6-Azaindole Chemical Properties

Melting point:

136-137°C

Boiling point:

295.8±13.0 °C(Predicted)

Density 

1.242±0.06 g/cm3(Predicted)

RTECS 

UY8720000

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

Solid

pka

14.66±0.30(Predicted)

Appearance

Off-white to light brown Solid

Water Solubility 

Soluble in water (hardly), methanol and chloroform.

Sensitive 

Air & Light Sensitive

InChI

InChI=1S/C7H6N2/c1-3-8-5-7-6(1)2-4-9-7/h1-5,9H

InChIKey

XLKDJOPOOHHZAN-UHFFFAOYSA-N

SMILES

C1=NC=CC2C=CNC1=2

CAS DataBase Reference

271-29-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

29339980

Toxicity

mouse,LD50,intraperitoneal,12mg/kg (12mg/kg),Journal of Medicinal Chemistry. Vol. 6, Pg. 480, 1963.

6-Azaindole Usage And Synthesis

Chemical Properties

crystals

Uses

6-Azaindole is an indole derivative and useful synthetic intermediate.

Synthesis

General procedure for the synthesis of 6-azaindole using 7-chloro-1H-pyrrolo[2,3-c]pyridine as starting material: a suspension of 7-chloro-1H-pyrrolo[2,3-c]pyridine (650 mg, 4.2 mmol) with 10% Pd/C (50 mg) in ethanol (25 mL) was subjected to a hydrogen atmosphere (balloon pressure) and the reaction was stirred at room temperature. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filter cake was washed with ethyl acetate (10 mL). The filtrates were combined, concentrated under reduced pressure and subsequently purified by fast column chromatography (eluent: dichloromethane/methanol/ammonia, 9:1:0.1, v/v) to afford 1H-pyrrolo[2,3-c]pyridine as a white solid (380 mg, 75% yield).

References

[1] Journal of Organic Chemistry, 2002, vol. 67, # 7, p. 2345 - 2347
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9531 - 9540
[3] Patent: US2007/123535, 2007, A1. Location in patent: Page/Page column 43
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5086 - 5098
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4009 - 4022

6-Azaindole(271-29-4)Related Product Information

• Indometacin
• Indole-3-acetic acid
• Indoline
• Indole-3-butyric acid
• Pyridine
• 7-Azaindole
• 4-Azaindole
• 1H-Pyrrolo[3,2-c]pyridine, 5-Azaindole
• HARMANE
• BANISTERINE MONOHYDRATE
• N-METHYL-BETA-CARBOLINE-3-CARBOXAMIDE
• HARMAN HYDROCHLORIDE
• HARMOL HYDROCHLORIDE
• 9H-PYRIDO[3,4-B]INDOLE
• SEMPERVIRINE NITRATE
• SERPENTINE HYDROGEN TARTRATE
• HARMINE HYDROCHLORIDE
• 3-Iodo-7-azaindole