3,5-Dichloro-2-cyanopyridine
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3,5-Dichloro-2-cyanopyridine
structure -
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CAS No:
85331-33-5
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Formula:
C6H2Cl2N2
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Chemical Name:
3,5-Dichloro-2-cyanopyridine
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Synonyms:
2-PYRIDINECARBONITRILE, 3,5-DICHLORO-;2-CYANO-3,5-DICHLOROPYRIDINE;3,5-DICHLORO-2-CYANOPYRIDINE;3,5-Dichloropicolinitrile;3,5-Dichloropyridine-2-carbonitrile;3,5-dichloropicolinonitrile;Cyanodichloropyridine 235---;2-Cyano-3,5-dichloropyridine, 3,5-Dichloropicolinonitrile
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CAS No:
Characteristics
36.7
2.2
yellow powder
1.5±0.1 g/cm3
101-103°C
271.9ºC at 760 mmHg
118.2±25.9 °C
1.587
Room temperature.
Safety Information
III
6.1
3439
3
20/21/22-36/37/38
26-36/37/39-36-36/37
Xi,Xn
P261-P280-P305 + P351 + P338
H302-H312-H315-H319-H332-H335
|Warning|H302 (95.74%): 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 47 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3,5-Dichloro-2-cyanopyridine Use and Manufacturing
21.8 ml (0.174 mmol) of trimethylsilyl cyanide and 14.6 ml (0.158 mmol) of dimethylcarbamoyl chloride are added successively to a solution of 26 g (0.158 mol) of 3, 5-dichloropyridine 1-oxide (Johnson et al., J. Chem. Soc. B, 1967, 1211) in 80 ml of dichloromethane and stirred at room temperature for 48 hours. 100 ml of a 10percent strength aqueous NaHCO3 solution are added, and the mixture is vigorously stirred for 10 minutes. Separation of the phases is followed by extraction once with dichloromethane; the combined organic phases are dried and concentrated. The residue is chromatographed on silica gel with dichloromethane and recrystallized from a little methanol. [0167] 11 g (40.2percent) of 2-cyano-3, 5-dichloropyridine (melting point: 102° C.) are obtained.[0169] In analogy to Troschuetz, R. et al., J. Heterocycl. Chem. 33, 1815-1821 (1996), 150 ml of diethylene glycol dimethyl ether, 47.68 g (0.261 mol) of 2, 3, 5-trichloro-pyridine, 2.0 g (0.005 mol) of tetraphenylphosphonium bromide, 4.0 g (0.024 mol) of finely powdered potassium iodide and 75.0 g (0.838 mol) of copper(I) cyanide are mixed under nitrogen and stirred under reflux for 24 hours. Then a further 100 ml of diethylene glycol dimethyl ether, 2.0 g (0.005 mol) of tetraphenylphosphonium bromide, 4.0 g (0.024 mol) of finely powdered potassium iodide and 75 g (0.838 mol) of copper(I) cyanide are added, and the mixture is stirred at reflux temperature for a further 89 hours. Cooling to room temperature is followed by filtration with suction, and the filtrate is distilled to remove most of the diethylene glycol dimethyl ether. The residue is taken up in toluene and washed with an aqueous solution of Mohr's salt and then with aqueous NaHCO3 solution (peroxide test). It is then washed with water to remove diethylene glycol dimethyl ether. After filtration through cellit, the filtrate is dried over magnesium sulfate, and the solution is concentrated. [0170] 18.0 g (40.0percent) of 2-cyano-3, 5-dichloropyridine are obtained.
Computed Properties
Molecular Weight:173.00
XLogP3:2.2
Hydrogen Bond Acceptor Count:2
Exact Mass:171.9595035
Monoisotopic Mass:171.9595035
Topological Polar Surface Area:36.7
Heavy Atom Count:10
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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