16136-52-0

Basic information

• Product Name: 4-Cyanoindole
• Synonyms: 1H-INDOL-4-AMINE;1H-INDOL-4-YLAMINE;4-CYANOINDOLE;4-AMINO-1H-INDOLE;INDOLE-4-AMINE;INDOLE-4-CARBONITRILE;4-Cyanoindoline;4-Cyanoindole, 97+%
• CAS NO: 16136-52-0
• Molecular Formula: C₉H₆N₂
• Molecular Weight: 142.16
• EINECS: 1308068-626-2
• Product Categories: blocks;Carboxes;IndolesOxindoles;Indoles and derivatives;Indole;Indoles;Simple Indoles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 16136-52-0.mol

Chemical Properties

• Melting Point: 117-121 °C(lit.)
• Boiling Point: 350 °C at 760 mmHg
• Flash Point: 121.9 °C
• Appearance: Off-white to pale brown/Solid
• Density: 1.24 g/cm³
• Vapor Pressure: 4.51E-05mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: −20°C
• PKA: 15.17±0.30(Predicted)
• Water Solubility: Soluble in water.
• CAS DataBase Reference: 4-Cyanoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cyanoindole(16136-52-0)
• EPA Substance Registry System: 4-Cyanoindole(16136-52-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-43-41-37/38-22
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• WGK Germany: 3
• F: 8-10-34
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 16136-52-0(Hazardous Substances Data)

Usage

Uses

4-Cyanoindole is used as a synthetic intermediate.

InChI:InChI=1/C9H6N2/c10-6-7-2-1-3-9-8(7)4-5-11-9/h1-5,11H

Upstream product

• 52488-36-5 4-bromo-1H-indole 
• 1443-60-3 tetrazolo<5,1-a>isoquinoline 
• 117719-59-2 3-acetyl-4-cyanoindole 
• 25235-85-2 4-chloro-1H-indole 
• 57-13-6 urea 
• 77287-34-4 formamide 
• 109-74-0 propyl cyanide 
• 2380-94-1 1H-indol-4-ol 
• 1259448-37-7 4-(trimethylsilyl)-1H-indol-5-yl trifluoromethanesulfonate 
• 36892-19-0 (2-chloro-6-nitro-phenyl)-pyruvic acid 
• 83-42-1 6-chloro-2-nitrotoluene 
• 71516-35-3 2-methyl-3-nitrobenzonitrile 
• 235-25-6 tetrazolo[1,5-a]quinoline 
• 75275-88-6 2-azidoquinoline 

Downstream Products

• 1345724-43-7 7-(1-benzyl-1H-indol-4-yl)-5-morpholin-4-yl-1,6-naphthyridine 
• 1345724-42-6 7-(1-benzyl-1H-indol-4-yl)-5-chloro-1,6-naphthyridine 
• 177548-00-4 1-benzyl-1H-indole-4-carbonitrile 
• 31271-86-0 1-[(4-methylphenyl)sulfonyl]-1H-indole-4-carbonitrile 
• 1313236-82-6 9-(quinoxalin-2-yl)-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one 
• 1313236-80-4 1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one trifluoroacetate 
• 1313236-77-9 tert-butyl 2-oxo-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecane-9-carboxylate 
• 1313236-75-7 tert-butyl 2-oxo-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undec-3-ene-9-carboxylate 
• 1313236-73-5 tert-butyl 4-allyl-4-(N-((1-tosyl-1H-indol-4-yl)methyl)acrylamido)piperidine-1-carboxylate 
• 1313236-71-3 tert-butyl 4-allyl-4-((1-tosyl-1H-indol-4-yl)methylamino)piperidine-1-carboxylate 
• 1145678-74-5 (1-tosyl-1H-indol-4-yl)methanamine 
• 1313236-98-4 9-(benzo[d]oxazol-2-yl)-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one 
• 1186663-64-8 3-Bromo-1H-indole-4-carbonitrile 
• 3468-18-6 1H-indole-4-methanamine 

Relevant articles and documents

C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(i)-Pd(ii) catalysisvs.Pd(ii) catalysis

Efficient C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles have been developed. The former route enables C4-arylation in a highly efficient and mild manner and the latter route provides an alternative straightforward protocol for synthesis of C2/C4 disubstituted indoles. The mechanism studies imply that the different reaction pathways were tuned by the distinct acid additives, which led to either the Pd(i)-Pd(ii) pathway or Pd(ii) catalysis.

Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species

Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.

Decarboxylation of indole-3-carboxylic acids under metal-free conditions

Two reaction systems have been developed for the decarboxylation of indole-3-carboxylic acids. The decarboxylation can be achieved smoothly under K2CO3-catalyzed or acetonitrile-promoted basic conditions. It provided an efficient and simple method for the transformation of indole-3-carboxylic acids and the corresponding indoles were isolated with good to excellent yields. From the experimental facts, we put forward the possible reaction mechanism.

A carboxamide is the cyanogen source of aromatic nitrile to the preparation method of the (by machine translation)

The invention discloses a method for preparing aromatic nitrile, is under the action of the nickel catalyst, in order to carboxamide is the cyanogen source, and with various substituents haloarene coupled reactions, preparing aromatic nitrile. The reaction temperature is 100 - 160 °C, the reaction time is 6 - 24 hours. It overcomes the traditional aromatic nitrile of the synthesis method operation of complex steps, requires the use of a toxic, more expensive, functionalization of the cyanogen source as the reaction raw material and the like. Compared with the traditional method, this method is simple to use cheap, green non-toxic of the formamide is cyano sources; without the need of external dehydrating agent, formamide in the nickel catalyst of the catalytic dehydration at the same time, with a nickel catalyst in coordination with the halogenated aromatic hydrocyanation, more economic, high-efficiency, environmental protection; at the same time the method exhibits good substrate universality, to air, moisture, light are not sensitive, high yield, product separation and purification is simple, with wide application. (by machine translation)

Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions

The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.

A indole compound and its preparation method and application (by machine translation)

The invention discloses a indole compound and its preparation method and application. The indole compounds of the structural formula such as formula (I) is shown. The indoles, rice galenical demonstrate the excellent inhibitory activity, the effect of most of the compound is obviously better than the positive control drug validamycin; especially compound I - 43, I - 44, I - 54, I - 73, II - 7 and II - 17, its galenical very good living body protection and treating effect, effect is better than the positive control; more specifically, compound I - 43 of the rice sheath blight bacteriostatic activity than validamycin activity is improved by nearly 300 times. The indole compounds in the prevention and/or treatment of rice sheath blight has great application prospects. In addition the compound of the invention is simple in construction, the preparation method is simple, and is suitable for large-scale industrial production. (I). (by machine translation)

Catalytic Cyanation Using CO2 and NH3

Li and co-workers describe the catalytic cyanation of organic halides with CO2 and NH3. In the presence of Cu2O/DABCO as the catalyst, a variety of aromatic bromides and iodides were transformed to the desired nitrile products with broad functional-group tolerance. Both 13C- and/or 15N-labeled nitriles were obtained conveniently with appropriately isotope-labeled CO2 and NH3. Construction of functionalized chemical compounds from small molecules in a highly selective and efficient manner is crucial for sustainable development. The chemical-based manufacturing sector of the future should aim to produce chemicals from very simple and abundant resources, just as nature uses CO2 and N2 to generate sugars, amino acids, and so forth. In practice, however, the utilization of CO2 for the generation of industrial products, such as drugs and related intermediates, still remains a major challenge. Here, we describe the facile cyanide-free production of high-value nitriles with CO2 and NH3 as the sole sources of carbon and nitrogen, respectively. This practical and catalytic methodology provides a unique strategy for the utilization of small molecules for sustainable and cost-effective applications. Selective cyanation of aryl halides was achieved with CO2 and NH3 as the only sources of carbon and nitrogen, respectively. In the presence of Cu catalysts under low pressure (3 atm), a variety of aromatic iodides and bromides were transformed to the desired nitrile products without the use of toxic metal cyanides. Notably, olefins, esters, amides, alcohols, and amino groups were tolerated. Mechanistic studies suggest that Cu(III)-aryl insertion by isocyanate intermediates is involved. [13C,15N]-labeled nitriles were conveniently accessible from the respective isotope-labeled CO2 and NH3 via this methodology.

Cyaniding method for preparing nitrile compound

The invention provides a cyaniding method for preparing a nitrile compound. Organic halide or pseudohalide, CO2 and NH3 which are low in price and are easily obtained and a reducing agent react, a selective cyaniding reaction is conducted in the presence of a transition metal catalyst, and the target product namely organic the nitrile compound is obtained. According to the cyaniding method for preparing the nitrile compound, a new reaction route is used, through a CO2 and NH3 reaction of metal catalysis, dehalogenation cyaniding or quasi halide cyaniding of halide or pseudohalide is directly achieved through a one-pot method, the problem is solved that a traditional cyanation reaction needs equivalent toxic cyanide, a new direct and convenient method for preparing isotope-labeled nitrile compounds is provided at the same time, and the method can be applied to medicine, tracing, biology and medicine research and development.

Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling

We describe a nickel-catalyzed cyanation reaction of aryl (pseudo)halides that employs butyronitrile as a cyanating reagent instead of highly toxic cyanide salts. A dual catalytic cycle merging retro-hydrocyanation and cross-coupling enables the conversion of a broad array of aryl chlorides and aryl/vinyl triflates into their corresponding nitriles. This new reaction provides a strategically distinct approach to the safe preparation of aryl cyanides, which are essential compounds in agrochemistry and medicinal chemistry.

Indolyne experimental and computational studies: Synthetic applications and origins of selectivities of nucleophilic additions

Efficient syntheses of 4,5-, 5,6-, and 6,7-indolyne precursors beginning from commercially available hydroxyindole derivatives are reported. The synthetic routes are versatile and allow access to indolyne precursors that remain unsubstituted on the pyrrole ring. Indolynes can be generated under mild fluoride-mediated conditions, trapped by a variety of nucleophilic reagents, and used to access a number of novel substituted indoles. Nucleophilic addition reactions to indolynes proceed with varying degrees of regioselectivity; distortion energies control regioselectivity and provide a simple model to predict the regioselectivity in the nucleophilic additions to indolynes and other unsymmetrical arynes. This model has led to the design of a substituted 4,5-indolyne that exhibits enhanced nucleophilic regioselectivity.