4,4′-Dibromo-2,2′-bipyridine
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4,4′-Dibromo-2,2′-bipyridine
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CAS No:
18511-71-2
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Formula:
C10H6Br2N2
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Chemical Name:
4,4′-Dibromo-2,2′-bipyridine
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Synonyms:
2,2′-Bipyridine,4,4′-dibromo-;4,4′-Dibromo-2,2′-bipyridine;4,4′-Dibromo-2,2′-dipyridine;4,4′-Bromo-2,2′-bipyridine
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CAS No:
4,4′-Dibromo-2,2′-bipyridine Basic Attributes
313.97604
313.98
1806241-263-5
DTXSID30574527
29333990
Characteristics
25.8
2.9
1.809±0.06 g/cm3(Predicted)
141-142 °C @ Solvent: Ligroine
362.9±37.0 °C(Predicted)
173.3±26.5 °C
1.639
0mmHg at 25°C
Safety Information
36/37/38
26-36/37/39
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
4,4′-Dibromo-2,2′-bipyridine Use and Manufacturing
A 2 L round-bottom flask was substituted with nitrogen gas, and 37 g of Formula 4-c (0.1 mol) was added thereto, and dissolved by addition of 950 mL of chloroform. At -3° C., 297 g of tribromophosphine (1.1 mol) was slowly dropwise added thereto, followed by stirring at 60° C., for 2 hours. The resultant product was cooled to room temperature, added to 1 L of water, added with caustic soda until pH reached 11, and extracted with methylene chloride. Then, an organic layer was separated. After removal of moisture, and removal of a solvent by vacuum distillation, the precipitated solid was washed with ethanol, and filtered so as to provide a pale yellow solid, 26 g of Formula 4-d (yield 77percent).Phosphorous tribromide (6.0 mL, 54.0 mmol) was added dropwise to 2 (3.0 g, 16 mmol) in DMF (90.0 mL) at ambient temperature. The precipitation forms after the addition of PBr6 was synthesized according to a modified literature procedure.20 0.9 g (3.2 mmol) of a mixture consisting of 5 and 5awere suspended in 20 cm3 glacial acetic acid in a microwavevessel and 3 cm3 (40.5 mmol) acetyl bromidewere added. Themixture turned yellow immediately and themicrowave vesselwas sealed before it was heated to 130° C within ten minutesand a maximum power of 1000 MW. The reaction temperaturethen was maintained for 2 h after which the vessel wasallowed to cool to room temperature. The reaction mixturewas basified with a concentrated K2CO3 solution so that abrownish precipitate formed. The precipitate was collected, washed withwater and dried. For purification, the crude productwas dissolved in dichloromethane and filtered. After thesolvent was evaporated product was further purified by distillationunder reduced pressure to obtain as white solid. Singlecrystals of (6) were obtained by dissolving a sample of thecompound in the minimum amount of ethanol, adding wateruntil a low haze was observed and storing the solution in arefrigerator (4° C) overnight.Yield: 81percent (0.825 g, 2.6 mmol);melting point: 141–142° C, literature: 135–136° C.21
Computed Properties
Molecular Weight:313.98
XLogP3:2.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:313.88772
Monoisotopic Mass:311.88977
Topological Polar Surface Area:25.8
Heavy Atom Count:14
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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