13014-48-7

Usage

Uses

Used in Pharmaceutical Industry:
(4-CHLORO-PHENYL)-OXO-ACETONITRILE is used as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new medications due to its reactive functional groups and structural properties.
Used in Agrochemical Industry:
In the agrochemical sector, (4-CHLORO-PHENYL)-OXO-ACETONITRILE serves as a key intermediate, playing a crucial role in the production of pesticides and other agrochemicals to enhance crop protection and yield.
Used in Organic Synthesis:
(4-CHLORO-PHENYL)-OXO-ACETONITRILE is utilized as a building block in the synthesis of complex organic molecules, showcasing its importance in creating a wide array of chemical compounds for diverse applications.

Upstream product

• 4236-13-9 p-chloro-2-(hydroxyimino)-2-phenylacetonitrile 
• 21994-57-0 (4-chloro-phenyl)-(4-dimethylamino-phenylimino)-acetonitrile 
• 1115-12-4 carbonyl cyanide 
• 108-90-7 chlorobenzene 
• 1904-60-5 3-amino-2-phenylquinazolin-4(3H)-one 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 13312-83-9 4-chloromandelonitrile 
• 66985-46-4 (+/-)-2-(4-chlorophenyl)-2-(trimethylsiloxy)-acetonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 122-01-0 4-chloro-benzoyl chloride 
• 151-50-8 potassium cyanide 
• 4998-15-6 4-chlorophenylglyoxal 
• 74772-59-1 2-benzyl-3-amino-4-oxo-3,4-dihydroquinazoline 
• 60-29-7 diethyl ether 

Downstream Products

• 41870-82-0 2-amino-1-(4-chlorophenyl)ethanol 
• 34966-48-8 ethyl 2-(4-chlorophenyl)-2-oxoacetate 
• 46290-15-7 p-chlorobenzoylmalononitrile 
• 68019-82-9 5-(4-chloro-phenyl)-2-methoxy-3-methyl-2,4-dioxo-2λ⁵-[1,3,2]oxazaphospholidine-5-carbonitrile 
• 6578-47-8 N-(α-Cyan-4-chlor-benzyliden)-N'-diaminomethylen-hydrazin 
• 6965-39-5 2-(4-chlorophenyl)-N'-hydroxyacetimidamide 
• 6833-15-4 4-chlorobenzanilide 
• 68019-83-0 5-(4-chloro-phenyl)-2-ethoxy-3-ethyl-2,4-dioxo-2λ⁵-[1,3,2]oxazaphospholidine-5-carbonitrile 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 623-03-0 4-Cyanochlorobenzene 
• 7099-88-9 4-chlorophenylglyoxylic acid 
• 54029-00-4 2-Oxo-2-(4-chlorophenyl)thioacetamide 
• 21741-98-0 3-amino-4-(p-chlorophenyl)-1,2,5-oxadiazole 
• 121019-59-8 4-amino-5-p-chlorophenyl-2-p-nitrophenyloxazole 

Relevant academic research and scientific papers

Reactions of Zirconocene-1-Aza-1,3-diene Complexes with Acyl Cyanides: Substrate-Dependent Synthesis of Acyl- or Non-Acyl-Substituted Pyrroles

Insertion of acyl cyanides into azazirconacyclopentenes derived from 1,3-azadienes has been described, which affords acyl- or non-acyl-substituted pyrroles upon acidic quenching. These reactions are initialized through C=O insertion into the azazirconacycle to afford seven-membered oxaazazirconacycles. In the cases of 1,4- or 1,2,4-substituted azadienes, addition of a second molecule of acyl cyanide followed by cyclization upon acidic quenching leads to acyl-substituted pyrroles. In the cases of 1,3,4-substituted azadienes, the addition of a second molecule of acyl cyanide cannot proceed due to the steric hindrance caused by the R3 group on the zirconium intermediate. Acidic quenching of the resulting zirconium intermediate affords non-acyl-substituted pyrroles.

Reaction of Aromatic Acyl Chlorides with Potassium or Sodium Cyanide Impregnated onto Amberlite XAD Resins. Efficient Synthesis of Aromatic Acyl Cyanides

The effects of alkali metal cyanide impregnated on Amberlite XAD resins (KCN/XAD, NaCN/XAD) have been examined using the cyanation of benzoyl chloride.In benzene, benzoyl cyanide was obtained in a very high yield with high selectivity under mild conditions.It is proposed that the reaction occurs on the surface of the resin.On the basis of the result obtained in the absence of any solvent, the reactivity of KCN/XAD toward dimerization of benzoyl cyanide has been found to be much poorer than that of KCN in solution.Although the reaction of acyl chlorides with KCN/XADor NaCN/XAD in benzene gave various acyl cyanides in good to excellent yields, no aliphatic acyl cyanide could be obtained.

A novel heterogeneous synthesis of acyl cyanides catalyzed by PEG400 and zinc iodide

Aroyl cyanides were readily synthesized in moderate yields by the cyanation of aroyl chlorides with dry powdered potassium cyanide under the catalysis of PEG400 and zinc iodide in dichloromethane at room temperature. A preliminary study on the one-pot preparation of acetyl cyanide was also reported.

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.

AgI-PEG400-KI catalyzed environmentally benign synthesis of aroyl cyanides using potassium hexacyanoferrate(II) as the cyanating agent

A practical cyanation of aroyl chlorides with 0.2 equivalent of non-toxic cyanide source, K4[Fe(CN)6], 3 mol% AgI, 4 mol% PEG-400, and 3 mol% KI as the catalyst system is described. The reactions were performed in DMF at room temperature and provided the corresponding aroyl cyanides in 64-89% yield, typically in less than ten hours. Georg Thieme Verlag Stuttgart.

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.

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.).

Preparation method for D, L-phenylglycine and analogue thereof

The invention provides a preparation method for D, L-phenylglycine and an analogue thereof. According to the method, benzaldehyde, an analogue thereof and hydrocyanic acid are adopted as raw materials and subjected to cyanidation reaction, and then 2-hydroxy-benzyl cyanide or 2-hydroxy-benzyl cyanide analogue (cyanohydrin for short) is generated. Cyanohydrin reacts with carbon dioxide and the aqueous solution of ammonia, and then 5-phenyl-hydantoin and an analogue thereof (hydantoin for short) are generated. hydantoin is successively subjected to steam stripping, alkaline hydrolysis, steam stripping, decolorization, neutralization, crystallization, washing, centrifuging, drying and the like to obtain D, L-phenylglycine and the analogue thereof. Compared with the prior art, the preparation method for D, L-phenylglycine and the analogue thereof can significantly and effectively reduce the pollution, and fewer inorganic salt by-products are generated. Meanwhile, the prepared D, L-phenylglycine and the analogue thereof are high in product yield and high in purity. Counted in benzaldehyde and the analogue thereof, the yield of D, L-phenylglycine and the analogue thereof is larger than or equal to 96%, and the product purity is larger than or equal to 99%. Meanwhile, the process flow is simple and feasible, so that the method is worthy of market popularization and application.

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.