| Identification | Back Directory | [Name]
TERT-BUTYL 5-BROMOINDOLE-1-CARBOXYLATE | [CAS]
182344-70-3 | [Synonyms]
N-Boc-5-bromoindole
1-BOC-5-bromoindole
1-Boc-5-bromo-1H-indole
N-Boc-5-bromoindole 13C6
5-Bromo-1-tert-butoxycarbonylindole
5-Bromo-1-(t-Butoxycarbonyl)-1H-indole
TERT-BUTYL 5-BROMOINDOLE-1-CARBOXYLATE
5-BROMO-1-(TERT-BUTOXYCARBONYL)-1H-INDOLE
TERT-BUTYL 5-BROMO-1H-INDOLE-1-CARBOXYLATE
5-bromo-1-indolecarboxylic acid tert-butyl ester
1H-Indole-1-carboxylic acid, 5-bromo-, 1,1-dimethylethyl ester | [Molecular Formula]
C13H14BrNO2 | [MDL Number]
MFCD02090067 | [MOL File]
182344-70-3.mol | [Molecular Weight]
296.16 |
| Chemical Properties | Back Directory | [Melting point ]
56-57 °C(lit.) | [Boiling point ]
367.9±34.0 °C(Predicted) | [density ]
1.37±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Solid | [color ]
White to off-white | [InChI]
InChI=1S/C13H14BrNO2/c1-13(2,3)17-12(16)15-7-6-9-8-10(14)4-5-11(9)15/h4-8H,1-3H3 | [InChIKey]
PBWDRTGTQIXVBR-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)C2=C(C=C(Br)C=C2)C=C1 |
| Hazard Information | Back Directory | [Uses]
N-Boc-5-bromoindole is formed as an intermediate for the synthesis of di-Boc-protected 5-aminoindole via a Buchwald-Hartwig amination with tBu-carbamate followed by regioselective bromination[1]. | [General Description]
N-Boc-5-bromoindole can undergo Sonogashira coupling reaction with N,N-diisopropylprop-2-ynylamine to afford the corresponding propargylic diisopropylamine. N-Boc-5-bromoindole is formed as an intermediate during the synthesis of 2-(5-substituted-1H-indol-3-yl)-N-hydroxyacetamide derivatives. | [Synthesis]
5-Bromoindole (5.0 g, 25.5 mmol), di-tert-butyl dicarbonate (7.6 mL, 33.1 mmol) and 4-dimethylaminopyridine (0.15 g, 1.23 mmol) were dissolved in acetonitrile (50 mL) and the reaction was stirred for 3 h at room temperature. After completion of the reaction, aqueous citric acid was added to the reaction mixture and extracted with ethyl acetate. The organic phase was washed with aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give N-tert-butoxycarbonyl-5-bromoindole (7.8 g, 100% yield) as a light yellow oil. | [References]
[1] Christoffer Bengtsson, et al. Rapid Construction of a Chloromethyl-Substituted Duocarmycin-like Prodrug. Molecules. 2023 Jun 16;28(12):4818. DOI:10.3390/molecules28124818 |
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