2980-92-9

Usage

Chemical class

Isonitriles (isocyanides)

Molecular structure

Phenyl group substituted with two ethyl groups and an isocyanide functional group

Odor

Strong, pungent

Uses

Organic synthesis, nucleophilic addition reactions, ligand in transition metal catalyzed processes, preparation of pharmaceuticals, agrochemicals, and fine chemicals

Safety

Harmful if inhaled or comes into contact with skin

InChI:InChI=1/C11H13N/c1-4-9-7-6-8-10(5-2)11(9)12-3/h6-8H,4-5H2,1-2H3

Upstream product

• 39086-39-0 N-(2,6-diethylphenyl)formamide 
• 579-66-8 2,6-diethylaniline 
• 119072-54-7 2,6-dimethylphenyl isonitrile 
• 74-88-4 methyl iodide 

Downstream Products

• 53042-91-4 2',6'-Diaethyl-N-thioformylbenzanilid 
• 53043-08-6 C₁₄H₂₂NOPS₂ 
• 53042-89-0 N-Thioformyl-2',6'-diaethylpropionanilid 
• 53042-92-5 2',6'-Diaethyl-N-thioformyl-2-chloroacetanilid 
• 53043-04-2 C₂₃H₂₄NPS₂ 
• 22747-77-9 Cyclohexen-1-ylglyoxylsaeure-1-(2,6-diethylanilid)-2-(2,6-diethylanil) 
• 53042-98-1 2,6-Diaethylthioformanilid 
• 53043-07-5 C₁₃H₂₀NO₂PS₂ 
• 53042-90-3 N-Thioformyl-2',6'-diaethylacetanilid 
• 176164-69-5 [Fe2(η(5)-C5H5)2(CO)(CNC6H3-2,6-Et2)(μ-CO)(μ-CNMe2)]I 
• 844857-76-7 trans-[Pd(CCPh)(N=C=N-C₆H₃-2,6-Et₂)(PMe₃)2] 
• 813434-28-5 [Pd(NCNC₆H₃-2,6-Et₂)(6-phenyl-2,2'-bipyridine^(1-))] 
• 1234675-07-0 2,6-diethyl-N-(9H-fluoren-9-ylidene)aniline 
• 1311202-63-7 C₂₇H₃₁NSi 

Relevant academic research and scientific papers

Access to Unsymmetrically Substituted Diaryl Gold N-Acyclic Carbene (NAC) and N-Heterocyclic Carbene (NHC) Complexes via the Isonitrile Route

A variety of unsymmetric diaryl gold N-acyclic carbene (NAC) complexes was synthesized via the isonitrile route by three different methods: (a) solvent free in a melt, (b) mechanochemically and (c) in THF at room temperature. The latter method can also be used to synthesize unsaturated gold NHC complexes. These methods overall offer access to a broad array of new complexes and remove one of the previous limitations of the isonitrile route to NAC and NHC complexes of gold, namely the inability to react with the less nucleophilic aromatic amines. The new complexes also proved to be successful as pre-catalysts in the gold-catalyzed phenol synthesis. (Figure presented.).

Palladium-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)-H activation: Concise synthesis of indole derivatives

Synthesis of the indole skeleton was achieved using a Pd-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)-H activation. It was found that slow addition of isocyanide is effective for reducing the amount of catalyst needed and Ad2PnBu is a good ligand for C(sp3)-H activation. The construction of the tetracyclic carbazole skeleton was also achieved by a Pd-catalyzed domino reaction incorporating alkyne insertion.

A short way to switchable carbenes

A new, one-step route to N-heterocyclic oxo-carbene complexes (NHOCs), representatives of chemo-switchable NHC complexes, is reported. This simple procedure provides an easy access to gold, palladium and platinum complexes of these ligands. Copyright

INDOLE SYNTHESES UTILIZING o-METHYLPHENYL ISOCYANIDES.

New indole synthesis starting with o-methylphenyl isocyanides such as o-tolyl, 2,4-xylyl, and 2,6-xylyl isocyanide is described. Treatment of o-tolyl isocyanide with LDA in diglyme at minus 78 degree C generated selectively o-(lithiomethyl)phenyl isocyanide in an almost quantitative yield, which on warming up to room temperature was cyclized to indole after aqueous workup. Similarly, 2,4-xylyl and 2,6-xylyl and 2,6-xylyl isocyanides were cyclized to 5-methylindole and 7-methylindole quantitatively. The o-(lithiomethyl)phenyl isocyanides reacted with electrophiles such as alkyl halides and alkylene oxides to give o-alkylphenyl isocyanides, which were cyclized via the lithiation at the orthobenzylic carbon to afford 3-substituted indoles.

Isonitriles as herbicide extenders

Herbicidally active thiolcarbamates are employed in combination with certain substituted phenyl isonitriles having the formula STR1 in which R1 is selected from the group consisting of C1 -C6 alkyl, C1 -C6 alkoxy, C1 -C6 alkylthio, phenyl, halogen, benzylthio, and p-chlorobenzylthio, and R2 is selected from the group consisting of hydrogen, C1 -C6 alkyl, C1 -C6 alkoxy, and halogen. In a typical application, the isonitrile is included in sufficient quantity to lessen the rate of soil degradation of the thiolcarbamate. As a result, the herbicidal effectiveness of the thiolcarbamate is enhanced and prolonged, rendering a single application of the herbicide effective over a longer period of time.