| Identification | More | [Name]
4-Bromo-1-chloroisoquinoline | [CAS]
66728-98-1 | [Synonyms]
4-BROMO-1-CHLOROISOQUINOLINE
1-Chloro-4-bromoisoquinoline | [EINECS(EC#)]
676-392-8 | [Molecular Formula]
C9H5BrClN | [MDL Number]
MFCD00234469 | [Molecular Weight]
242.5 | [MOL File]
66728-98-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
97 °C (decomp) | [Boiling point ]
328.8±22.0 °C(Predicted) | [density ]
1.673±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
-0.02±0.31(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C9H5BrClN/c10-8-5-12-9(11)7-4-2-1-3-6(7)8/h1-5H | [InChIKey]
HRWILRGBDZGABZ-UHFFFAOYSA-N | [SMILES]
C1(Cl)C2=C(C=CC=C2)C(Br)=CN=1 | [CAS DataBase Reference]
66728-98-1(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
4-Bromo-1-chloroisoquinoline is an isoquinoline derivative whose molecular structure contains substituents chlorine and bromine atoms at positions 1 and 4. The product can be used in metal-catalysed cross-coupling reactions and in the preparation of pharmaceuticals. | [Synthesis]
The general procedure for the synthesis of 4-bromo-1-chloroisoquinolines from 4-bromo-1(2H)-isoquinolinones was as follows: 4-bromoisoquinolin-1-ol (1.4 g, 5.80 mmol) was mixed with phosphorus trichloride (POCl3, 8.9 g, 58.09 mmol, 10 equiv.) and heated to reflux under stirring conditions. The progress of the reaction was monitored by liquid chromatography-mass spectrometry (LCMS) and it was confirmed that the reaction was completed after 4 hours. The reaction mixture was cooled to room temperature and the reaction was quenched with ice water (100 mL) followed by extraction with ethyl acetate (EtOAc, 3 x 25 mL). The organic phases were combined and washed sequentially with water (3 × 20 mL), saturated aqueous sodium bicarbonate (30 mL) and brine (20 mL). The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent to afford 4-bromo-1-chloroisoquinoline as a white solid 1.3 g in 87% yield. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222 |
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