19924-43-7

Basic information

• Product Name: (3-Methoxyphenyl)acetonitrile
• Synonyms: (3-Methoxyphenyl)ace;(3-METHOXYPHENYL)ACETONITRILE FOR SYNTHE;3-Methoxyphenylacetonitrile, 98%+;3-ANISONITRILE;3-CYANOANISOLE;AKOS B004087;M-ANISONITRILE;M-METHOXYBENZONITRILE
• CAS NO: 19924-43-7
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• EINECS: 243-428-5
• Product Categories: Aromatic Nitriles;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 19924-43-7.mol

Chemical Properties

• Melting Point: 8C
• Boiling Point: 164 °C
• Flash Point: 221 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.054 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00264mmHg at 25°C
• Refractive Index: n20/D 1.5402(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• Water Solubility: INSOLUBLE
• BRN: 1865539
• CAS DataBase Reference: (3-Methoxyphenyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (3-Methoxyphenyl)acetonitrile(19924-43-7)
• EPA Substance Registry System: (3-Methoxyphenyl)acetonitrile(19924-43-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 19924-43-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(3-Methoxyphenyl)acetonitrile is used as a synthetic intermediate for the production of isoflavones, which are known to inhibit epithelial cell proliferation and induce apoptosis in vitro. These properties make isoflavones potential candidates for the development of treatments for various diseases, including cancer.
Used in Chemical Research:
(3-Methoxyphenyl)acetonitrile is also used in the synthesis of new immunogens, such as homovanillic acid β,β′-cyclobisalkylated melatoninergic phenylalkylamides and α-sec-butyl-3-methoxy phenylacetonitrile. These compounds have potential applications in the development of new drugs and therapies.
Used as an Antispasmodic Agent:
(3-Methoxyphenyl)acetonitrile is used as an antispasmodic agent, which can help in the treatment of various conditions characterized by involuntary muscle contractions or spasms.

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

Upstream product

• 151-50-8 potassium cyanide 
• 824-98-6 m-methoxybenzyl chloride 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 143-33-9 sodium cyanide 
• 107-14-2 chloroacetonitrile 
• 100-66-3 methoxybenzene 
• 578-57-4 2-bromoanisole 
• 75-05-8 acetonitrile 
• 13435-20-6 tetraethylammoniumcyanide 
• 76979-31-2 (E,Z)-5-(3-methoxyphenylmethylene)-4-oxo-2-thioxothiazolidine 
• 773837-37-9 sodium cyanide 
• 10365-98-7 3-methoxyphenylboronic acid 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 2845-89-8 1-chloro-3-methoxy-benzene 

Downstream Products

• 104396-29-4 (3-methoxy-phenyl)-thiazol-2-yl-acetonitrile 
• 111474-27-2 2-(3-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone 
• 108774-68-1 (6,7-dimethoxy-cinnolin-4-yl)-(3-methoxy-phenyl)-acetonitrile 
• 35553-92-5 ETHYL 3-METHOXYPHENYLACETATE 
• 109254-16-2 1-benzyl-4-(3-methoxy-phenyl)-piperidine-4-carbonitrile 
• 103394-50-9 (3-methoxy-phenyl)-acetaldehyde-semicarbazone 
• 103275-92-9 3-methoxyphenyl-(2-pyridyl)acetonitrile 
• 65292-99-1 2-(3-methoxyphenyl)acetaldehyde 
• 109156-97-0 cinnolin-4-yl-(3-methoxy-phenyl)-acetonitrile 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 113114-02-6 1-[3-cyclohex-1-enyl-3-(3-methoxy-phenyl)-propyl]-piperidine 
• 61134-88-1 2-(3-methoxyphenyl)-N,N-dimethylethan-1-amine 
• 37786-58-6 3-cyano-1-(dimethylamino)-3-(m-methoxyphenyl)propane 
• 855365-59-2 3-(3-methoxy-phenyl)-pentane-1,3,5-tricarbonitrile 

Relevant articles and documents

Preparation method of m-methoxyphenethylamine

The invention discloses a preparation method of m-methoxyethylamine, and relates to the field of organic synthesis preparation chemistry. The preparation method comprises the following steps: adding M-methoxybenzyl chloride to an aqueous solution of cyanide, carrying out cyanation reaction at 60 - 95 °C DEG C, generating M-methoxycyanide, and then cooling and crystallizing in acetone to obtain m-methoxycyanide crystals. A proper amount of ammonia gas is introduced into the solvent, then a proper amount of ammonia gas is introduced, and then hydrogen is introduced to carry out catalytic hydrogenation reaction at a temperature 110 - 160 °C, and the hydrogenated product is distilled under reduced pressure to obtain m-methoxyethylamine. The preparation method of the meta-methoxyethylamine is simple, the raw materials are easily available, the process is easy to control, the cost is low, and the method has the characteristics of high yield, high purity, environmental friendliness and the like, and is suitable for industrial production.

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.

Crown ether functionalized magnetic hydroxyapatite as eco-friendly microvessel inorganic-organic hybrid nanocatalyst in nucleophilic substitution reactions: an approach to benzyl thiocyanate, cyanide, azide and acetate derivatives

In this paper, high catalytic activity of 4′,4″-diformyl dibenzo-18-crown-6 anchored onto the functionalized magnetite hydroxyapatite (γ-Fe2O3@HAp–Crown) as a new, versatile and magnetically recoverable catalyst, was prepared. It evaluated as phase-transfer catalyst and molecular host system for nucleophilic substitution reactions of benzyl halides with thiocyanate, cyanide, azide and acetate anions in water. No evidence for the formation of by-products was observed and the products obtained in pure form without further purification. The nanocomposite was easily removed from solution via application of a magnetic field, allowing straightforward recovery and reuse. The synthesized nanocomposite was characterized by several techniques such as FT-IR, TGA-DTG, EDX, XRD, BET, FE-SEM, TEM and VSM.

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.

Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.

Ionic liquid-induced conversion of methoxymethyl-protected alcohols into nitriles and iodides using [Hmim][NO3]

This Letter reports a one-pot efficient conversion of methoxymethyl-ethers into their corresponding nitriles and iodides using the ionic liquid, 1-methyl-3H-imidazolium nitrate ([Hmim][NO3]) under microwave irradiation. A variety of products were prepared in high yields using this method.

One-pot synthesis of nitriles from aldehydes catalyzed by deep eutectic solvent

The choline chloride-urea (1:2) based deep eutectic mixture as an efficient and ecofriendly catalyst for the one-pot synthesis of nitriles from aldehydes under solvent-free conditions under both conventional and microwave irradiation; the products were obtained in good to excellent yields. Georg Thieme Verlag Stuttgart New York.

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.

Magnetic nanoparticles grafted with β-cyclodextrin-polyurethane polymer as a novel nanomagnetic polymer brush catalyst for nucleophilic substitution reactions of benzyl halides in water

The polymer coated magnetic nanoparticles has gained significant attention for potential applications in biomedicine, separations, and magnetic storage. In this study, β-cyclodextrin-polyurethane polymer coated Fe 3O4 magnetic nanoparticle as a novel class of hybrid organic/inorganic molecular catalyst was successfully prepared and evaluated as solid-liquid phase-transfer catalyst and molecular host system for nucleophilic substitution reactions. The nanocomposite has demonstrated the ability to catalytic the nucleophilic substitution reaction of benzyl halides with thiocyanate, azide, cyanide and acetate anions in water. No evidence for the formation of by-products for example isothiocyanate or alcohol was observed and the products obtained in pure form without further purification. The nanomagnetic polymer brush catalyst was easily removed from solution via application of a magnetic field, allowing straightforward recovery and reuse. Results obtained from scanning electron microscopy (SEM) and vibrating sample magnetometery (VSM) show that the synthesized magnetic nanocomposite are superparamagnetic with a mean diameter of 59 nm. The grafting of β-cyclodextrin-polyurethane polymer to Fe3O4 magnetic nanoparticle is confirmed by Fourier transform infrared spectroscopy (FT-IR).

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.