2-Bromo-5-iodopyridine
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2-Bromo-5-iodopyridine
structure -
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CAS No:
73290-22-9
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Formula:
C5H3BrIN
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Chemical Name:
2-Bromo-5-iodopyridine
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Synonyms:
2-Bromo-5-iodopyridine;Pyridine, 2-bromo-5-iodo-;MFCD03095201;2-Bromo-5-iodopyridine, 97%;2-Bromo-5-iodo-pyridine;PubChem5969;5-iodo-2-bromo-pyridine;ACMC-1BB8D;KSC493Q0P;SCHEMBL502933
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CAS No:
Characteristics
12.9
2.5
White to off-white Powder
2.3±0.1 g/cm3
121-123 °C(lit.)
278.6ºC at 760 mmHg
122.3±21.8 °C
1.666
Safety Information
IRRITANT
NONH for all modes of transport
3
22-37/38-41
26-36/39
Xn,Xi
P261-P280-P305 + P351 + P338
H302-H315-H318-H335
|Danger|H302 (88.64%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 44 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Bromo-5-iodopyridine Use and Manufacturing
Bromine (3ml) was added dropwise to a solution of 2-amino-5-iodo-pyridine (5g, 20mmol) in 48percent hydrobromic acid in water (10ml). AIL ice bath was used to cool the system. Sodium nitrite (3.4 g in 5ml of water) was then added dropwise so that the temperature does not go above 15°C. After the addition was complete, sodium hydroxide (16g) in water (40ml) was added. Brown solid precipitated and was extracted with DCM (50ml). The DCM extract was washed with water, brine, dried over MgS04 and evaporated in vacuo to give 2-bromo-5-iodo-pyridine (4.4g, 78percent).To a solution of 5-iodopyridin-2-amine(0.7 g, 3.18 mmol) in HBr [(1.26 g, 15.6 mmol (48percent in water)] at 0 00 sodium nitrite (0.746 g, 10.82 mmol) in water was added drop wise, followed by addition of bromine (1 .71 g, 10.82 mmol). The reaction mixture was kept at room temperature for 1 h. The reaction mixture was quenched with NaOH solution and extracted with ethyl acetate, washed with water, and dried overanhydrous Na2SO4. The solvent was removed under vacuo. The crude product was purified by column chromatography to yield title compound (0.6 g, 65.23percent) as a white solid. LCMS: (M+H) = 284; 1H NMR: (DMSO-d6, 300MHz) 6 8.64-8.65 (d, 1 H), 8.09- 8.12 (dd, 1H), 7.50-7.53 (m, 1H).To a solution of 5-iodopyridin-2-amine (0.7 g, 3.18 mmol) in HBr [(1.26 g, 15.6 mmol(48percent in water)] at 000 sodium nitrite (0.746 g, 10.82 mmol) in water was added dropwise followed by addition of bromine (1 .71 g, 10.82 mmol). The reaction mixture was at room temperature for 1 h. The reaction mixture was quenched with NaOH solution and extracted with ethyl acetate, washed with water, and dried over anhydrous Na2SO4 The solvent was removed under vacuo. The crude product was purified bycolumn chromatography to yield title compound (0.6 g, 65.23percent) as a white solid. LOMS: (M+H) = 284; 1H NMR: (DMSO-d6, 300MHz) 6 8.64-8.65 (d, 1H), 8.09-8.12 (dd, 1 H), 7.50-7.53 (m, 1 H).General procedure: (4-Nitrophenyl)boronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol, ), (CF
Computed Properties
Molecular Weight:283.89
XLogP3:2.5
Hydrogen Bond Acceptor Count:1
Exact Mass:282.84936
Monoisotopic Mass:282.84936
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:78.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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