874-90-8

Basic information

• Product Name: Anisonitrile
• Synonyms: P-ANISIC ACID NITRILE;P-ANISONITRILE;P-METHOXYBENZONITRILE;4-CYANOANISOLE;4-ANISONITRILE;4-METHOXYBENZONITRILE;ANISONITRILE;1-Cyano-4-methoxybenzene
• CAS NO: 874-90-8
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.15
• EINECS: 212-871-6
• Product Categories: Benzene derivatives;Aromatic Nitriles;Nitrile;Nitriles;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds;Aromatics;Miscellaneous Reagents
• Mol File: 874-90-8.mol

Chemical Properties

• Melting Point: 57-59 °C(lit.)
• Boiling Point: 256-257 °C765 mm Hg(lit.)
• Flash Point: 256-257°C
• Appearance: White to slightly beige/Crystalline Powder
• Density: 1.1475 (rough estimate)
• Vapor Pressure: 0.0153mmHg at 25°C
• Refractive Index: 1.5402 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• Water Solubility: soluble
• Sensitive: Hygroscopic
• BRN: 508117
• CAS DataBase Reference: Anisonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Anisonitrile(874-90-8)
• EPA Substance Registry System: Anisonitrile(874-90-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-20/21/22-36/37/38
• Safety Statements: 36/37-36-26
• RIDADR: 3276
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 874-90-8(Hazardous Substances Data)

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

• 110-86-1 pyridine 
• 16061-98-6 4-methoxybenzaldehyde oxime benzoyl ester 
• 121-44-8 triethylamine 
• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 
• 112129-06-3 N-chloro-4-methoxybenzenemethanimine 
• 16061-98-6 anti-4-methoxyphenylmethanal-O-benzoyloxime 
• 1693-84-1 4-methoxy-benzaldehyde-((E)-O-acetyl oxime ) 
• 67-56-1 methanol 
• 5396-38-3 1-(tert-butyl)-4-methoxybenzene 
• 143-33-9 sodium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 696-62-8 para-iodoanisole 
• 557-21-1 dicyanozinc 

Downstream Products

• 611-94-9 4-Methoxybenzophenone 
• 6576-06-3 1-(4-methoxyphenyl)-2-(pyridin-4-yl)ethanone 
• 68204-87-5 furan-3-yl(4-methoxyphenyl)methanone 
• 5064-00-6 (4-methoxyphenyl)(thiophen-3-yl)methanone 
• 139962-75-7 2-(4-Methoxyphenyl)<1H>pyrrolo<2,3-b>quinoline 
• 100-09-4 4-methoxybenzoic acid 
• 203628-19-7 5-(dimethylamino)-3-(4-methoxyphenyl)isoquinolin-1(2H)-one 
• 221907-28-4 (Z)-2-(4,5-dihydro-1,3-oxazol-2-yl)-1-(4-methoxyphenyl)-1-propen-1-amine 
• 2362-64-3 p-methoxythiobenzamide 
• 17061-62-0 N,N-bis(p-methoxybenzyl)amine 
• 63674-11-3 N-[(4-methoxyphenyl)methyl]cyclohexanamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 2393-23-9 4-methoxy-benzylamine 
• 21160-26-9 2-methoxy-1-(4-methoxy-phenyl)-ethanone 

Relevant articles and documents

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

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 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.

A new reagent for efficient synthesis of nitriles from aldoximes using methoxymethyl bromide

This study outlines an efficient, high-yielding, and rapid method by which to access diverse nitriles from aldoximes with methoxymethyl bromide (MOM-Br) in THF. It represents the first application of MOM-Br as a deoximation reagent to synthesize nitriles. The reaction was performed at reflux to ensure excellent yield (79-96%) of the nitriles within 20-45 minutes. Furthermore, this method has been successfully applied to the synthesis of the synthesis precursor of aromatic, heteroaromatic, cyclic, and acyclic aliphatic.

Dehydration of aldoximes to nitriles using trichloroacetonitrile without catalyst

Trichloroacetonitrile has been found to be an efficient dehydrating agent for a range of aldoximes including aromatic and heterocyclic aldoxime yielding the corresponding nitriles in moderate to good yields. The dehydration reactions can take place in non-acetonitrile media without the aid of a metal catalyst. In addition, it has been confirmed that trichloroacetonitrile was converted into trichloroacetamide in the reaction.

Production method of anisonitrile

The invention belongs to the technical field of chemical engineering, and particularly relates to a production method of anisonitrile, which comprises: 1) carrying out an amidation reaction on p-hydroxybenzoic acid and carbamate under the action of a catalyst to generate p-hydroxybenzamide, 2) synthesizing p-methoxybenzamide from p-hydroxybenzamide in dimethyl carbonate under the action of the catalyst, and 3) dehydrating the p-methoxybenzamide in dimethyl carbonate in the presence of a dehydrating agent at 80-90 DEG C for 3-6 hours to obtain the anisonitrile. The purity of the anisonitrile product obtained by the production method is as high as 99.4%-99.8%, the yield of the anisonitrile product is as high as 98.0%-99.2%, the total yield of the reaction is as high as 95.7%-98.1% based on p-hydroxybenzoic acid, the yield is high, highly toxic substances are not used in the production process, no wastewater is generated, the used solvent is safe, environment-friendly and easy to recover,the raw materials are low in price, and large-scale production can be achieved.