| Identification | Back Directory | [Name]
4-Iodo-2-(trifluoromethyl)pyridine | [CAS]
590371-73-6 | [Synonyms]
4-IODO-2-(TRIFLUOROMETHYL)PYRIDINE
2-(trifluoroMethyl)-4-iodopyridine
4-IODE-2-(TRIFLUOROMETHYL)PYRIDINE
Pyridine,4-iodo-2-(trifluoromethyl)-
4-Iodo-2-(trifluoromethyl)pyridine97%
4-Iodo-2-(trifluoromethyl)pyridine 97%
4-Iodo-2-(trifluoromethyl)pyridine ISO 9001：2015 REACH | [Molecular Formula]
C6H3F3IN | [MDL Number]
MFCD08234939 | [MOL File]
590371-73-6.mol | [Molecular Weight]
272.99 |
| Chemical Properties | Back Directory | [Melting point ]
24-26 °C | [Boiling point ]
206.2±35.0 °C(Predicted) | [density ]
1.974g/ml | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
liquid | [pka]
-0.82±0.20(Predicted) | [color ]
Clear, colourless to pale yellow | [InChI]
InChI=1S/C6H3F3IN/c7-6(8,9)5-3-4(10)1-2-11-5/h1-3H | [InChIKey]
OYQSAEIWDLIZHC-UHFFFAOYSA-N | [SMILES]
C1(C(F)(F)F)=NC=CC(I)=C1 |
| Hazard Information | Back Directory | [Uses]
4-Iodo-2-(trifluoromethyl)pyridine is used as a reagent in the synthesis of aminoisoindoles as β-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitors which exhibit in vivo brain reduction of β-amyloid peptides. | [Reactivity Profile]
4-Iodo-2-(trifluoromethyl)pyridine could be cleanly deprotonated by
LIDA in tetrahydrofuran at –75 °C[1]. Trapping of the organometallic intermediates with dry ice followed by neutralization gave the 4-iodo-2-(trifluoromethyl)pyridine-3-carboxylic acid (16, 31%). a: LIDA in THF at –75 °C for 2 h; b: (1.) Excess solid
carbon dioxide, (2.) Hydrochloric acid. | [Synthesis]
The general procedure for the synthesis of 4-iodo-2-(trifluoromethyl)pyridine from 3-iodo-2-trifluoromethylpyridine was as follows: a hexane solution (7.2 mL) of 2.5 M butyl lithium was diluted in tetrahydrofuran (30 mL) and cooled to -78 °C in a dry ice/acetone bath. Subsequently, diisopropylamine (2.5 mL) and 3-iodo-2-trifluoromethylpyridine (4.9 g) obtained in Step A were added dropwise to this cooled solution. The reaction mixture was stirred continuously at -78 °C for 2 h. The reaction was subsequently quenched with methanol (2 mL) at the same temperature. The reaction mixture was concentrated and purified by fast column chromatography (silica gel, cyclohexane/ethyl acetate as eluent) to afford 4-iodo-2-(trifluoromethyl)pyridine as yellow acicular crystals (1.6 g, 32% yield). The structure of the product was confirmed by 1H-NMR (CDCl3): δ = 8.40 (d, 1H), 8.06 (s, 1H), 7.90 (d, 1H). | [References]
[1] Schlosser M, et al. Further Metalations and Functionalizations of Chloro-, Bromo- and
Iodo(trifluoromethyl)pyridines. Synthesis, 2004; 10: 1619-1624. |
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