4,6-Dichloro-2-pyridinamine
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4,6-Dichloro-2-pyridinamine
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CAS No:
116632-24-7
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Formula:
C5H4Cl2N2
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Chemical Name:
4,6-Dichloro-2-pyridinamine
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Synonyms:
2-Pyridinamine,4,6-dichloro-;Pyridine,2-amino-4,6-dichloro-;4,6-Dichloro-2-pyridinamine;2-Amino-4,6-dichloropyridine;4,6-Dichloropyridin-2-amine;(4,6-Dichloropyridin-2-yl)amine
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CAS No:
Characteristics
38.9
1.4
white crystalline powder
1.497±0.06 g/cm3(Predicted)
112.5 °C
287.9±35.0 °C(Predicted)
127.9±25.9 °C
1.623
0.00242mmHg at 25°C
Safety Information
22-36
26
Xn
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|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4,6-Dichloro-2-pyridinamine Use and Manufacturing
The dichloropyridine (652 mg, 4.0 mmol, 1.0 equiv) and the boronic acid (588 mg, 4.0 mmol, 1.0 equiv) were dissolved in CH3CN (16 mL, 0.25 M) in a 40 mL vial equipped with a magnetic stir bar. An aqueous solution of K2C03 (2 M, 2 mL, 4.0 mmol, 1.0 equiv) wasadded and the resulting solution was degassed by bubbling N2 for 10 minutes. Pd(PPh3)4 (231 mg, 0.2 mmol, 5 mol%) was then added and the mixture was heated to 80 C for 20 hours under a nitrogen atmosphere. Upon completion, the reaction mixture was diluted with EtOAc (20 mL), filtered over Celite, and concentrated in vacuo. The crude residue was purified by flash column chromatography over silica (hexanes/EtOAc gradient 0% to 100%) to afford the product as awhite solid (211 mg, 23% yield).The dichloropyridine (652 mg, 4.0 mmol, 1.0 equiv), PdC12(PPh3)2 (140 mg, 0.2 mmol, 5 mol%), and CuT (76 mg, 0.4 mmol, 10 mol%) were combined in Et3N/DMF (1:1, 16 mL, 0.25 M) in a 40 mL vial equipped with a magnetic stir bar. The resulting mixture was degassed by bubbling N2 for 10 minutes. Then, TMSA (2.2 mL, 16 mmol, 4.0 equiv) was added via syringe and the resulting mixture was stirred at 80 C for 3 h. Upon completion, the reactionmixture was cooled to room temperature and concentrated in vacuo. The resulting mixture was re-dissolved in EtOAc (30 mL) and filtered over Celite. The mixture was again concentrated in vacuo and the resulting residue was purified by flash column chromatography over silica (hexanes/EtOAc, gradient 0% to 100%) to afford the TMS-protected alkyne (692 mg, 77% yield).
Computed Properties
Molecular Weight:163.00
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:161.9751535
Monoisotopic Mass:161.9751535
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:99
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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