874-90-8

Usage

Uses

Used in the Perfume Industry:
Anisonitrile is used as a raw material in the production of perfumes. Its aromatic properties contribute to the creation of various fragrances, enhancing the sensory experience of consumers.
Used in the Chemical Industry:
Anisonitrile is utilized as a chemical intermediate in the synthesis of various compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatility allows it to be a key component in the development of new and innovative products.
Used in the Flavor Industry:
Anisonitrile is also employed in the flavor industry to create unique taste profiles for food and beverage products. Its ability to impart distinct flavors makes it an essential ingredient in the formulation of various flavor compounds.

Synthesis Reference(s)

Journal of the American Chemical Society, 91, p. 4181, 1969 DOI: 10.1021/ja01043a028

InChI:InChI=1/C8H7NO/c1-10-8-4-2-7(6-9)3-5-8/h2-5H,1H3

Upstream product

• 123-91-1 1,4-dioxane 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 3717-22-4 (Z)-para-methoxybenzaldehyde oxime 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 110-86-1 pyridine 
• 16061-98-6 4-methoxybenzaldehyde oxime benzoyl ester 
• 628-13-7 pyridine hydrochloride 
• 1517-45-9 4-methoxy-benzaldehyde-((Z)-O-acetyl oxime ) 
• 684-78-6 O,N-bis-(trifluoroacetyl)-hydroxylamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 3717-21-3 (E)-4-methoxybenzaldoxime 
• 121-44-8 triethylamine 
• 2299-73-2 N,N-bis(4-methoxybenzylidene)hydrazine 

Downstream Products

• 659719-23-0 (6-hydroxy-3-methyl-benzofuran-2-yl)-(4-methoxy-phenyl)-ketone 
• 17061-62-0 N,N-bis(p-methoxybenzyl)amine 
• 63674-11-3 N-[(4-methoxyphenyl)methyl]cyclohexanamine 
• 59224-73-6 1-(4'-methoxylphenyl)-3,4-dihydroisoquinoline 
• 611-94-9 4-Methoxybenzophenone 
• 39739-49-6 methyl 4-methoxybenzimidate hydrochloride 
• 102810-68-4 4-isopropylidene-5-(4-methoxy-phenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrrole 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 33739-91-2 N-cyclohexyl-4-methoxybenzamide 
• 95317-74-1 6,7-dimethoxy-1-(4-methoxy-phenyl)-3-methyl-3,4-dihydro-isoquinoline 
• 121-97-1 4-Methoxypropiophenone 
• 6302-84-7 2-(4-methoxyphenyl)-4,5-dihydro-1H-imidazole 
• 123-11-5 4-methoxy-benzaldehyde 
• 4450-64-0 N₁-phenyl-4-methoxy-1-benzenecarboximidamide 

Relevant academic research and scientific papers

Structural studies of two isoelectronic tetrakis isocyano complexes

Two isoelectronic tetrakis isocyano compounds, tetra(p-isocyanoanisole) nickel(0) and tetra(p-isocyanoanisole)copper(I) hexafluorophosphate were synthesized from nickel bis cyclooctadiene and copper (I) tetra acetonitrile hexafluorophosphate and the isonitrile, respectively, and their structures were determined. The nickel complex crystallizes in the orthorhombic space group P212121 with a = 9.6709(8), b = 15.2324(13), c = 19.0955(16) A and Z = 4. The copper salt forms crystals with a tetragonal setting in P4/n with a = b = 15.8206(5), c = 6.5848(4) A and Z = 2. Both complexes exhibit the approximate tetrahedral coordination environment expected for 18 valence electron complexes with soft σ-donor π-acceptor ligands. Packing in the nickel complex is dominated by weak π-π stacking, C-H...;πphenyl, and C-H...;π interactions towards the isonitrile carbon and nitrogen atoms, and several slightly stronger C-H...;O interactions. In the copper complex the presence of the PF6 anion allows for the formation of stronger C-H...;F interactions, and these in combination with π-π stacking and C-H...;O hydrogen bonds dominate the packing.

Synthesis, coordination and catalytic use of phosphinoferrocene ligands bearing 6-phospha-2,4,6-trioxaadamantane P-donor moieties

1,1’-Bis(diphenylphosphino)ferrocene (dppf) and structurally related ferrocene bis-phosphines are indispensable ligands for coordination chemistry and catalysis. This contribution focuses on the coordination behaviour and catalytic properties of two dppf congeners bearing 1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane-8-yl groups (CgP) as the P-donor moieties, viz. Ph2PfcCgP (1) and its semi-homologous counterpart Ph2PfcCH2CgP (2; fc = ferrocene-1,1’-diyl). In reactions with a PdCl2 source, compound 1 produced exclusively the cis-chelate complex [PdCl2(1-κ2P,P’)], while the homologated ligand 2 afforded a complex mixture of compounds which equilibrated upon heating in methanol in favour of the symmetrical dimeric complex trans-[(μ-2)PdCl2]2 as a mixture of racemic and meso isomers. Notably, in aqueous Pd-catalysed cyanation of aryl bromides and Suzuki-Miyaura-type cross-coupling of benzoyl chlorides with boronic acids producing benzophenones, catalysts generated in situ from bis-phosphine 1 and Pd(II) sources were often more active than their counterparts resulting from dppf and 2.

Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors

This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound mask

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

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.

Construction of N-Acyliminophosphoranes via Iron(II)-Catalyzed Imidization of Phosphines with N-Acyloxyamides

Employing FeCl2as a cheap and readily available catalyst, a facile imidization of phosphines with N-acyloxyamides is described, affording synthetically useful N-acyliminophosphoranes with high functional group tolerance. The transformation is easily performed under an air atmosphere at room temperature and could be scaled up to gram scale with a catalyst loading of 1 mol %. The iminophosphoranyl moiety in the product was further utilized as an effective directing group for controllable ortho C(sp2)-H bond amidations under Rh(III) catalysis.

Nitrile Synthesis via Desulfonylative-Smiles Rearrangement

Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.

A highly stable all-in-one photocatalyst for aryl etherification: The NiIIembedded covalent organic framework

The efficient conversion of aryl bromides to the corresponding aryl alkyl ethers by dual nickel/photocatalysis has seen great progress, but difficulties of recycling the photosensitizer or nickel complexes cause problems of sustainability. Here, we report the design of a novel, highly stable vinyl bridge 2D covalent organic framework (COF) containing Ni, which combines the role of photosensitizer and reactive site. The as-prepared sp2c-COFdpy-Ni acts as an efficient heterogeneous photocatalyst for C-O cross coupling. The sp2c-COFdpy-Ni can be completely recovered and used repeatedly without loss of activity, overcoming the limitations of the prior methods. Preliminary studies reveal that strong interlayer electron transfer may facilitate the generation of the proposed intermediate sp2c-COFdpy-NiI in a bimolecular and self-sustained manner. This all-in-one heterogeneous photocatalyst exhibits good compatibility of substrates and tolerance of functional groups. The successful attempt to expand the 2D COFs with this new catalyst into photocatalytic organic transformation opens an avenue for photoredox/transition metal mediated coupling reactions.

Visible-Light Promoted C–O Bond Formation with an Integrated Carbon Nitride–Nickel Heterogeneous Photocatalyst

Ni-deposited mesoporous graphitic carbon nitride (Ni-mpg-CNx) is introduced as an inexpensive, robust, easily synthesizable and recyclable material that functions as an integrated dual photocatalytic system. This material overcomes the need of expensive photosensitizers, organic ligands and additives as well as limitations of catalyst deactivation in the existing photo/Ni dual catalytic cross-coupling reactions. The dual catalytic Ni-mpg-CNx is demonstrated for C–O coupling between aryl halides and aliphatic alcohols under mild condition. The reaction affords the ether product in good-to-excellent yields (60–92 %) with broad substrate scope, including heteroaryl and aryl halides bearing electron-withdrawing, -donating and neutral groups. The heterogeneous Ni-mpg-CNx can be easily recovered from the reaction mixture and reused over multiple cycles without loss of activity. The findings highlight exciting opportunities for dual catalysis promoted by a fully heterogeneous system.

SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution

A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.