ChemicalBook--->CAS DataBase List--->4583-55-5

4583-55-5

4583-55-5 Structure

4583-55-5 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2933998090
Hazard InformationBack 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]

2-Butanone

78-93-3

P-BROMOPHENYL HYDRAZINE

589-21-9

5-Bromo-2,3-dimethylindole

4583-55-5

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
Spectrum DetailBack Directory
[Spectrum Detail]

5-Bromo-2,3-dimethylindole(4583-55-5)1HNMR
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