5-Azaindole supplier | CasNO.271-34-1

Name
5-Azaindole
EINECS 676-348-8
CAS No. 271-34-1
Article Data36
CAS DataBase
Density 1.242 g/cm³
Solubility Hardly soluble in water. Soluble in methanol and chloroform.
Melting Point 104.6-108.4°C
Formula C₇H₆N₂
Boiling Point 295.8 °C at 760 mmHg
Molecular Weight 398.224
Flash Point 137.4 °C
Transport Information
Appearance off-white to yellowish crystalline powder
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 5-23-06-00304 (Beilstein Handbook Reference);1H-Pyrrolo[3,2-c]pyridine;4,9-diazabicyclo[4.3.0]nona-2,4,7,10-tetraene;1H-Pyrrolo(3,2-c)pyridine;3,7-Dideazapurine;1,5-Diazaindene;
PSA 28.68000
LogP 1.56290

Synthetic route

: 60290-21-3
4-chloro-1H-pyrrolo-[3,2-c]-pyridine

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	96%

: 148760-75-2
tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 1.5h;	95%

: 148760-46-7
3-(4-Morpholinovinylene)-4-nitropyridine 1-oxide

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With hydrogen; nickel In ethanol; water under 14.7 - 22.07 Torr; 1) 15 h, 20 deg C, 2) 3-5 h, 60 deg C;	92%

: 148760-47-8
3-Dimethylaminovinylene-4-nitropyridine

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 14.7 - 22.07 Torr; 1) 1 h, 20 deg C, 2) 3 h, 60 deg C;	91%

: 123367-22-6
(E)-N,N-dimethyl-2-(4-nitro-1-oxidopyridin-3-yl)ethenamine

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 60℃; under 3750.38 Torr; for 4h; Inert atmosphere;	91%
With hydrogen; palladium on activated charcoal In ethanol under 14.7 - 22.07 Torr; 1) 1 h, 20 deg C, 2) 3 h, 60 deg C;	87%
With hydrogen; Raney nickel In ethanol; water at 20 - 40℃; under 750.075 Torr; for 5.25h;	76%

: 19798-77-7
4-amino-3-chloropyridine

: 74-86-2
acetylene

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With Ni(1,5-cyclooctadiene)2 In tetrahydrofuran; diethyl ether at 110℃; for 4.5h; Temperature; Microwave irradiation;	90.4%

: 146336-80-3
N-(3-((Z)-2-ethoxyvinyl)pyridin-4-yl)acetamide

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;	90%
With hydrogenchloride In methanol; water for 5h; Inert atmosphere; Reflux;	1.9 g

raney's nickel: raney's nickel

: 3-(β-dimethylaminovinyl)-4-nitro-pyridine-1-oxide

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
In ethanol; water	84%

: 1239605-12-9
3-ethynyl-4-pyridinamine

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With pyrrolidine In water at 200℃; for 0.25h; Microwave irradiation;	82%

: 104118-88-9
3-dimethylaminovinylene-4-nitropyridine-l-oxide

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20 - 65℃; under 1500.15 - 2250.23 Torr; for 8h; Inert atmosphere; Autoclave;	74.5%

: 101870-39-7
N-(3-methyl-[4]pyridyl)-formamide

: 141-53-7
sodium formate

: 1865-45-8
sodium anilide

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
at 300℃;

...Expand

: 101870-39-7
N-(3-methyl-[4]pyridyl)-formamide

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With sodium formate; sodium anilide at 290 - 310℃;

: 119248-43-0
1H-pyrrole[3,2-C]pyridine-3-carboxylic acid

: 271-34-1
5-azaindole

: 112671-58-6
(3-Trimethylsilanylethynyl-pyridin-4-yl)-carbamic acid ethyl ester

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With sodium ethanolate In ethanol Heating; Yield given;

: 2-Hydroxy-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With hydrogenchloride at 45 - 50℃; for 1h; Yield given;

: 1074-98-2
3-methyl-4-nitropyridine N-oxide

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 90 °C 2: H2 / Pd/C / ethanol / 60 °C View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 20 - 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 60 °C / 3750.38 Torr / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 1.5 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 8 h / 20 - 65 °C / 1500.15 - 2250.23 Torr / Inert atmosphere; Autoclave View Scheme

: 98400-69-2
N-(4-pyridyl) t-butyl carbamate

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) BuLi / 1.) THF, hexane, 0 deg C, 3 h, 2.) THF, hexane, 20 deg C, 1 h 2: 1.) t-BuLi / 1.) THF, pentane, -40 deg C, 1 h, 2.) THF, pentane, 20 deg C, 1 h 3: 5.5 M HCl / 1 h / 45 - 50 °C View Scheme

: 180253-65-0
(3-methylpyridin-4-yl)carbamic acid tert-butyl ester

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) t-BuLi / 1.) THF, pentane, -40 deg C, 1 h, 2.) THF, pentane, 20 deg C, 1 h 2: 5.5 M HCl / 1 h / 45 - 50 °C View Scheme

: 13534-98-0
3-bromopyridin-4-amine

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: 93 percent / Pd(PPh3)2Cl2, Et4NCl / acetonitrile / 2.5 h / Heating 3: 90 percent / conc. HCl / methanol / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 52 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 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 5 - 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; tetrabutyl-ammonium chloride / acetonitrile / 2.5 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / Inert atmosphere; Reflux View Scheme

: 13535-03-0
N-(3-bromopyridin-4-yl)acetamide

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / Pd(PPh3)2Cl2, Et4NCl / acetonitrile / 2.5 h / Heating 2: 90 percent / conc. HCl / methanol / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; tetrabutyl-ammonium chloride / acetonitrile / 2.5 h / Inert atmosphere; Reflux 2: hydrogenchloride / methanol; water / 5 h / Inert atmosphere; Reflux View Scheme

: 1678-49-5
3-Bromo-4-nitropyridine N-oxide

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 75 percent / 20percent aq. TiCl3 / acetic acid / 25 h / Ambient temperature 3: 93 percent / Pd(PPh3)2Cl2, Et4NCl / acetonitrile / 2.5 h / Heating 4: 90 percent / conc. HCl / methanol / 2 h / Heating View Scheme

: 1678-53-1
3-Methyl-4-nitropyridine

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / dimethylformamide / 1 h / 90 °C 2: 91 percent / H2 / 10percent Pd/C / ethanol / 14.7 - 22.07 Torr / 1) 1 h, 20 deg C, 2) 3 h, 60 deg C View Scheme
Multi-step reaction with 3 steps 1: palladium; ethanol / Hydrogenation 2: THF 3: sodium anilide; sodium formate / 290 - 310 °C View Scheme

: 1074-98-2
3-methyl-4-nitropyridine N-oxide

zinc: zinc

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / PCl3 / 3.5 h / T < 0 deg C 2: 63 percent / dimethylformamide / 1 h / 90 °C 3: 91 percent / H2 / 10percent Pd/C / ethanol / 14.7 - 22.07 Torr / 1) 1 h, 20 deg C, 2) 3 h, 60 deg C View Scheme
Multi-step reaction with 2 steps 1: 92 percent / dimethylformamide / 2 h / 100 °C 2: 92 percent / H2 / Raney nickel / ethanol; H2O / 14.7 - 22.07 Torr / 1) 15 h, 20 deg C, 2) 3-5 h, 60 deg C View Scheme
Multi-step reaction with 2 steps 1: 96 percent / dimethylformamide / 1 h / 90 °C 2: 87 percent / H2 / 10percent Pd/C / ethanol / 14.7 - 22.07 Torr / 1) 1 h, 20 deg C, 2) 3 h, 60 deg C View Scheme

: 112671-56-4
ethyl (3-bromopyridin-4-yl)carbamate

: 271-34-1
5-azaindole

Conditions

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

: 26956-47-8
1-benzyl-4,5-dihydro-4-oxopyrrolo<3,2-c>pyridine

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 79 percent / Na, liquid ammonia 2: 78 percent / phosphorus oxychloride / 5 h / 180 °C 3: 96 percent / H2 / 10percent Pd/C / ethanol View Scheme

: 54415-77-9
4,5-dihydro-4-oxo-1H-pyrrolo<3,2-c>pyridine

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / phosphorus oxychloride / 5 h / 180 °C 2: 96 percent / H2 / 10percent Pd/C / ethanol View Scheme

: 1990-90-5, 953018-16-1
4-amino-3-methylpyridine

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: THF 2: sodium anilide; sodium formate / 290 - 310 °C View Scheme
Multi-step reaction with 3 steps 1: TiCl2(ClO4)2 / acetone / 1 h / 60 °C 2: salicylic acid; iron(II) oxide / N,N-dimethyl acetamide / 2 h / 70 °C 3: zinc(II) oxide / tetrachloromethane / 2 h / 90 °C View Scheme

: 765307-12-8
{[(3-Trimethylsilanyl)ethynyl]-pyridin-4-yl}amine

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With copper(I) iodide In N,N-dimethyl-formamide

: 1074-98-2
3-methyl-4-nitropyridine N-oxide

: 1188-33-6
N,N-dimethylformamide diethyl diacetal

: 271-34-1
5-azaindole

Conditions

Conditions	Yield
With sodium hydroxide; ammonium formate; palladium In ethanol; water; N,N-dimethyl-formamide; toluene; benzene

: 271-34-1
5-azaindole

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

: 148760-75-2
tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Conditions

Conditions	Yield
With dmap In acetonitrile at 20℃; for 18h;	100%
With triethylamine In dichloromethane at 25℃; for 12h; Inert atmosphere;	98.2%
With triethylamine In dichloromethane at 25℃; for 12h; Inert atmosphere;	98.2%

: 271-34-1
5-azaindole

: 501-53-1
benzyl chloroformate

: 1426255-11-9
benzyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	100%

: 271-34-1
5-azaindole

: 760947-12-4
6-bromo-4-chloro-2-(2-fluoro-phenyl)-quinazoline

: 760946-13-2
6-bromo-2-(2-fluoro-phenyl)-4-pyrrolo[3,2-c]pyridin-1-yl-quinazoline

Conditions

Conditions	Yield
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 1h;	98%

: 271-34-1
5-azaindole

: C7H5(2)HN2

Conditions

Conditions	Yield
With water-d2; silver trifluoromethanesulfonate In chloroform-d1 at 90℃; for 18h; regioselective reaction;	97%

: 271-34-1
5-azaindole

: 100-44-7
benzyl chloride

: N5-benzyl-5-azaindole

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 6h;	96%

: 271-34-1
5-azaindole

: 75-36-5
acetyl chloride

: 3-acetyl-5-azaindole

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane at 20℃; Friedel-Crafts reaction;	94%

: 271-34-1
5-azaindole

: 98-59-9
p-toluenesulfonyl chloride

: 1279863-30-7
1-tosyl-1H-pyrrolo[3,2-c]pyridine

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water; toluene at 0 - 10℃; for 2h; Inert atmosphere;	93%
Stage #1: 5-azaindole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.16667h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran for 15h;

: 271-34-1
5-azaindole

: 98-88-4
benzoyl chloride

: 3-benzoyl-5-azaindole

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane at 20℃; Friedel-Crafts reaction;	92%

: 271-34-1
5-azaindole

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

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

Conditions

Conditions	Yield
With tetrabutyl phosphonium bromide; potassium carbonate In water at 20℃; for 12h; regioselective reaction;	92%

: 271-34-1
5-azaindole

: 877060-47-4
3-iodo-1H-pyrrolo[3,2-c]pyridine

Conditions

Conditions	Yield
With potassium hydroxide; iodine In N,N-dimethyl-formamide at 20℃; for 0.25h;	91%
With iodine; potassium hydroxide regiospecific reaction;	87%
Stage #1: 5-azaindole With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: With iodine In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h;	83%
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃;	73%
Stage #1: 5-azaindole With potassium hydroxide In N,N-dimethyl-formamide at 25℃; for 0.25h; Stage #2: With iodine In N,N-dimethyl-formamide at 25℃; for 0.25h;

: 271-34-1
5-azaindole

: 15854-87-2
4-iodopyridine

: 1542750-10-6
1-(pyridin-4-yl)-1H-pyrrolo[3,2-c]pyridine

Conditions

Conditions	Yield
With potassium phosphate In dimethyl sulfoxide at 80℃; for 5h; Ullmann-Goldberg Substitution; Inert atmosphere;	90%
With potassium phosphate; copper In dimethyl sulfoxide at 80℃; for 5h; Ullmann-Goldberg Substitution; Inert atmosphere;	90%

: 271-34-1
5-azaindole

: 609-73-4
o-nitroiodobenzene

: 1542750-13-9
1-(2-nitrophenyl)-1H-pyrrolo[3,2-c]pyridine

Conditions

Conditions	Yield
With potassium phosphate; copper In dimethyl sulfoxide at 80℃; for 2h; Ullmann-Goldberg Substitution; Inert atmosphere;	89%
With potassium phosphate In dimethyl sulfoxide at 80℃; for 2h; Ullmann-Goldberg Substitution; Inert atmosphere;

: 271-34-1
5-azaindole

: 1829-28-3
ethyl 2-iodobenzoate

: C16H14N2O2

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 24h;	88%

: 271-34-1
5-azaindole

: 667-27-6
Ethyl bromodifluoroacetate

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

Conditions

Conditions	Yield
With carbon dioxide; potassium hydroxide In acetonitrile at 130℃; for 12h; Autoclave;	88%

: 271-34-1
5-azaindole

: 637-87-6
1-Chloro-4-iodobenzene

: C13H9ClN2

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 24h;	85%

: 271-34-1
5-azaindole

: 74-88-4
methyl iodide

: 1195996-58-7
5-methyl-1H-pyrrolo[3,2-c]pyridin-5-ium iodide

Conditions

Conditions	Yield
In toluene at 120℃; for 2h; Inert atmosphere;	85%

: 271-34-1
5-azaindole

: 106-54-7
p-Chlorothiophenol

: 3-((4-chlorophenyl)thio)-1H-pyrrolo[3,2-c]pyridine

Conditions

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 100℃; for 3h; Schlenk technique;	85%

: 271-34-1
5-azaindole

: 40400-13-3
2-Iodobenzyl bromide

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

Conditions

Conditions	Yield
Stage #1: 5-azaindole With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; Schlenk technique; Stage #2: 2-Iodobenzyl bromide In dimethyl sulfoxide at 20℃; Schlenk technique;	85%

: 271-34-1
5-azaindole

: 98-09-9
benzenesulfonyl chloride

: 109113-39-5
1-Benzenesulfonyl-1H-pyrrolo<3,2-c>pyridine

Conditions

Conditions	Yield
Stage #1: 5-azaindole With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 20℃;	84%
Stage #1: 5-azaindole With sodium hydride In mineral oil at 0℃; for 0.5h; Stage #2: benzenesulfonyl chloride at 0 - 20℃; for 1h;	69.4%
Stage #1: 5-azaindole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 0 - 20℃; for 1h;	69.4%

: 271-34-1
5-azaindole

: 773-64-8
2-mesitylenesulphonyl chloride

: 1417718-51-4
1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrolo[3,2-c]pyridine

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 25℃; for 16h; Inert atmosphere;	84%
With sodium hydride at 0 - 20℃; for 16h;	84%

: 271-34-1
5-azaindole

: (5-methoxy-3-indolylmethyl)trimethylammonium iodide

: 1-((5-methoxy-1H-indol-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridine

Conditions

Conditions	Yield
In water at 80℃; Sealed tube; Green chemistry; regioselective reaction;	84%

5-Azaindole Specification

The 5-Azaindole is an organic compound with the formula C₇H₆N₂. The IUPAC name of this chemical is 1H-pyrrolo[3,2-c]pyridine. With the CAS registry number 271-34-1, it is also named as 3,7-Dideazapurine. The product's categories are Indoles and Derivatives; Indole; Heterocyclic Compounds; Indole Series; Azaindole; Building Blocks. It is used as reagent for organic synthesis.

The other characteristics of 5-Azaindole can be summarized as: (1)ACD/LogP: 1.25; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 7.4): 0.392; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 15.855; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 0; (11)Index of Refraction: 1.697; (12)Molar Refractivity: 36.62 cm³; (13)Molar Volume: 95.095 cm³; (14)Polarizability: 14.517×10^-24 cm³; (15)Surface Tension: 60.176 dyne/cm; (16)Enthalpy of Vaporization: 51.406 kJ/mol; (17)Vapour Pressure: 0.003 mmHg at 25°C; (18)Tautomer Count: 2; (19)Exact Mass: 118.053098; (20)MonoIsotopic Mass: 118.053098; (21)Topological Polar Surface Area: 28.7; (22)Heavy Atom Count: 9; (23)Complexity: 103.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:c1c[nH]c2c1cncc2
2. InChI:InChI=1/C7H6N2/c1-4-9-7-2-3-8-5-6(1)7/h1-5,9H
3. InChIKey:SRSKXJVMVSSSHB-UHFFFAOYAQ
4. Std. InChI:InChI=1S/C7H6N2/c1-4-9-7-2-3-8-5-6(1)7/h1-5,9H
5. Std. InChIKey:SRSKXJVMVSSSHB-UHFFFAOYSA-N

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	16mg/kg (16mg/kg)		Journal of Medicinal Chemistry. Vol. 6, Pg. 480, 1963.

Product Name

5-Azaindole

Synthetic route

5-Azaindole Specification

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