| Identification | More | [Name]
6-Azaindole | [CAS]
271-29-4 | [Synonyms]
Harmyrine
1,6-Diazaindene
1H-PYRROLO[2,3-C]PYRIDINE 6-AZAINDOLE
1H-Pyrrolo[2,3-c]pyridine
6-Azaindole | [EINECS(EC#)]
664-233-5 | [Molecular Formula]
C7H6N2 | [MDL Number]
MFCD06738911 | [Molecular Weight]
118.14 | [MOL File]
271-29-4.mol |
| Chemical Properties | Back Directory | [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. ]
Keep in dark place,Inert atmosphere,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 Data | Back Directory | [Hazard Codes ]
Xi | [WGK Germany ]
WGK 3 | [Hazard Note ]
Irritant | [HS Code ]
29339980 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 | [Toxicity]
mouse,LD50,intraperitoneal,12mg/kg (12mg/kg),Journal of Medicinal Chemistry. Vol. 6, Pg. 480, 1963. |
| Hazard Information | Back Directory | [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 |
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