| Identification | Back Directory | [Name]
5-Bromo-2,3-dimethylindole | [CAS]
4583-55-5 | [Synonyms]
5-Bromo-2,3-dimethylindole
5-broMo-2,3-diMethyl-1H-indole
1H-Indole, 5-bromo-2,3-dimethyl- | [Molecular Formula]
C10H10BrN | [MDL Number]
MFCD00850844 | [MOL File]
4583-55-5.mol | [Molecular Weight]
224.11 |
| Chemical Properties | Back Directory | [Melting point ]
136-137℃ | [Boiling point ]
135-137 °C(Press: 10 Torr) | [density ]
1.487 | [refractive index ]
1.5923 | [storage temp. ]
2-8°C | [pka]
16.91±0.30(Predicted) | [Appearance]
Light yellow to orange Solid |
| Hazard Information | Back Directory | [Uses]
5-Bromo-2,3-dimethylindole is used to prepare 1-[(arylsulfonyl)amino]alkylindole derivatives as dual thromboxane synthase inhibitor/thromboxane receptor antagonists. It is also used to prepare modulators of secreted frizzled related protein-1 (SFRP-1). | [Synthesis]
Procedure for the synthesis of 5-bromo-2,3-dimethylindole: A mixture of 4-bromophenylhydrazine (5.0 g, 22.3 mmol) and 2-butanone (1.6 g, 22.3 mmol) was dissolved in ethanol (60 mL) and the reaction was heated overnight under reflux conditions. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was recrystallized from the ethanol/water solvent mixture to afford the target product 5-bromo-2,3-dimethylindole (3.6 g, 73% yield). The structure of the product was confirmed by NMR hydrogen spectrum (400 MHz, d6-DMSO): δ 10.87 (s, 1H), 7.51 (d, J = 1.2 Hz, 1H), 7.18 (d, J = 6.3 Hz, 1H), 7.07 (dd, J = 6.3 Hz, 1.2 Hz, 1H), 2.31 (s, 3H), 2.13 (s, 3H). | [References]
[1] Patent: WO2015/74123, 2015, A1. Location in patent: Page/Page column 47 |
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