6-Bromo-1H-indole Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

6-Bromo-1H-indole Usage And Synthesis

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

6-Bromo-1H-indole(52415-29-9)Related Product Information

• Ethyl 6-bromoindole-2-carboxylate
• 1H-Indole-3-aceticacid,6-bromo-(9CI)
• 6-Bromoindole-3-acetonitrile
• 6-BROMO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE
• 6-Bromoisoquinoline
• Arbidol hydrochloride
• Ethyl 6-bromo-5-hydroxy-1-methyl-2-(phenylsulfanylmethyl)indole-3-carboxylate
• 6-Bromo-1H-indole
• Brovincamine
• 7-Bromoindole-2-carboxylic acid
• 3-BROMO-1H-INDOLE
• 5-Bromoindole-3-carboxaldehyde
• Ethyl 4-bromo-1H-indole-2-carboxylate
• TERT-BUTYL 6-BROMO-1H-INDOLE-1-CARBOXYLATE
• 7-BROMO-1H-INDOLE-2-BORONIC ACID PINACOL ESTER
• Ethyl 3-bromoindole-2-carboxylate
• 7-AMINO-5-BROMOINDOLE
• 4-Bromoindole