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
• Article Data: 883

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

Description

Anisonitrile, also known as 4-methoxybenzonitrile, is a white to light yellow crystal powder that serves as a versatile chemical intermediate in various industries. Its unique chemical properties make it a valuable component in the synthesis of a range of products.

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

• 6305-18-6 2-(4-methoxybenzoyl)pyridine 
• 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 

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.

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.

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.