4-Azaindole supplier | CasNO.272-49-1

Name
4-Azaindole
EINECS 674-574-1
CAS No. 272-49-1
Article Data31
CAS DataBase
Density 1.242 g/cm³
Solubility Soluble in methanol and chloroform. Slightly soluble in water.
Melting Point 126-127 °C
Formula C₇H₆N₂
Boiling Point 273.782 °C at 760 mmHg
Molecular Weight 118.138
Flash Point 124.839 °C
Transport Information
Appearance White to off-white crystalline powder
Safety 26-39
Risk Codes 41
Molecular Structure
Hazard Symbols Xi
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;
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

Conditions	Yield
With potassium carbonate In methanol	100%

: 947330-64-5
2-((trimethylsilyl)ethynyl)pyridin-3-amine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
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

Conditions	Yield
With hydrogen; palladium on activated charcoal	95%
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 ethanol	15 mg

: 123846-65-1
2-(3-nitropyridin-2-yl)acetonitrile

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
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 acid	68%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With formic acid; palladium 10% on activated carbon In methanol for 4h; Inert atmosphere;	71%
With hydrogen; palladium on activated charcoal	37%
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

Conditions	Yield
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

Conditions	Yield
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

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

: 1219095-87-0
tert-butyl N-(2-methylpyridin-3-yl)carbamate

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Stage #1: tert-butyl N-(2-methylpyridin-3-yl)carbamate With n-butyllithium In tetrahydrofuran; hexane at -15 - 0℃; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 0 - 20℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 45℃; Cooling;	40%

: 116286-64-7
N-(2-methyl-[3]pyridyl)-formamide

: 917-58-8
potassium ethoxide

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
at 350℃;

: 116286-64-7
N-(2-methyl-[3]pyridyl)-formamide

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
With potassium ethoxide at 350℃;

: 6298-19-7
2-chloro-3-aminopyridine

: 75-07-0
acetaldehyde

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
With potassium tert-butylate 1.) Et2O, NH3 liquid, -33 deg C, 2.) Et2O, NH3 liquid, irrad., -33 deg C, 100 min.; Yield given. Multistep reaction;

: 107479-62-9
2-(2,2-diethoxyethyl)-3-nitropyridine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal
Multi-step reaction with 2 steps 1: 80 percent / H2 / 5 percent Pd-C / ethanol / Ambient temperature 2: 56 percent / conc. HCl / ethanol / 1 h / Heating View Scheme

: 5470-18-8
2-Chloro-3-nitropyridine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 50 percent / triethylamine; CuI / Pd(PPh3)4 / acetonitrile / 4 h / 20 °C 2: 60 percent / tin(II) chloride dihydrate; NH4Cl / ethanol / 4 h / 60 °C 3: 70 percent / potassium tert-butoxide / 1-methyl-pyrrolidin-2-one / 5 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: NaH / dimethylformamide 1.2: 50 percent / dimethylformamide / 1 h 2.1: 86 percent / aq. HCl / 8 h / Heating 3.1: dimethylformamide / 4.25 h / 90 °C 4.1: 0.31 g / HCOOH / Pd/C / methanol / 4 h View Scheme
Multi-step reaction with 3 steps 1: 43 percent / K2CO3 / (PPh3)4Pd / dioxane / 48 h / Heating 2: dimethylformamide / 4.25 h / 90 °C 3: 0.31 g / HCOOH / Pd/C / methanol / 4 h View Scheme

: 107469-26-1
3-nitro-2-[2-(trimethylsilyl)ethynyl]pyridine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / tin(II) chloride dihydrate; NH4Cl / ethanol / 4 h / 60 °C 2: 70 percent / potassium tert-butoxide / 1-methyl-pyrrolidin-2-one / 5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: NaOEt / ethanol 2: 1.) H2; 2.) HCl / 1.) Pd/C View Scheme
Multi-step reaction with 3 steps 1: ethanol / 3 h / Heating 2: 80 percent / H2 / 5 percent Pd-C / ethanol / Ambient temperature 3: 56 percent / conc. HCl / ethanol / 1 h / Heating View Scheme

: 18699-87-1
2-methyl-3-nitropyridine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 4.25 h / 90 °C 2: 0.31 g / HCOOH / Pd/C / methanol / 4 h View Scheme
Multi-step reaction with 2 steps 1: 100 percent 2: 95 percent / H2 / Pd/C View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere 2: formic acid / palladium 10% on activated carbon / methanol / 4 h / Inert atmosphere View Scheme

: 64362-41-0
diethyl 2-(3-nitropyridin-2-yl)malonate

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / aq. HCl / 8 h / Heating 2: dimethylformamide / 4.25 h / 90 °C 3: 0.31 g / HCOOH / Pd/C / methanol / 4 h View Scheme

: 146336-73-4
(E)-2-(2-ethoxyetenyl)-3-nitropyridine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / H2 / W-2 Raney Ni / methanol 2: 88 percent / conc. HCl / methanol / 2 h / Heating View Scheme

: 39856-58-1
3-amino-2-bromopyridine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 58 percent / pyridine / 3 h / 0-10 deg C 2: CuI, Et3N / Pd(PPh3)2Cl2 / 100 - 110 °C 3: NaOEt / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / tetrahydrofuran / 6 h / 60 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran; acetonitrile / 2 h / 20 °C View Scheme

: 19755-53-4
2-bromo-3-nitropyridine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: CuI, Et3N / Pd(PPh3)2Cl2 / 100 - 110 °C 2: NaOEt / ethanol 3: 1.) H2; 2.) HCl / 1.) Pd/C View Scheme

: 112671-55-3
ethyl 2-bromo-3-pyridinecarbamate

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CuI, Et3N / Pd(PPh3)2Cl2 / 100 - 110 °C 2: NaOEt / ethanol / Heating View Scheme

: 15513-52-7
3-nitro-2,6-lutidine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / ZnCl2, N,N-dimethylformamide / 24 h / 100 °C 2: 1.) ozonized oxygen, 2.) hydrogen peroxide 3: 100 percent 4: 95 percent / H2 / Pd/C View Scheme

: 142078-31-7
2-methyl-3-nitro-6-styrylpyridine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) ozonized oxygen, 2.) hydrogen peroxide 2: 100 percent 3: 95 percent / H2 / Pd/C View Scheme

: 3430-10-2
2-methyl-3-pyridinamine

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; acetic acid anhydride 2: potassium ethylate / 350 °C View Scheme

: 18699-87-1
2-methyl-3-nitropyridine

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

A: 3430-10-2
2-methyl-3-pyridinamine

B: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Stage #1: 2-methyl-3-nitropyridine; N,N-dimethyl-formamide dimethyl acetal In N,N-dimethyl-formamide at 120℃; for 17h; Stage #2: With palladium 10% on activated carbon; hydrogen In methanol; formic acid for 23h;

...Expand

: dimethyl 2-(3-nitropyridin-2-yl)malonate

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 8 h / Reflux 2: N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere 3: formic acid / palladium 10% on activated carbon / methanol / 4 h / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 8 h / Reflux 2: N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere 3: palladium 10% on activated carbon; formic acid / methanol / 4 h / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 8 h / Reflux 2: N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere 3: palladium 10% on activated carbon; formic acid / methanol / 4 h / Inert atmosphere View Scheme

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 5292-43-3
bromoacetic acid tert-butyl ester

: tert-butyl 2-(1H-pyrrolo[3,2-b]pyridin-1-yl)acetate

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 1h;	100%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 24424-99-5
di-tert-butyl dicarbonate

: 1018950-15-6
1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester

Conditions

Conditions	Yield
With dmap In acetonitrile at 20℃; for 3h; Inert atmosphere;	100%
In tetrahydrofuran at 20℃; for 48h;	99%
With dmap; triethylamine In dichloromethane at 20℃;	95%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: (2-bromoethoxy)triethylsilane

: 1018950-17-8
1-(2-(triethylsilyloxy)ethyl)-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 1h;	100%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 1116136-36-7
1H-pyrrolo[3,2-b]pyridine 4-oxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 72h;	100%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃;	88%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	70%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 1083181-26-3
3-iodo-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
With N-iodo-succinimide In tetrahydrofuran at 20℃;	100%
With iodine; potassium iodide In ethanol; water at 20℃; for 4h;	98%
With N-iodo-succinimide In tetrahydrofuran at 20℃;	93.5%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 50-00-0
formaldehyd

: 506-59-2
N,N-dimethylammonium chloride

: 23612-34-2
N,N-dimethyl-1-(1H-pyrrolo[3,2-b]pyridin-3-yl)methanamine

Conditions

Conditions	Yield
In butan-1-ol for 3h; Reflux;	99%
In water; butan-1-ol for 3h; Reflux;
In water; butan-1-ol at 120℃; for 3h;

...Expand

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 1-(3-bromo-2,2-dimethoxypropoxy)-4-octylbenzene

: 1-[2,2-dimethoxy-3-(4-octylphenoxy)propyl]-1H-4-azaindole

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In N,N-dimethyl-formamide for 5h; Reflux;	99%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 79099-07-3
N-tert-butyloxycarbonylpiperidin-4-one

: tert-butyl 4-(1H-pyrrolo[3,2-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Conditions

Conditions	Yield
With potassium hydroxide In methanol Heating / reflux;	98%
With potassium hydroxide In methanol Heating;

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 773-64-8
2-mesitylenesulphonyl chloride

: 1417718-50-3
1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 25℃; for 16h; Inert atmosphere;	96%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h;	96%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: C7H5(2)HN2

Conditions

Conditions	Yield
With water-d2; silver trifluoromethanesulfonate In chloroform-d1 at 90℃; for 18h; regioselective reaction;	95%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 98-09-9
benzenesulfonyl chloride

: 677302-44-2
1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 20℃;	94%
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 20℃; for 4.25h;	57.7%
With triethylamine In tetrahydrofuran

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 98-59-9
p-toluenesulfonyl chloride

: 1116136-30-1
1-tosyl-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 4h;	91%
With dmap; tetra(n-butyl)ammonium hydrogen sulfate; triethylamine In dichloromethane at 20℃; for 26h;	90%
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 20℃; for 3.5h;
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.16667h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran for 16h;

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 434-45-7
1,1,1-trifluoroacetophenone

: 2,2,2-trifluoro-1-phenyl-1-(1H-pyrrolo[3,2-b]pyridin-3-yl)ethan-1-ol

Conditions

Conditions	Yield
With tetrabutyl phosphonium bromide; potassium carbonate In water at 20℃; for 12h; regioselective reaction;	91%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 645-96-5
Benzeneselenol

: 3-(phenylselanyl)-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 27℃; for 2h;	90%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 23688-47-3
3-bromo-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 0.5h;	89%
With water; sodium bisulfate hydrate; sodium bromide In acetonitrile for 54h; Irradiation;	81%
With sodium hydrogensulfate monohydrate; water; sodium bromide In acetonitrile at 20℃; for 54h; Schlenk technique; Irradiation; Green chemistry;	81%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 100-97-0
hexamethylenetetramine

: 276862-85-2
1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde

Conditions

Conditions	Yield
With water; acetic acid for 4h; Reflux;	89%
With water; acetic acid for 6h; Reflux;	79%
With acetic acid In water for 4h; Heating / reflux;	56%
With water; acetic acid Duff Aldehyde Synthesis; Inert atmosphere; Reflux;

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 23612-33-1
3-nitro-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sulfuric acid; nitric acid at 0℃; for 2h; Stage #2: With sodium hydroxide In water pH=7 - 8;	89%
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sulfuric acid; nitric acid at 0℃; for 2h; Stage #2: With sodium hydroxide In water pH=7 - 8;	89%
With sulfuric acid at 0℃; for 4h;	80%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 645-00-1
m-iodonitrobenzene

: 1-(3-nitrophenyl)-1H-pyrrolo[3,2-c]pyridine

Conditions

Conditions	Yield
With potassium phosphate; copper In dimethyl sulfoxide at 80℃; for 5h; Inert atmosphere;	89%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 1-(1-phenylvinyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate

: 1-[(E)-styryl]pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine; 1-(1-phenylvinyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate In dimethyl sulfoxide at 21℃; for 0.0333333h; Schlenk technique; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 21℃; for 12h; Schlenk technique; regioselective reaction;	87%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 107112-93-6
dihydro-6,7 thieno<3,2-c>pyridine

: 3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-4-yl)-4-azaindole

Conditions

Conditions	Yield
In neat (no solvent) at 100℃; for 2h; Temperature; Microwave irradiation;	85%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 1570135-64-6
N-(2-(4,5-dihydrooxazol-2-yl)-phenyl)-1-methyl-1H-indole-2-carboxamide

: N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-1-methyl-3-(1H-pyrrolo[3,2-b]pyridin-1-yl)-1H-indole-2-carboxa mide

Conditions

Conditions	Yield
With potassium acetate; copper diacetate at 80℃; for 12h; Schlenk technique; Sealed tube;	85%
With copper diacetate; sodium carbonate In dimethyl sulfoxide at 80℃; for 2h; Sealed tube;	85%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 74-88-4
methyl iodide

: 153374-33-5
1-methyl-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 5℃; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	84.5%
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;	83%
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran for 24h;	31%
In N,N-dimethyl-formamide
Stage #1: 1H-pyrrolo[3,2-b]pyridine With Tris(3,6-dioxaheptyl)amine; potassium tert-butylate In toluene at 20℃; for 5h; Stage #2: methyl iodide In toluene at 20℃; for 24h;

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 4746-97-8
cyclohexanedione monoethylene ketal

: 1209481-93-5
3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
With potassium hydroxide In methanol Reflux; Inert atmosphere; Schlenk technique;	84%
With potassium hydroxide In methanol for 4h; Reflux;

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 106-95-6
allyl bromide

: 1-allyl-3-bromo-1H-pyrrolo[3,2-b]pyridine

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium bromide In acetonitrile at 20℃; for 2h; Electrolysis; Inert atmosphere; Green chemistry;	84%

: 272-49-1
1H-pyrrolo[3,2-b]pyridine

: 98-09-9
benzenesulfonyl chloride

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

Conditions

Conditions	Yield
Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In dimethyl sulfoxide for 0.25h; Stage #2: benzenesulfonyl chloride for 0.5h;	83%

4-Azaindole Chemical Properties

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

4-Azaindole 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.

4-Azaindole Safety Profile

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

4-Azaindole 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.

Product Name

4-Azaindole

Synthetic route

4-Azaindole Chemical Properties

4-Azaindole Toxicity Data With Reference

4-Azaindole Safety Profile

4-Azaindole Specification

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