety Information
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 5 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Bromo-5-methyl-3-pyridinamine Use and Manufacturing
1 -((3 S, 4R)-4-(3 , 4-difluorophenyl)- 1 -(2-methoxyethyl)pyrrolidin-3-yl)-3 -(5-methyl-2-phenylpyridin-3 -yl)urea1006131 Step A: Preparation of 2-bromo-5-methylpyridin-3-amine: Acetic acid (5 mL) was added dropwise to iron powder (1.11 g, 19.8 mmol) and the mixture was warmed to 80 °C. A solution of 2-bromo-5-methyl-3-nitropyridine (1.0 g, 4.61 mmol) in AcOH (5 mL) was then added dropwise over 20 minutes and the mixture stirred for a further 30 minutes. The mixture was stirred at ambient temperature for 16 hours then diluted with EtOAc (20 mL) and filtered through Celite®. The Celite® pad was washed well with EtOAc and the filtrate concentrated under vacuum. The residue was slowly treated with saturated NaHCO3 solution (50 mL) followed by portions of solid NaHCO3 until all the AcOH was neutralized. The mixture was then extracted with EtOAc (3 x 30 mE) and the combined organic phases were washed with brine (20 mE), dried over Na2SO4, filtered and concentrated to afford 2-bromo-5-methylpyridin-3-amine (799 mg, 93percent yield) as a bright yellow crystalline solid which darkened to a green color after drying under vacuum. MS (apci) mlz = 188.9 (M+H).Example 172: 2-Bromo-5-methyl-pyridin-3-ylamine; [00579] To Fe power (2.18 g, 39.0 mmol), AcOH (10 mL) was added drop wise and heated to 80 °C. To it, a solution of 2-bromo-5-methyl-3-nitro-pyridine (1.96 g, 9.07 mmol) in AcOH (10 mL) was added slowly. After 30 min, reaction mixture was allowed to cool to room temperature and diluted with EtOAc (25 mL), filtered through a pad of celite. The filter cake was washed with EtOAc (25 mL) and filterate was concentrated. The residual liquid was slowly treated with saturated aqueous NaHCO
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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