TERT-BUTYL 5-BROMOINDOLE-1-CARBOXYLATE

TERT-BUTYL 5-BROMOINDOLE-1-CARBOXYLATE Property

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

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

TERT-BUTYL 5-BROMOINDOLE-1-CARBOXYLATE Chemical Properties,Usage,Production

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