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| CAS No.: | 15861-24-2 |
|---|---|
| Name: | 5-Cyanoindole |
| Article Data: | 76 |
| Molecular Structure: | |
|
|
|
| Formula: | C9H6N2 |
| Molecular Weight: | 142.16 |
| Synonyms: | 5-Cyanoindol;5-cyano indole;5-Cyano-1H-indole;1H-Indole-5-carbonitrile; |
| EINECS: | 239-986-4 |
| Density: | 1.24 g/cm3 |
| Melting Point: | 106-108 °C(lit.) |
| Boiling Point: | 350 °C at 760 mmHg |
| Flash Point: | 121.9 °C |
| Solubility: | Soluble in chloroform, hexane and methanol. Insoluble in water. |
| Appearance: | off-white crystalline powder |
| Hazard Symbols: |
 Xn;  Xi
|
| Risk Codes: | 36/37/38-20/21/22 |
| Safety: | 26-36-22 |
| PSA: | 39.58000 |
| LogP: | 2.03958 |
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| Conditions | Yield |
|---|---|
| With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate In tetrahydrofuran; water at 40℃; for 18h; Inert atmosphere; | 99% |
| With 1,1'-bis-(diphenylphosphino)ferrocene; palladium 10% on activated carbon; zinc(II) formate dihydrate In N,N-dimethyl acetamide at 110℃; for 12h; Inert atmosphere; | 90% |
- 174500-89-1
5-cyanoindole-3-carboxylic acid
- 15861-24-2
1H-indole-5-carbonitrile
| Conditions | Yield |
|---|---|
| With potassium carbonate In ethanol at 140℃; Schlenk technique; | 99% |
- 412947-51-4
4-amino-3-ethynylbenzonitrile
- 15861-24-2
1H-indole-5-carbonitrile
| Conditions | Yield |
|---|---|
| With P(p-C6H4F)3; chloro(1,5-cyclooctadiene)rhodium(I) dimer In N,N-dimethyl-formamide at 85℃; for 2h; | 98% |
| With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) In pyridine at 90℃; for 0.5h; Inert atmosphere; regioselective reaction; | 98% |
| With pyridine; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 90℃; for 0.5h; Catalytic behavior; Inert atmosphere; regioselective reaction; | 98% |
- 475102-10-4
1-(tert-butoxycarbonyl)-1H-indole-5-carbonitrile
- 15861-24-2
1H-indole-5-carbonitrile
| Conditions | Yield |
|---|---|
| In various solvent(s) at 150℃; for 0.0833333h; microwave irradiation; | 98% |
| With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 0.0833333h; Product distribution / selectivity; Microwave irradiation; | 98% |
| With 2,2,2-trifluoroethanol at 150℃; for 1h; Product distribution / selectivity; Microwave irradiation; | 98% |
| With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 0.0833333h; Product distribution / selectivity; Microwave irradiation; | 98% |
| Conditions | Yield |
|---|---|
| palladium diacetate; PS-triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 0.833333h; Irradiation; microwave; | 96% |
- 96784-54-2
3-methyl-4-nitrobenzonitrile
- 4637-24-5
N,N-dimethyl-formamide dimethyl acetal
- 15861-24-2
1H-indole-5-carbonitrile
| Conditions | Yield |
|---|---|
| Stage #1: 3-methyl-4-nitrobenzonitrile; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In dichloromethane at 50 - 55℃; for 8h; Large scale; Green chemistry; Stage #2: With iron; acetic acid In methanol at 0 - 55℃; for 8h; Reagent/catalyst; Solvent; Temperature; Large scale; Green chemistry; | 96% |
| Stage #1: 3-methyl-4-nitrobenzonitrile; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In 1,4-dioxane at 102℃; for 2.5h; Leimgruber-Batcho Indole Synthesis; Reflux; Inert atmosphere; Stage #2: With hydrazine hydrate In 1,4-dioxane at 45℃; for 1h; Leimgruber-Batcho Indole Synthesis; | 71% |
| Conditions | Yield |
|---|---|
| With copper(l) iodide; potassium iodide; N,N`-dimethylethylenediamine In toluene at 110℃; for 24h; Rosenmund-von Braun reaction; | 95% |
| Stage #1: 5-bromo-1H-indole; sodium cyanide With potassium iodide; N,N`-dimethylethylenediamine; copper(l) iodide In toluene at 110℃; for 24h; Stage #2: With ammonia In water; ethyl acetate; toluene at 25℃; for 0.166667h; | 95% |
| With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In various solvent(s) at 115℃; for 2h; Substitution; | 76% |
| Conditions | Yield |
|---|---|
| With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In acetonitrile for 2.5h; Reflux; | 95% |
| With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation; | 53% |
| Conditions | Yield |
|---|---|
| With 1,4-diaza-bicyclo[2.2.2]octane; copper(I) oxide; phenylsilane; ammonia In 1-methyl-pyrrolidin-2-one at 180℃; under 2280.15 Torr; for 24h; Sealed tube; chemoselective reaction; | 94% |
| With ammonia; hydrogen; nickel dibromide In N,N-dimethyl-formamide at 160℃; for 10h; Sealed tube; | 92 %Chromat. |
- 80531-13-1
1-benzyl-1H-indole-5-carbonitrile
- 15861-24-2
1H-indole-5-carbonitrile
| Conditions | Yield |
|---|---|
| With potassium tert-butylate; oxygen; dimethyl sulfoxide at 0℃; for 0.333333h; | 93% |
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Specification
The 5-Cyanoindole, with the CAS registry number 15861-24-2 and EINECS registry number 239-986-4, has the systematic name and IUPAC name of 1H-indole-5-carbonitrile. And the molecular formula of this chemical is C9H6N2. It is a off-white crystalline powder which is sensitive to light and air, and it should be stored at 0-6°C. What's more, it is used as medicine intermediate and inhibitor of enzyme.
The physical properties of 5-Cyanoindole are as following:
(1)ACD/LogP: 2.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.36; (4)ACD/LogD (pH 7.4): 2.36; (5)ACD/BCF (pH 5.5): 36.55; (6)ACD/BCF (pH 7.4): 36.55; (7)ACD/KOC (pH 5.5): 457.47; (8)ACD/KOC (pH 7.4): 457.47; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 28.72 Å2; (13)Index of Refraction: 1.674; (14)Molar Refractivity: 42.8 cm3; (15)Molar Volume: 113.9 cm3; (16)Polarizability: 16.96×10-24cm3; (17)Surface Tension: 61.5 dyne/cm; (18)Density: 1.24 g/cm3; (19)Flash Point: 121.9 °C; (20)Enthalpy of Vaporization: 59.46 kJ/mol; (21)Boiling Point: 350 °C at 760 mmHg; (22)Vapour Pressure: 4.51E-05 mmHg at 25°C.
Uses of 5-Cyanoindole:
It can react with 2-fluoro-pyridine to produce 5-cyano-N-(2-pyridyl)indole. This reaction will need reagent sodium hydride, and the solvent dimethylformamide. The reaction time is 2 hours with temperature of 95-100°C, and the yield is about 88%.
Safety information of 5-Cyanoindole:
You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin, and it is also harmful by inhalation, in contact with skin and if swallowed. Therefore, you had better take the following instructions: Do not breathe dust; Wear suitable protective clothing; In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: N#Cc1cc2c(cc1)ncc2
(2)InChI: InChI=1/C9H6N2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-5,11H
(3)InChIKey: YHYLDEVWYOFIJK-UHFFFAOYAP
The toxicity data of 5-Cyanoindole is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#12275, |