5-Bromo-1-methyl-1H-indole Chemical Properties

Melting point:

43 °C

Boiling point:

300.9±15.0 °C(Predicted)

Density 

1.47±0.1 g/cm3(Predicted)

Flash point:

>110℃

storage temp. 

Sealed in dry,Room Temperature

form 

solid

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C9H8BrN/c1-11-5-4-7-6-8(10)2-3-9(7)11/h2-6H,1H3

InChIKey

SBOITLSQLQGSLO-UHFFFAOYSA-N

SMILES

N1(C)C2=C(C=C(Br)C=C2)C=C1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38-41-37/38

Safety Statements 

22-26-36/37/39-39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933998090

5-Bromo-1-methyl-1H-indole Usage And Synthesis

Synthesis

1. 5-bromo-1H-indole (2.08 g, 10.6 mmol) was dissolved in 35 mL of DMF at 0 °C. 2. Sodium hydride (60% dispersed in mineral oil, 467 mg, 11.67 mmol) was added to the above solution, keeping the reaction temperature at 0 °C. 3. After stirring for 30 min, iodomethane (663 μL, 10.6 mmol) was slowly added. 4. The reaction mixture was gradually warmed to room temperature and stirring was continued for 10 min. 5. Upon completion of the reaction, the reaction was quenched with ice water at 0 °C. The reaction was then quenched with ice water. 6. The reaction mixture was extracted with ethyl acetate (3 × appropriate amount). 7. 7. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated. 8. The product was purified by fast column chromatography (eluent: 10% ethyl acetate/hexane) to give 5-bromo-1-methyl-1H-indole (2.16 g, 97% yield). 9. The product was analyzed by 1H NMR. 9. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.74 (d, J = 1.6 Hz, 1H), 7.30 (dd, J = 8.4, 2.0 Hz, 1H), 7.19 (d, J = 8.8 Hz, 1H), 7.05 (d, J = 3.2 Hz, 1H), 6.42 (d, J = 2.8 Hz, 1H), 3.78 (s, 3H), 6.42 (d, J = 2.8 Hz, 1H) 3.78 (s, 3H).

References

[1] Chemistry Letters, 1991, # 7, p. 1125 - 1128
[2] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 3, p. 333 - 336
[3] Organic Letters, 2015, vol. 17, # 2, p. 254 - 257
[4] Patent: WO2016/114816, 2016, A1. Location in patent: Paragraph 0332
[5] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 12, p. 4524 - 4529

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