2510-55-6

Usage

Chemical Properties

yellow-green powder

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 260, 1947 DOI: 10.1021/ja01194a027Organic Syntheses, Coll. Vol. 3, p. 212, 1955

InChI:InChI=1/C15H9N/c16-10-12-9-11-5-1-2-6-13(11)15-8-4-3-7-14(12)15/h1-9H

Upstream product

• 1140-01-8 (+/-)-(8ar,10ac)-1,2,3,4,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthrene-9c-carbonitrile 
• 506-68-3 bromocyane 
• 85-01-8 phenanthrene 
• 31603-73-3 bis(phenanthrene-1-ylmethylidene)hydrazine 
• 143-33-9 sodium cyanide 
• 98370-88-8 5-(phenanthren-9-yl)-2H-tetrazole 
• 67-56-1 methanol 
• 563-79-1 2,3-Dimethyl-2-butene 
• 91-15-6 phthalonitrile 
• 623-26-7 terephthalonitrile 
• 110-83-8 cyclohexene 
• 1128-65-0 [1,1']bicyclohexyl-1,1'-diene 
• 19472-74-3 2-(2-bromophenyl)acetonitrile 
• 40138-16-7 2-formylbenzene boronic acid 

Downstream Products

• 2510-60-3 phenanthrene-9-carboxamide 
• 4707-71-5 Phenanthrene-9-carboxaldehyde 
• 87884-71-7 N-n-propyl-9-phenanthrenamine 
• 75-31-0 isopropylamine 
• 82992-72-1 3-methoxy-2,3-dimethyl-but-1-ene 
• 52958-93-7 1,1,2,2-Tetramethyl-1,10b-dihydro-2H-cyclobuta[l]phenanthrene-2a-carbonitrile 
• 26356-10-5 2,3-dimethyl-2-butyl methyl ether 
• 82992-71-0 2,3,3,5,5,6-hexamethyl-6-methoxy-1-heptene 
• 79606-70-5 (1R,2S,2aS,10bR)-1,2-Di-p-tolyl-1,10b-dihydro-2H-cyclobuta[l]phenanthrene-2a-carbonitrile 
• 79606-70-5 (1S,2R,2aS,10bR)-1,2-Di-p-tolyl-1,10b-dihydro-2H-cyclobuta[l]phenanthrene-2a-carbonitrile 
• 79606-65-8 (1R,2S,2aS,10bR)-1,2-Bis-(4-methoxy-phenyl)-1,10b-dihydro-2H-cyclobuta[l]phenanthrene-2a-carbonitrile 
• 79606-69-2 (1R,2S,2aS,10bR)-2-(4-Methoxy-phenyl)-1-phenyl-1,10b-dihydro-2H-cyclobuta[l]phenanthrene-2a-carbonitrile 
• 79606-69-2 (1S,2R,2aS,10bR)-2-(4-Methoxy-phenyl)-1-phenyl-1,10b-dihydro-2H-cyclobuta[l]phenanthrene-2a-carbonitrile 
• 85-01-8 phenanthrene 

Relevant academic research and scientific papers

Antiproliferative activity and mode of action analysis of novel amino and amido substituted phenantrene and naphtho[2,1-b]thiophene derivatives

Herein we present and describe the design and synthesis of novel phenantrene derivatives substituted with either amino or amido side chains and their biological activity. Antiproliferative activities were assessed in vitro on a panel of human cancer cell lines. Tested compounds showed moderate activity against cancer cells in comparison with 5-fluorouracile. Among all tested compounds, some compounds substituted with cyano groups showed a pronounced and selective activity in the nanomolar range of inhibitory concentrations against HeLa and HepG2. The strongest selective activity against HeLa cells was observed for acrylonitriles 8 and 11 and their cyclic analogues 15 and 17 substituted with two cyano groups with a corresponding IC50 = 0.33, 0.21, 0.65 and 0.45 μM, respectively. Compounds 11 showed the most pronounced selectivity being almost non cytotoxic to normal fibroblasts. Additionally, mode of biological action analysis was performed in silico and in vitro by Western blot analysis of HIF-1-α relative expression for compounds 8 and 11.

Kinetic Analysis of Aromatic Photocyanation: Naphthalene, Biphenyl, and Phenanthrene

Nucleophilic photocyanation of the unsubstituted aromatic hydrocarbons, naphthalene, biphenyl, and phenanthrene, in both dry and aqueous acetonitrile can be described by a mechanism involving two photoinduced transients.The primary step of the mechanism is the formation of a transient ionic complex through triplet excimer of aromatic hydrocarbon or, when an electron acceptor is present, through triplet exciplex.The attack of cyanide ion on the transient complex yields the cyanated radical, ArHCN., which in aqueous acetonitrile reacts with itself to yield cyano- and dihydrocyano-products or, in dry acetonitrile after being attacked by an electron, is oxidized to the cyano-product.The rate constants for the formation of radical ions and the attack of cyanide ion are calculated from the experimental results.

Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones

The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported. The use of N-heterocyclic carbene as a ligand is essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones are applicable to this transformation, which gives aryl or alkenyl nitriles, respectively.

Cyanide-Free Cyanation of Aryl Iodides with Nitromethane by Using an Amphiphilic Polymer-Supported Palladium Catalyst

A cyanide-free aromatic cyanation was developed that uses nitromethane as a cyanide source in water with an amphiphilic polystyrene poly(ethylene glycol) resin-supported palladium catalyst and an alkyl halide (1-iodobutane). The cyanation proceeds through the palladium-catalyzed cross-coupling of an aryl halide with nitromethane, followed by transformation of the resultant (nitromethyl)arene intermediate into a nitrile by 1-iodobutane.

Molecular engineered palladium single atom catalysts with an M-C1N3subunit for Suzuki coupling

Single atom catalysis has emerged as a powerful technique for catalysis due to its outstanding performance and atom economy. Controlling the hybridization of the atom with its environment is crucial in determining the selectivity and/or yield of the reaction. However, the single atom environment is usually ill-defined and hard to predict because the pyrolysis process used in preparing SACs damages the original status of the precursors in the catalyst preparation. A molecular engineering approach to synthesize single atom catalysts (SACs) on a heterogeneous template provides a strategy to make SACs with a highly uniform coordinating environment. Herein, we report the preparation of a molecular engineered Pd single atom catalyst with a pre-defined M-N3C1 coordination (Pd-N3C1-SAC) using a structure-rigid Pd-N3C1 porphyrin as the precursor, which shows more efficient Suzuki coupling compared with the SAC with Pd-N4 coordination. The origin of the high activity of the Pd-N3C1-SAC is revealed through density functional theory calculations, where a lower reaction barrier for the rate-determining oxidative addition is identified. This journal is

Difluorocarbene-Based Cyanation of Aryl Iodides

A large number of efficient cyanation methods have been developed because of the wide range of applications of nitriles, but conventional methods usually suffer from the need for a toxic cyanation reagent. Although difluorocarbene chemistry has received increasing attention, the use of difluorocarbene as a sources of the nitrile carbon for nitrile groups remains largely unexplored. We describe a difluorocarbene-based cyanation of aryl iodides promoted by a cheap copper source, Cu(NO 3) 2 ·2.5H 2 O, under an air atmosphere. Ph 3 P + CF 2 CO 2-, an easily available and shelf-stable difluorocarbene reagent, and NaNH 2 are used as the carbon source and the nitrogen source for the nitrile group, respectively. The cyanation protocol is attractive because no toxic reagent is used and performing the reactions under an air atmosphere is operationally convenient.

Copper-catalyzed remote C–H arylation of polycyclic aromatic hydrocarbons (PAHs)

The regioselective C–H arylation of substituted polycyclic aromatic hydrocarbons (PAHs) is a desired but challenging task. A copper-catalyzed C7–H arylation of 1-naphthamides has been developed by using aryliodonium salts as arylating reagents. This protocol does not need to use precious metal catalysts and tolerates wide variety of functional groups. Under standard conditions, the remote C–H arylation of other PAHs including phenanthrene-9-carboxamide, pyrene-1-carboxamide and fluoranthene-3carboxamide has also accomplished, which provides an opportunity for the development of diverse organic optoelectronic materials.

Palladium-Catalyzed Cyanation of Aryl Halides Using Formamide and Cyanuric Chloride as a New “CN” Source

A new source of “CN” employing formamide and cyanuric chloride is introduced for the cyanation reactions. The treatment of formamide and 2,4,6-trichloro-1,3,5-triazine (TCT; cyanuric chloride) afforded an efficient cyanating agent which it can be used as a nontoxic, readily available, and non-expensive reagent in the cyanation transformations. In this study, palladium-catalyzed cyanation of aryl halides was successfully accomplished using this new “CN” source in high yields.

Immobilized palladium nanoparticles on a cyclodextrin-polyurethane nanosponge (Pd-CD-PU-NS): An efficient catalyst for cyanation reaction in aqueous media

Immobilized palladium nanoparticles on a cyclodextrin-polyurethane nanosponge (Pd-CD-PU-NS) were found to be an efficient heterogeneous catalyst in the cyanation reaction of aryl halides in aqueous media. This catalyst system is containing palladium nanoparticles with a size of ～7 nm. Moreover, the CD-PU-NS support formed microsphere-shaped structures with a size of ～100–200 nm. The TEM images show that Pd nanoparticles were formed in near spherical shape morphology and were immobilized in the structure of the CD-PU-NS support. Under our optimized reaction conditions, aryl cyanides were obtained in high yields in the presence of the Pd-CD-PU-NS catalyst. Our results demonstrated that the Pd-CD-PU-NS catalyst is highly effective in the cyanation reaction in aqueous media. Furthermore, the catalyst could be simply extracted from the reaction mixture, providing an efficient methodology for the synthesis of aryl cyanides. The Pd-CD-PU-NS catalyst could be recycled four times with almost consistent catalytic efficiency.

Electrochemical C-H cyanation of electron-rich (Hetero)arenes

A straightforward method for the electrochemical C-H cyanation of arenes and heteroarenes that proceeds at room temperature in MeOH, with NaCN as the reagent in a simple, open, undivided electrochemical cell is reported. The platinum electrodes are passivated by ad-sorbed cyanide, which allows conversion of an exceptionally broad range of electron-rich substrates all the way down to dialkyl arenes. The cyanide electrolyte can be replenished with HCN, opening opportunities for salt-free industrial C-H cyanation.