3-Chloro-2-iodopyridine
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3-Chloro-2-iodopyridine
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CAS No:
77332-89-9
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Formula:
C5H3ClIN
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Chemical Name:
3-Chloro-2-iodopyridine
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Synonyms:
3-chloro-2-iodopyridine;Pyridine, 3-chloro-2-iodo-;3-chloro-2-iodo-pyridine;chloro-iodopyridine;2-Iodo-3-chloropyridine;Pyridine,3-chloro-2-iodo-;SCHEMBL366358;CTK5E4280;KS-00000NJK;DTXSID00445770
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CAS No:
Safety Information
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, P501
H302
|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|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
3-Chloro-2-iodopyridine Use and Manufacturing
General procedure: A solution of 1a (1.70 g, 1.40 mL, 15.0 mmol) or 1b (2.37 g, 1.44 mL, 15.0 mmol) in dry diethyl ether (60 mL) was cooled to 0 C and boron trifluoride etherate (BF3Et2O) in diethyl ether (2.34 g, 2.07 mL, 16.5 mmol) was added to it.2-Bromo-3-chloropyridine (6.25 g, 0.033 mol) and sodium iodide (14.5 g, 0.10 mol) were dissolved in propionitrile (26 mL). Chloro(trimethyl)silane (4.1 mL, 32 mmol) was then added dropwise to the mixture. After the bubbling stopped, the reaction mixture was brought to reflux under nitrogen for two hours. The mixture was diluted in EtOAc (75 mL) and washed three times with water (50 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo to give title compound as pale yellow solid (6.69 g, 86percent):2-Bromo-3-chloropyridine (6.25 g, 0.033 mol) and sodium iodide (14.5 g, 0.10 mol) were dissolved in propionitrile (26 mL). Chloro(trimethyl)silane (4.1 mL, 32 mmol) was then added dropwise to the mixture. After the bubbling stopped, the reaction mixture was brought to reflux under nitrogen for two hours. The mixture was diluted in EtOAc (75 mL) and washed three times with water (50 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo to give title compound as pale yellow solid (6.69 g, 86%):1H NMR (400 MHz, d6-DMSO): delta 7.42-7.45 (q, 1H), 7.94-7.97 (m, 1H), 8.30-8.32 (m, 1H)LCMS Rt=1.38 minutes MS m/z 240 [MH]+(B) Synthesis of 3-chloro-2-trifluoromethylisonicotinic acid; (1) 3-Chloro-2-iodopyridine was obtained from 2, 3- dichloropyridine by the method described in Eur. J. Org. Chem., (2002), 4181.Palladium(II) bromide (12.1 mg, 0.045 mmol) was added toa pre-degassed solution of 8-methyl-2-(methylthio)-5-oxo- 5, 8-dihydropyrido[2, 3-d]pyrimidine-6-carboxylic acid (228mg, 0.907 mmol),
Computed Properties
Molecular Weight:239.44
XLogP3:2.2
Hydrogen Bond Acceptor Count:1
Exact Mass:238.89987
Monoisotopic Mass:238.89987
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:78.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
