| Identification | Back Directory | [Name]
2-Bromo-5-trifluoromethoxypyridine | [CAS]
888327-36-4 | [Synonyms]
2-Bromo-5-(trifluoromethoxy)
2-Bromo-5-trifluoromethoxypyridine
Pyridine,2-bromo-5-(trifluoromethoxy)- | [Molecular Formula]
C6H3BrF3NO | [MDL Number]
MFCD10698596 | [MOL File]
888327-36-4.mol | [Molecular Weight]
242 |
| Chemical Properties | Back Directory | [Boiling point ]
63-66 °C(Press: 11 Torr) | [density ]
1.737±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
liquid | [pka]
-3.55±0.10(Predicted) | [color ]
Clear, almost colourless | [InChI]
InChI=1S/C6H3BrF3NO/c7-5-2-1-4(3-11-5)12-6(8,9)10/h1-3H | [InChIKey]
RKXYQQVLVNEAFB-UHFFFAOYSA-N | [SMILES]
C1(Br)=NC=C(OC(F)(F)F)C=C1 |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 2-bromo-5-trifluoromethoxypyridine: 2-chloro-5-(trifluoromethoxy)pyridine (6, 7.0 g, 35.4 mmol) and bromotrimethylsilane (10.8 g, 9.3 mL, 70.8 mmol, 2 eq.) were dissolved in propionitrile (35 mL) and heated to reflux for 24 hours. The reaction process was monitored by gas chromatography (GC) to confirm 100% conversion. Upon completion of the reaction, the mixture was vacuum distilled to afford pure 2-bromo-5-trifluoromethoxypyridine (31, 7.0 g, 28.7 mmol, 81% yield) as a colorless oil. Boiling point: 63-66°C (14 mbar).
NMR data:
1H NMR (CDCl3, 300 MHz): δ= 8.34 (d, J = 2.8 Hz, 1H), 7.56 (d, J = 8.7 Hz, 1H), 7.45 (dd, J = 8.7, 2.8 Hz, 1H).
19F NMR (CDCl3, 282 MHz): δ= -58.8.
13C NMR (CDCl3, 75 MHz): δ= 145.6, 143.1, 139.2, 131.4, 129.0, 120.1 (q, J = 260 Hz).
Elemental analysis: C6H3BrF3NO (molecular weight 241)
Calculated value (%): C 29.78, H 1.25, N 5.79; measured value: C 29.96, H 1.41, N 5.64. | [References]
[1] Patent: WO2010/40461, 2010, A1. Location in patent: Page/Page column 38-39
[2] European Journal of Organic Chemistry, 2010, # 31, p. 6043 - 6066 |
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