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| CAS No.: | 271-63-6 |
|---|---|
| Name: | 7-Azaindole |
| Article Data: | 65 |
| Molecular Structure: | |
|
|
|
| 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 |
| Appearance: | brown-cyrstalline solid |
| Hazard Symbols: |
 Xi, Xn
|
| Risk Codes: | 36-41-37/38-22 |
| Safety: | 39-26-36/37/39 |
| PSA: | 28.68000 |
| LogP: | 1.56290 |
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- 138343-77-8
1-(tert-butoxycarbonyl)-1H-pyrrolo<2,3-b>pyridine
- 271-63-6
7-Azaindole
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With hydrogenchloride In methanol for 2h; Heating; | 94% |
- 65326-33-2
1-(2-amino-3-pyridinyl)-1-ethanone
- 271-63-6
7-Azaindole
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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; |
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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: 
Xi, 
Xn
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.