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272-49-1

Basic Information
CAS No.: 272-49-1
Name: 4-Azaindole
Article Data: 31
Cas Database
Molecular Structure:
Molecular Structure of 272-49-1 (4-Azaindole)
Formula: C7H6N2
Molecular Weight: 118.138
Synonyms: 5-23-06-00303 (Beilstein Handbook Reference);1H-Pyrrolo[3,2-b]pyridine;5,9-diazabicyclo[4.3.0]nona-2,4,7,10-tetraene;1H-Pyrrolo(3,2-b)pyridine;1,4-Diazaindene;
EINECS: 674-574-1
Density: 1.242 g/cm3
Melting Point: 126-127 °C
Boiling Point: 273.782 °C at 760 mmHg
Flash Point: 124.839 °C
Solubility: Soluble in methanol and chloroform. Slightly soluble in water.
Appearance: White to off-white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 41
Safety: 26-39
Transport Information: N/A
PSA: 28.68000
LogP: 1.56290
Synthetic route
24509-73-7

1-(1H-pyrrolo[3,2-b]pyridin-1-yl)ethanone

272-49-1

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

Conditions
ConditionsYield
With potassium carbonate In methanol100%
947330-64-5

2-((trimethylsilyl)ethynyl)pyridin-3-amine

272-49-1

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

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; acetonitrile at 20℃; for 2h;97%
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 20℃; for 5h;70%
65156-92-5

2-(3-nitro-2-pyridinyl)-N,N-dimethyletheneamine

272-49-1

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

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal95%
With formic acid; palladium 10% on activated carbon In methanol for 4h; Inert atmosphere;71%
With hydrogenchloride; iron In 1,4-dioxane; methanol at 80℃; for 3h;
With palladium 10% on activated carbon; hydrogen In ethanol15 mg
123846-65-1

2-(3-nitropyridin-2-yl)acetonitrile

272-49-1

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

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 24h;89%
With palladium 10% on activated carbon; hydrogen at 20℃; for 24h;85%
With hydrogen; sodium hydrogencarbonate; palladium In ethanol; water; acetic acid68%
With palladium 10% on activated carbon; hydrogen; acetic acid In ethanol at 20℃; under 2844.39 Torr; for 24h;68%
146336-81-4

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

272-49-1

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

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Heating;88%
849353-49-7

(2-trimethylsilanylethynylpyridin-3-yl) carbamic acid tert-butyl ester

272-49-1

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

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 8h; Heating / reflux;79%
65156-92-5

(E)-N,N-dimethyl-2-(3-nitropyridin-2-yl)ethenamine

272-49-1

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

Conditions
ConditionsYield
With formic acid; palladium 10% on activated carbon In methanol for 4h; Inert atmosphere;71%
With hydrogen; palladium on activated charcoal37%
With formic acid; palladium on activated charcoal In methanol for 4h;0.31 g
With formic acid; palladium 10% on activated carbon In methanol for 4h; Inert atmosphere;
With iron(III) chloride; hydrazine hydrate In methanol; water at 25 - 70℃;
150281-83-7

2-ethenyl-3-nitropyridine

272-49-1

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

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 1,10-Phenanthroline; carbon monoxide In acetonitrile at 120℃; under 4560.31 Torr; for 42h;65%
112671-57-5

(2-Trimethylsilanylethynyl-pyridin-3-yl)carbamic acid ethyl ester

272-49-1

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

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 1h; Heating / reflux;63.5%
With sodium ethanolate In ethanol for 1h; Heating / reflux;63.5%
With sodium ethanolate In ethanol Heating; Yield given;
107469-27-2

3-amino-2-(2,2-diethoxyethyl)pyridine

272-49-1

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

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 1h; Heating;56%
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Chemistry

Molecular Structure of 4-Azaindole (CAS No.272-49-1):

Molecular Formula: C7H6N2
Molecular Weight: 118.14
IUPAC Name: 1H-Pyrrolo[3,2-b]pyridine
CAS No: 272-49-1
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 0
Polar Surface Area: 28.68 Å2
Index of Refraction: 1.697
Molar Refractivity: 36.62 cm3
Molar Volume: 95.095 cm3
Surface Tension: 60.176 dyne/cm
Density: 1.242 g/cm3
Melting Point: 126-127°C
Flash Point: 124.839 °C
Enthalpy of Vaporization: 49.153 kJ/mol
Boiling Point: 273.782 °C at 760 mmHg
Vapour Pressure of 4-Azaindole (CAS No.272-49-1): 0.009 mmHg at 25°C
Classification Code: Drug/Therapeutic Agent
Product Categories: Indoles and derivatives;Indole;Heterocyclic Compounds;Indole Series;Indoles;Azaindole;Building Blocks
Solubility: Hardly soluble in water, but soluble in methanol and chloroform
Canonical SMILES: C1=CC2=C(C=CN2)N=C1
InChI: InChI=1S/C7H6N2/c1-2-6-7(8-4-1)3-5-9-6/h1-5,9H
InChIKey: XWIYUCRMWCHYJR-UHFFFAOYSA-N

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 260mg/kg (260mg/kg)   Journal of Medicinal Chemistry. Vol. 6, Pg. 480, 1963.

Safety Profile

Safety Information of 4-Azaindole (CAS No.272-49-1):
Hazard Codes: IrritantXi
Hazard Note: Irritant
HazardClass: IRRITANT

Specification

   4-Azaindole (CAS No.272-49-1), it also can be called 1H-Pyrrolo[3.2-b]pyridine ; 1,4-Diazaindene .It is white to off-white crystalline powder.Several 4-azaindole and 7-azaindole dimer analogues of melatonin with a bisalkoxyalkyl spacer between the position 5 of each heterocycle were synthetized. Results suggest the distance between indole ring seems to be an important parameter in determining the potency of binding with melatonin receptor site. Storage of 4-Azaindole: Keep container closed tightly, refrigerate (2-8°C), store dry, and protect from light.