6-Bromo-1H-indole

6-Bromo-1H-indole Property

Melting point:

92-96 °C (lit.)

Boiling point:

70-75°C 0,01mm

Density 

1.660±0.06 g/cm3(Predicted)

Flash point:

70-75°C/0.01mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

16.07±0.30(Predicted)

form 

Powder

color 

White to brown

Sensitive 

Air & Light Sensitive

BRN 

112711

InChI

InChI=1S/C8H6BrN/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5,10H

InChIKey

MAWGHOPSCKCTPA-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(Br)=C2)C=C1

CAS DataBase Reference

52415-29-9(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

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.

6-Bromo-1H-indole Chemical Properties,Usage,Production

Chemical Properties

White to brown powder

Uses

Essential starter in 6-substituted indole chemistry.

Uses

6-Bromoindole is a starting material in the synthesis of various indole derivatives.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 249, 1984 DOI: 10.1021/jo00176a007

General Description

6-Bromoindole is an indole derivative. It undergoes palladium-catalyzed reaction with 2-(4-fluorophenyl)ethylpiperazine to afford the carbonylation products.

Synthesis

Step A: Under nitrogen protection, 4-bromo-2-nitrotoluene (7.9 g, 36.6 mmol) was dissolved in anhydrous N,N-dimethylformamide (73 mL), and N,N-dimethylformamide dimethyl acetal (14.5 mL, 110 mmol) and pyrrolidine (4.7 mL) were added sequentially. The reaction mixture was heated and stirred in an oil bath at 110 °C for 90 min. After completion of the reaction, the mixture was cooled to room temperature, diluted with ether (200 mL), and washed with deionized water (3 × 100 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was dissolved in 80% aqueous acetic acid (245 mL) and heated to 75 °C. Under stirring, zinc powder (20.8 g, 318 mmol) was added in batches for 2 hours. After addition, the reaction mixture was warmed to 85 °C and stirring was continued for 3.5 hours. After completion of the reaction, the mixture was cooled to room temperature and then to 0 °C in an ice bath and filtered to remove insoluble matter. The filtrate was diluted with ethyl acetate (200 mL) and washed with deionized water (2 × 100 mL). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a brown oily crude product. The crude product was purified by fast column chromatography with the eluent being a mixed solvent of hexane/ethyl acetate in the order of 95:5 and 90:10 to give 6-bromoindole as a gray solid (2.61 g, 36% yield). The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3): δ 8.14 (br s, 1H), 7.53 (s, 1H), 7.49 (d, J = 8.4 Hz, 1H), 7.21 (dd, J = 8.4, 1.7 Hz, 1H), 7.17-7.15 (m, 1H), 6.53-6.51 (m, 1H).

References

[1] Journal of Organic Chemistry, 2004, vol. 69, # 20, p. 6812 - 6820
[2] RSC Advances, 2014, vol. 4, # 9, p. 4672 - 4675
[3] Patent: US2006/52378, 2006, A1. Location in patent: Page/Page column 154
[4] Tetrahedron, 1999, vol. 55, # 4, p. 935 - 942
[5] Patent: US2011/46370, 2011, A1. Location in patent: Page/Page column 10