| Identification | More | [Name]
3-Bromo-5-iodo-pyridine | [CAS]
233770-01-9 | [Synonyms]
3-BROMO-5-IODO-PYRIDINE
5-BROMO-3-IODOPYRIDINE | [Molecular Formula]
C5H3BrIN | [MDL Number]
MFCD03086019 | [Molecular Weight]
283.89 | [MOL File]
233770-01-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white Cryst | [Melting point ]
127-131 °C | [Boiling point ]
266.5±25.0 °C(Predicted) | [density ]
2.347±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
Solid | [pka]
0.85±0.20(Predicted) | [color ]
Off-white | [Water Solubility ]
Slightly soluble in water. | [Sensitive ]
Light Sensitive | [InChI]
InChI=1S/C5H3BrIN/c6-4-1-5(7)3-8-2-4/h1-3H | [InChIKey]
AOOZLVWDZUPEHT-UHFFFAOYSA-N | [SMILES]
C1=NC=C(I)C=C1Br | [CAS DataBase Reference]
233770-01-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H302-H318 | [Precautionary statements ]
P280-P301+P312+P330-P305+P351+P338+P310 | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes.
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3 | [Hazard Note ]
Harmful | [HazardClass ]
IRRITANT | [HS Code ]
2933399990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white Cryst | [Uses]
Reactant in the synthesis chiral 4, 4?-Bipyridines. 3-bromo-5-(trifluoromethyl)pyridine is prepared from 3-Bromo-5-iodopyridine. | [Synthesis]
General procedure for the synthesis of 3-bromo-5-iodopyridine from 3,5-dibromopyridine: 3,5-dibromopyridine (0.52 g, 2.19 mmol) was dissolved in anhydrous tetrahydrofuran (4 mL) at -10 °C, keeping the internal temperature below -5 °C. Subsequently, tetrahydrofuran solution of 2M isopropylmagnesium chloride (0.25 g, 2.11 mmol) and anhydrous tetrahydrofuran solution of iodine (0.62 g, 2.11 mmol) were added sequentially and slowly and stirred for about 5 minutes. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and saturated aqueous sodium bisulfite. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated to afford 3-bromo-5-iodopyridine (4.85 g, 98% yield), which can be used directly for further purification. The product characterization data were as follows: 1H NMR (400 MHz, CDCl3) δ 7.54-7.51 (m, 1H), 8.26 (s, 1H), 8.42 (s, 1H); MS (ES): m/z = 284 [M + H]+. | [References]
[1] Patent: WO2005/94822, 2005, A1. Location in patent: Page/Page column 35
[2] Chemistry - A European Journal, 2010, vol. 16, # 41, p. 12425 - 12433
[3] European Journal of Organic Chemistry, 2002, # 2, p. 327 - 330
[4] Patent: US2006/4018, 2006, A1. Location in patent: Page/Page column 12; 27
[5] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1062,1068 |
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