7035-03-2

Basic information

• Product Name: 2-Methoxyphenylacetonitrile
• Synonyms: (o-Methoxyphenyl)acetonitrile;Benzeneacetonitrile, 2-methoxy-;o-Methoxyphenylacetonitrile;O-ANISYL CYANIDE;O-METHOXYBENZYL CYANIDE;2-METHOXYBENZYL CYANIDE;(2-METHOXYPHENYL)ACETONITRILE;2-Methoxyphenyl Acetonitrile 2-Methoxybenzyl Cyanide o-Methoxybenzyl Cyanide
• CAS NO: 7035-03-2
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• EINECS: 230-314-5
• Product Categories: Aromatic Nitriles
• Mol File: 7035-03-2.mol

Chemical Properties

• Melting Point: 65-67 °C(lit.)
• Boiling Point: 143 °C15 mm Hg(lit.)
• Flash Point: 129°C
• Appearance: white to slightly brown crystalline powder
• Density: 1.1135 (rough estimate)
• Vapor Pressure: 0.00767mmHg at 25°C
• Refractive Index: 1.5309 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 0.01g/l
• BRN: 2087748
• CAS DataBase Reference: 2-Methoxyphenylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxyphenylacetonitrile(7035-03-2)
• EPA Substance Registry System: 2-Methoxyphenylacetonitrile(7035-03-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36/37-36-26
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 7035-03-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxyphenylacetonitrile is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of a wide range of therapeutic agents with diverse biological activities. One specific application is in the synthesis of 2-(1-cyano-1-(2-methoxy)phenyl)methylidene-3-phenylthiazolidine-4,5-dione, which is a compound with potential pharmaceutical applications.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Methoxyphenylacetonitrile serves as a building block for the development of new pesticides and other crop protection agents. Its versatile structure enables the design of molecules with improved efficacy, selectivity, and reduced environmental impact.
Used in Specialty Chemicals:
2-Methoxyphenylacetonitrile is also utilized in the production of specialty chemicals, such as dyes, pigments, and additives for various industrial applications. Its unique chemical properties make it a valuable component in the development of innovative materials with enhanced performance characteristics.

InChI:InChI=1/C9H9NO/c1-11-9-5-3-2-4-8(9)6-7-10/h2-5H,6H2,1H3

Upstream product

• 52289-93-7 o-Methoxybenzyl bromide 
• 151-50-8 potassium cyanide 
• 408310-12-3 2-ethoxycarbonyl-2-hydroxy-2-(2-methoxylphenyl)-acetonitrile 
• 7035-02-1 o-Methoxybenzyl chloride 
• 107-14-2 chloroacetonitrile 
• 100-66-3 methoxybenzene 
• 557-21-1 zinc(II) cyanide 
• 578-57-4 2-bromoanisole 
• 105-56-6 ethyl 2-cyanoacetate 
• 766-51-8 2-Chloroanisole 
• 19350-70-0 2-methoxybenzaldehyde p-toluenesulfonylhydrazone 
• 333-20-0 potassium thioacyanate 
• 33567-59-8 (2-methoxy-phenyl)-acetaldehyde 
• 2045-79-6 o-methoxy-2-phenylethylamine 

Downstream Products

• 110394-05-3 1-(6-hydroxy-2,3-dihydro-benzofuran-5-yl)-2-(2-methoxy-phenyl)-ethanone 
• 16469-98-0 6-(2-methoxy-phenyl)-pteridine-2,4,7-triamine 
• 6056-23-1 ethyl (2-methoxyphenyl)acetate 
• 107100-95-8 (2-methoxy-phenyl)-((Ξ)-phthalidyliden)-acetonitrile 
• 88612-39-9 ethyl 2-cyano-2-(2-methoxyphenyl)acetate 
• 105190-07-6 (6-chloropyridazin-3-yl)-(2-methoxyphenyl)acetonitrile 
• 116377-27-6 2-cyano-3-(2'-methoxybenzyl)-1,5-dimethoxybenzene 
• 126256-22-2 4-Hydroxy-2-(2-methoxyphenyl)-4-methyl-3-phenyl-2-pentennitril 
• 126256-08-4 2-(2-Methoxyphenyl)-3,3-dimethyl-4-oxo-4-phenylbutyronitril 
• 30490-54-1 2-chloroacridine-10-carbonitrile 
• 77985-59-2 2-chloroacridine-10-carbonitrile N-oxide 
• 94100-12-6 5-chloro-3-(2-methoxyphenyl)-2,1-benzisoxazole 
• 116753-60-7 2-(2-methoxyphenyl)-3-methylbutyronitrile 
• 81616-80-0 (S)-2(2-methoxyphenyl)propionic acid 

Relevant articles and documents

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

Nickel-Catalyzed Deaminative Cyanation: Nitriles and One-Carbon Homologation from Alkyl Amines

A nickel-catalyzed deaminative cyanation of Katritzky pyridinium salts has been developed. When it is coupled with formation of the pyridinium salt from primary amines, this method enables alkyl amines to be converted to alkyl nitriles. A less toxic cyanide reagent, Zn(CN)2, is utilized, and diverse functional groups and heterocycles are tolerated. The method also enables a one-carbon homologation of alkyl amines via reduction of the nitrile products, in addition to many other potential transformations of the versatile nitrile group.

Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides

α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.

Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source

A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.

One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions

A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.

Oxidant-free conversion of primary amines to nitriles

An amide-derived NNN-Ru(II) hydride complex catalyzes oxidant-free, acceptorless, and chemoselective dehydrogenation of primary and secondary amines to the corresponding nitriles and imines with liberation of dihydrogen. The catalyst system tolerates oxidizable functionality and is selective for the dehydrogenation of primary amines (-CH2NH2) in the presence of amines without α-CH hydrogens.

A heterogeneous palladium catalyst hybridised with a titanium dioxide photocatalyst for direct C-C bond formation between an aromatic ring and acetonitrile

A palladium catalyst hybridised with a titanium dioxide photocatalyst can promote cyanomethylation of an aromatic ring by using acetonitrile, where the photocatalyst activates acetonitrile to form a cyanomethyl radical before the C-C bond formation using the palladium catalyst.

Antimicrobial volatile glucosinolate autolysis products from Hornungia petraea (L.) Rchb. (Brassicaceae)

Plant samples of Hornungia petraea were analyzed for glucosinolate (GLS) autolysis metabolites for the first time. GC-MS analysis of the autolysate and the synthesis of a series (12 compounds) of possible glucosinolate breakdown products revealed/corroborated the presence of glucoaubrietin, glucolimnanthin, glucolepigramin and glucotropaeolin in this species as the most likely "mustard oil" precursors. GLS degradation products identified in the autolysate of H. petraea, benzyl isothiocyanate, 3- and 4-methoxybenzyl isothiocyanate, along with several other structurally related compounds were evaluated for antimicrobial activity in order to possibly pinpoint the role of the latter secondary metabolites in the plant tissues. The assays showed a very high antibacterial activity of the tested isothiocyanates against Sarcina lutea and an antifungal effect against Aspergillus fumigatus and Candida albicans with MIC values in the order of 1 μg/ml value.

Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates

Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright

Synthesis of 7-cyano- and 7-acetamido-indoles via cyanocarbonation/hydrogenation of 7-formyl indole

A procedure for the synthesis of 7-cyano and 7-acetamido indoles via cyanocarbonation/hydrogenation of 7-formyl indole is presented. The process can be efficiently scaled up to provide multigram quantities of the desired compounds in good yield. A small survey of substrate scope indicates that the reaction may prove generally useful for the synthesis of aryl acetonitriles.