| Identification | More | [Name]
5-Bromo-2-iodopyridine | [CAS]
223463-13-6 | [Synonyms]
2-IODO-5-BROMOPYRIDINE
5-BROMO-2-IODOPYRIDINE
PYRIDINE, 5-BROMO-2-IODO-
5-Bromo-2-Iodopyridine99%
5-BROMO-2-IDIOPYRIDINE
5-bromo-2-lodopyridine
5-BROMO-2-IODOPYRIDINE 97%
5-bromo-2-iodopyridine 97% 5g
5-Bromo-2-iodopyridine, 98+% | [EINECS(EC#)]
606-990-6 | [Molecular Formula]
C5H3BrIN | [MDL Number]
MFCD00691506 | [Molecular Weight]
283.89 | [MOL File]
223463-13-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow Cryst | [Melting point ]
113-117 °C (lit.) | [Boiling point ]
258.8±20.0 °C(Predicted) | [density ]
2.347±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO, Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
-0.51±0.10(Predicted) | [color ]
White to beige | [Sensitive ]
Light Sensitive | [BRN ]
2119 | [Stability:]
Light Sensitive | [InChI]
InChI=1S/C5H3BrIN/c6-4-1-2-5(7)8-3-4/h1-3H | [InChIKey]
HSNBRDZXJMPDGH-UHFFFAOYSA-N | [SMILES]
C1(I)=NC=C(Br)C=C1 | [CAS DataBase Reference]
223463-13-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT, LIGHT SENSITIVE | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow Cryst | [Uses]
5-Bromo-2-iodopyridine may be used in the synthesis of the following:
- 5-bromopyridyl-2-magnesium chloride via reaction with isopropylmagnesium chloride solution
- 5-bromo-2-pyridylzinc iodide via treatment with active zinc in tetrahydrofuran
- 5-bromo-2-(trifluoromethyl)pyridine via halogen/trifluoromethyl displacement reaction
- (5-bromopyridin-2-yl)zinc(II) chloride via multi-step synthesis
- 5,5′-dibromo-2,2′-bipyridine via multi-step synthesis
| [Synthesis]
The general procedure for the synthesis of 5-bromo-2-iodopyridine from 2,5-dibromopyridine was as follows: an aqueous solution of 57% hydriodic acid (HI) was added to a reaction system containing 2,5-dibromopyridine (12.60 g, 53.2 mmol) and sodium iodide (NaI, 11.40 g, 76 mmol). The reaction mixture was heated to reflux for 24 h, subsequently cooled to room temperature and diluted with 100 mL of water. The pH of the mixture was adjusted to alkaline with sodium bicarbonate (NaHCO3), and then treated with the addition of sodium dithionite (Na2S2O4) until the solution became colorless. The reaction mixture was extracted with dichloromethane (DCM, 5 x 60 mL), the organic phases were combined and dried over anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure and the obtained residue was collected by filtration, washed with ether (Et2O, 60 mL) and dried over air to give 5-bromo-2-iodopyridine (8.28 g, 55% yield) as a light gray powder. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4528 - 4532
[2] Chemical Communications, 2012, vol. 48, # 8, p. 1120 - 1122
[3] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
[4] Journal of Organic Chemistry, 2001, vol. 66, # 2, p. 605 - 608
[5] Organic Letters, 2004, vol. 6, # 26, p. 4905 - 4907 |
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