14271-83-1

Basic information

• Product Name: (4-METHOXY-PHENYL)-OXO-ACETONITRILE
• Synonyms: (4-METHOXY-PHENYL)-OXO-ACETONITRILE;4-METHOXYBENZOYL CYANIDE
• CAS NO: 14271-83-1
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• Mol File: 14271-83-1.mol

Chemical Properties

• Melting Point: 63-64 °C
• Boiling Point: 271.3±23.0 °C(Predicted)
• Appearance: /
• Density: 1.164±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (4-METHOXY-PHENYL)-OXO-ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-METHOXY-PHENYL)-OXO-ACETONITRILE(14271-83-1)
• EPA Substance Registry System: (4-METHOXY-PHENYL)-OXO-ACETONITRILE(14271-83-1)

Safety Data

• Hazardous Substances Data: 14271-83-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(4-METHOXY-PHENYL)-OXO-ACETONITRILE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new medications. Its chemical properties make it a valuable component in the creation of active pharmaceutical ingredients.
Used in Agrochemical Industry:
In the agrochemical sector, (4-METHOXY-PHENYL)-OXO-ACETONITRILE is used as a precursor in the production of certain agrochemicals, such as pesticides and herbicides, due to its reactivity and potential to form compounds with desired biological activities.
Used in Dyes Industry:
(4-METHOXY-PHENYL)-OXO-ACETONITRILE is utilized as a chemical intermediate in the synthesis of dyes, where its structural features contribute to the color and properties of the final dye products, enhancing their performance in various applications.

Upstream product

• 74-90-8 hydrogen cyanide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 1115-12-4 carbonyl cyanide 
• 100-66-3 methoxybenzene 
• 143-33-9 sodium cyanide 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 460-19-5 ethanedinitrile 
• 60083-35-4 3-(4-methoxy-phenyl)-3-oxo-2-phenylhydrazono-propionaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 104-47-2 p-methoxybenzylnitrile 
• 58327-36-9 α-Bromo-α-(4-methoxyphenyl)acetonitrile 
• 1052175-62-8 C₉H₈N₂O₄ 

Downstream Products

• 28191-29-9 2-(4-methoxyphenyl)-1,1,2-tricyanoethylene 
• 7465-88-5 4-methoxy-N-phenylbenzamide 
• 82791-83-1 (E)-2-(4-methoxybenzoyl)-3-phenylacrylonitrile 
• 155701-75-0 (Z)-3-cyano-1-(4-methoxyphenyl)-3-phenyl-2-propen-1-one 
• 16616-43-6 1-(4-methoxy-phenyl)-3-phenyl-propynone 
• 55275-61-1 2-amino-1-(4-methoxyphenyl)ethanol 
• 1400913-16-7 5-methyl-3-(4-methoxyphenyl)-7,8-dihydro-6Н-cyclopenta[e]pyrazolo[1,5-a]pyrimidine 
• 1400913-24-7 8-methyl-3-(4-methoxyphenyl)-6,7-dihydro-5Н-1,4,8а-triaza-s-indacene 
• 93439-79-3 3-amino-4-(4-methoxyphenyl)-1Н-pyrazole 
• 93439-79-3 5-amino-4-(4-methoxyphenyl)-1Н-pyrazole 
• 100-09-4 4-methoxybenzoic acid 
• 32766-61-3 4-methoxyphenylglyoxylate methyl ester 

Relevant articles and documents

Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction

Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.

Novel synthesis method of alpha-carbonyl acid ester

The invention discloses a novel synthesis method of alpha-carbonyl acid ester. The method comprises the following steps: carrying out chlorination reaction on an alpha-methylene-containing nitrile compound and chlorine to obtain dichloronitrile, reacting the dichloronitrile product in a sulfuric acid and water system to obtain formyl cyanide, then acquiring an imino sulfate compound in the same reaction system, and finally performing esterification to obtain the target product. The adopted reaction raw materials are wide in sources and low in price, highly toxic solid sodium cyanide can be prevented from being used in the prior art, the method is environmentally friendly, and the method is easy to operate, mild in condition and easy to industrialize.

Palladium-Catalyzed One-Pot Four-Component Synthesis of β-Cyano-α,β-unsaturated Ketones Using Calcium Carbide as an Acetylene Source and Potassium Hexacyanoferrate(II) as an Eco-Friendly Cyanide Source

Palladium-catalyzed one-pot four-component synthesis of β-cyano-α,β-unsaturated ketones by the reactions of aryl halides, calcium carbide, potassium hexacyanoferrate(II) and aroyl chlorides is described. The salient features of this protocol are the direct use of easy-to-handle acetylene source and eco-friendly cyanide source, wide scope of substrates with good functional group tolerance, and simple work-up procedure. (Figure presented.).

A Cyanide-Free Synthesis of Acylcyanides through Ru-Catalyzed C(sp3)-H-Oxidation of Benzylic Nitriles

A practical method for generation of acylcyanides devoid of any external cyanide sources is presented that relies on a mild Ru-catalyzed selective C?H-oxidation of benzylic nitriles. The starting materials are smoothly generated through condensation of the corresponding carboxylic acid amides using silanes. The obtained acylcyanides can be employed in a plethora of transformation as exemplified to some larger extend in the sequence of C?H-oxidation-Tischenko-rearrangement for the generation of structurally diverse benzoyloxycyanohydrines.

Acceptorless and Base-free Dehydrogenation of Cyanohydrin with (η6-Arene)halide(Bidentate Phosphine)ruthenium(II) Complex

Ruthenium-catalyzed dehydrogenation of cyanohydrins under acceptorless and base-free conditions was demonstrated for the first time in the synthesis of acyl cyanide. As opposed to the thermodynamically preferred elimination of hydrogen cyanide, the dehydrogenation of cyanohydrins could be kinetically controlled with ruthenium (II) bidentate phosphine complexes. The effects of the arene, phosphine ligands and counter anions were investigated in regard to catalytic activity and selectivity. Selective dehydrogenation can occur via β-hydride elimination with the experimentally observed [(alkoxide)Ru] complex. (Figure presented.).

Rh-Catalyzed Asymmetric Hydrogenation of 1,2-Dicyanoalkenes

A highly efficient enantioselective hydrogenation of 1,2-dicyanoalkenes catalyzed by the complex of rhodium and f-spiroPhos has been developed. A series of 1,2-dicyanoalkenes were successfully hydrogenated to the corresponding chiral 1,2-dicyanoalkanes under mild conditions with excellent enantioselectivities (up to 98% ee). This methodology provides efficient access to the asymmetric synthesis of chiral diamines.

Dual Lewis Acid/Lewis Base Catalyzed Acylcyanation of Aldehydes: A Mechanistic Study

A mechanistic investigation, which included a Hammett correlation analysis, evaluation of the effect of variation of catalyst composition, and low-temperature NMR spectroscopy studies, of the Lewis acid-Lewis base catalyzed addition of acetyl cyanide to prochiral aldehydes provides support for a reaction route that involves Lewis base activation of the acyl cyanide with formation of a potent acylating agent and cyanide ion. The cyanide ion adds to the carbonyl group of the Lewis acid activated aldehyde. O-Acylation by the acylated Lewis base to form the final cyanohydrin ester occurs prior to decomplexation from titanium. For less reactive aldehydes, the addition of cyanide is the rate-determining step, whereas, for more reactive, electron-deficient aldehydes, cyanide addition is rapid and reversible and is followed by rate-limiting acylation. The resting state of the catalyst lies outside the catalytic cycle and is believed to be a monomeric titanium complex with two alcoholate ligands, which only slowly converts into the product.

Synthesis of benzoyl cyanide through aerobic photooxidation of benzyl cyanide using carbon tetrabromide as a catalyst

We developed a synthetic method toward benzoyl cyanide through aerobic photooxidation of benzyl cyanide in the presence of carbon tetrabromide under visible light irradiation with fluorescent lamps.

A new convenient synthesis of aroyl cyanides via the formation of cyanohydrin nitrate intermediates

The treatment of α-bromoarylacetonitriles with AgNO3 generates cyanohydrin nitrate intermediates, which easily eliminate nitrous acid with the formation of carbonyl bond to afford aroyl cyanides in good to high yields.

Quantitative evaluation of the mechanism of electroreduction of benzoyl cyanides

The mechanism of reduction of benzoyl cyanide, 6, p-methoxybenzoyl cyanide, 7, and p-chlorobenzoyl cyanide, 8, has been studied in acetonitrile (6 and 7), N,N-dimethylformamide (6), and acetonitrile containing water (all three compounds). The reaction proceeds by initial reduction to form the anion radical followed by dimerization to produce an intermediate dianion, the dianion of the dicyanohydrin of benzil. The latter loses cyanide to give the anion of the monocyanohydrin of benzil, which undergoes two parallel reactions: expulsion of cyanide to give the corresponding benzil and rearrangement to the monoanion of mandelonitrile benzoate. The addition of water brings about an increase in the dimerization rate constant and an associated increase in the amount of benzil that is produced. The standard potentials for the initial reduction step have been evaluated, and their dependence on the substituent is discussed. The dimerization rate constants have also been evaluated.