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271-63-6

Basic Information
CAS No.: 271-63-6
Name: 7-Azaindole
Article Data: 65
Cas Database
Molecular Structure:
Molecular Structure of 271-63-6 (7-Azaindole)
Formula: C7H6N2
Molecular Weight: 118.138
Synonyms: 1,7-Dideazapurine;7H-Pyrrolo(2,3-b)pyridine;7-Aza-1-pyrindine;2,9-diazabicyclo[4.3.0]nona-2,4,7,10-tetraene;7H-Pyrrolo[2, 3-b]pyridine;7-Azaindole 98%;7-Azaindole,1H-Pyrrolo[2,3-b]pyridine;
EINECS: 205-981-0
Density: 1.242 g/cm3
Melting Point: 105-107 °C(lit.)
Boiling Point: 273.8 °C at 760 mmHg
Flash Point: 124.8 °C
Solubility: N/A
Appearance: brown-cyrstalline solid
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 36-41-37/38-22
Safety: 39-26-36/37/39
Transport Information: N/A
PSA: 28.68000
LogP: 1.56290
Synthetic route
138343-77-8

1-(tert-butoxycarbonyl)-1H-pyrrolo<2,3-b>pyridine

271-63-6

7-Azaindole

Conditions
ConditionsYield
With sodium carbonate In 1,2-dimethoxyethane; water for 20h; Heating;100%
With water at 100℃; for 1h;99%
With potassium phosphate In methanol at 120℃; under 5171.62 Torr; for 0.0333333h; Microwave irradiation;98%
138343-75-6

tert-butyl (3-methylpyridin-2-yl)carbamate

271-63-6

7-Azaindole

Conditions
ConditionsYield
Stage #1: tert-butyl (3-methylpyridin-2-yl)carbamate With n-butyllithium; N,N-dimethyl-formamide In tetrahydrofuran at 0℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 50℃;
100%
With n-butyllithium In tetrahydrofuran; hexane; N,N-dimethyl-formamide at -15 - 25℃; for 17.5h;3.8 g
Stage #1: tert-butyl (3-methylpyridin-2-yl)carbamate With trimethylsilyl bromide In tetrahydrofuran; N,N-dimethyl-formamide at -30℃; for 1.75h; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; water; N,N-dimethyl-formamide at 0 - 40℃; for 3h;
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / 4 h / 0 °C
1.2: 0 °C
2.1: hydrogenchloride / water / 8 h / Reflux
View Scheme
74-83-9

methyl bromide

138343-75-6

tert-butyl (3-methylpyridin-2-yl)carbamate

271-63-6

7-Azaindole

Conditions
ConditionsYield
Stage #1: methyl bromide; tert-butyl (3-methylpyridin-2-yl)carbamate In diethyl ether at 0℃; for 4h;
Stage #2: With N,N-dimethyl-formamide In diethyl ether at 0℃; for 0.5h; Concentration;
99.1%
10592-27-5

7-azaindoline

271-63-6

7-Azaindole

Conditions
ConditionsYield
With carbon dioxide; DBN; Eosin Y In dimethyl sulfoxide at 25 - 30℃; for 48h; Irradiation;97%
With potassium tert-butylate In decane at 150℃; for 36h; Inert atmosphere; Schlenk technique;90%
With 4-tert-Butylcatechol; oxygen In water at 20℃; for 20h; Green chemistry;90%
146336-83-6

(Z)-2-amino-3-(2-ethoxyethenyl)pyridine

271-63-6

7-Azaindole

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Heating;94%
65326-33-2

1-(2-amino-3-pyridinyl)-1-ethanone

271-63-6

7-Azaindole

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 90℃; pH=3; Temperature; pH-value; Microwave irradiation;93.2%
143141-23-5

1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine

271-63-6

7-Azaindole

Conditions
ConditionsYield
With sodium t-butanolate In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;93%
136818-50-3

7-azaindole-2-carboxylic acid

271-63-6

7-Azaindole

Conditions
ConditionsYield
With zinc(II) oxide In toluene at 90℃; for 2h; Temperature;91.8%
55052-24-9

1H-Pyrrolo[2,3-b]pyridine-7-oxide

271-63-6

7-Azaindole

Conditions
ConditionsYield
With (4,4′-di-tert-butyl-2,2′-bipyridine)bis[(2-pyridinyl)phenyl]iridium(III) hexafluorophosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 2h; Inert atmosphere; Irradiation; chemoselective reaction;91%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In dichloromethane at 31℃; for 16h; Sealed tube; Irradiation;83%
With styrene; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; hydrazine hydrate In dimethyl sulfoxide at 20℃; for 13h; Inert atmosphere; Irradiation; chemoselective reaction;74%
348640-02-8

1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine

271-63-6

7-Azaindole

Conditions
ConditionsYield
With cetyltrimethylammonim bromide; potassium hydroxide In tetrahydrofuran; water for 10h; Reagent/catalyst; Temperature; Time; Reflux; Green chemistry;90%
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Darkness; Schlenk technique;87%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;70%
With caesium carbonate In tetrahydrofuran; methanol at 22℃; for 2h;
Raw Materials
271-63-6
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Chemistry

Molecule structure of 7-Azaindole (CAS NO.271-63-6):

IUPAC Name: 1H-Pyrrolo[2,3-b]pyridine 
Molecular Weight: 118.13594 g/mol
Molecular Formula: C7H6N2 
Density: 1.242 g/cm3 
Melting Point: 105-107 °C(lit.)
Boiling Point: 273.8 °C at 760 mmHg 
Flash Point: 124.8 °C
Index of Refraction: 1.696
Molar Refractivity: 36.61 cm3
Molar Volume: 95 cm3
Polarizability: 14.51×10-24 cm3
Surface Tension: 60.1 dyne/cm
Enthalpy of Vaporization: 49.15 kJ/mol
Vapour Pressure: 0.0094 mmHg at 25 °C
XLogP3: 1.8
H-Bond Donor: 1
H-Bond Acceptor: 1
Tautomer Count: 2
Exact Mass: 118.053098
MonoIsotopic Mass: 118.053098
Topological Polar Surface Area: 28.7
Heavy Atom Count: 9
Canonical SMILES: C1=CC2=C(NC=C2)N=C1
InChI: InChI=1S/C7H6N2/c1-2-6-3-5-9-7(6)8-4-1/h1-5H,(H,8,9)
InChIKey: MVXVYAKCVDQRLW-UHFFFAOYSA-N
EINECS: 205-981-0
Product Categories: blocks; IndolesOxindoles; Heterocycles; Heterocycles series; Indole; Heterocyclic Compounds; Indole Series; Indole Derivatives; Pharmaceutical intermediate

Uses

 7-Azaindole (CAS NO.271-63-6) is used for organic synthetic reagent.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 490mg/kg (490mg/kg)   Journal of Medicinal Chemistry. Vol. 6, Pg. 480, 1963.

Safety Profile

Hazard Codes: IrritantXi, HarmfulXn
Risk Statements: 36-41-37/38-22 
R36:Irritating to eyes. 
R41:Risk of serious damage to the eyes. 
R37/38:Irritating to respiratory system and skin. 
R22:Harmful if swallowed.
Safety Statements: 39-26-36/37/39 
S39:Wear eye / face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
RTECS: UY8710000
HazardClass: IRRITANT
HS Code: 29339990 

Specification

 7-Azaindole (CAS NO.271-63-6) is also named as 1,7-Diazaindene ; 1,7-Dideazapurine ; 7-Aza-1-pyrindine ; 7H-Pyrrolo(2,3-b)pyridine ; NSC 67063 ; 1H-Pyrrolo(2,3-b)pyridine . 7-Azaindole (CAS NO.271-63-6) is brown-cyrstalline solid.