2-Amino-5-bromo-3-methylpyridine
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2-Amino-5-bromo-3-methylpyridine
structure -
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CAS No:
3430-21-5
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Formula:
C6H7BrN2
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Chemical Name:
2-Amino-5-bromo-3-methylpyridine
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Synonyms:
2-Pyridinamine,5-bromo-3-methyl-;3-Picoline,2-amino-5-bromo-;5-Bromo-3-methyl-2-pyridinamine;2-Amino-5-bromo-3-methylpyridine;2-Amino-3-methyl-5-bromopyridine;5-Bromo-3-methylpyridin-2-ylamine;5-Bromo-3-methyl-2-aminopyridine;2-Amino-5-bromo-3-picoline
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CAS No:
Characteristics
38.9
1.6
off-white crystal
1.6±0.1 g/cm3
90-92 °C
250ºC at 760 mmHg
105.0±25.9 °C
1.617
Safety Information
IRRITANT
NONH for all modes of transport
3
36/37/38
26-36-36/37
Xi
Irritant
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 136 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Amino-5-bromo-3-methylpyridine Use and Manufacturing
Bromine (15.4 mL, 0.30 mol) was added dropwise to a stirred and cooled (0-2 [°C)] solution of 2-amino-3-picoline (1; 32.44 g, 0.30 mol) in dry [CH2CI2] (1000 mL) over a period of 1 h. The cooling bath was then removed, and the yellowish suspension was stirred at r. t. for 3 h 40 min. The mixture was basified to pH 9 with 2N [NAOH] (145 mL) followed by a mixture of saturated aqueous [NAHC03] (100 mL) -saturated aqueous Na2S203 (10 mL). The organic layer was separated and washed with brine, dried [MGS04] and concentrated to afford 14 (56.83 g, 102percent) as brown solid, which was used in the next step without purification.5-Bromo-3-methylpyridin-2-amine (48) [0174] (J. Mol. Catal. A: Chem. 2007, 267, 30-33.) N-Bromosuccinimide (170 g, 0.95 mol) was added to a solution of 47 (99 g, 0.92 mol) and ammonium acetate (7 g, 10 mol percent) in acetonitrile (500 mL). The temperature of the reaction mixture during addition was controlled with an ice bath. After the full amount of NBS was added, the ice bath was removed and the reaction mixture was stirred at room temperature for 25 min, and acetonitrile was removed under reduced pressure. A mixture of ethyl acetate (1 L) and water (1 L) was added to the solid residue. The resulting mixture was stirred and the organic layer was separated. The water layer was extracted with ethyl acetate (3×500 mL). The combined extracts were washed with water (300 mL), saturated sodium bicarbonate solution (500 L), dried with sodium sulfate and evaporated to dryness to give a dark brown solid. The crude product was redissolved in chloroform (300 mL); and the solution was filtered through a thin pad of silica gel, eluting with chloroform. The combined filtrates were evaporated under reduced pressure to yield 48 as a light-brown solid (113 g, 65percent): mp 89-90° C. (lit. (J. Am. Chem. Soc. 1976, 98, 1478-1486) mp 91-93° C.). General procedure: To a mixture of 2-aminopyridine (0.5 mmol, 1 equiv), p-TSA (0.4 mmol, 0.8 equiv), 1-butylpyridinium bromide (1.5 mmol, 3 equiv) in a 50 mL Schlenk tube were added 1, 2-dimethoxyethane (2 mL) under air. Then H
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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2-Amino-5-bromo-3-methylpyridine
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