5955-74-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Methylbenzoyl cyanide is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs and medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Methylbenzoyl cyanide is utilized as an intermediate in the production of various agrochemicals, aiding in the creation of substances that protect crops and enhance agricultural productivity.
Used in Dye Production:
3-Methylbenzoyl cyanide is employed as a chemical intermediate in the manufacturing process of dyes, contributing to the coloration and stability of these products.
Used in Perfumery:
3-METHYLBENZOYL CYANIDE is also used in the perfume industry, where it plays a role in the creation of fragrances, enhancing their scent profiles and longevity.
Used in Other Industrial Applications:
Beyond the aforementioned uses, 3-Methylbenzoyl cyanide finds application in a variety of other industrial processes, where its chemical properties are leveraged to achieve specific outcomes in product development.

Upstream product

• 544-92-3 copper(I) cyanide 
• 1711-06-4 3-Methylbenzoyl chloride 
• 7677-24-9 trimethylsilyl cyanide 
• 151-50-8 potassium cyanide 
• 90775-12-5 2-bromo-2-(m-tolyl)acetonitrile 
• 2947-60-6 3-methylbenzyl cyanide 
• 393-52-2 2-Fluorobenzoyl chloride 
• 57-12-5 cyanide^(1-) 
• 36718-84-0 4-nitrophenyl 3-methylbenzoate 
• 36106-78-2 2,4-dinitrophenyl 3-methylbenzoate 

Downstream Products

• 75599-78-9 3-Methyl-benzoic acid cyano-m-tolyl-methyl ester 
• 97590-55-1 (R)-2-Amino-1-m-tolyl-ethanol 
• 22899-60-1 3-amino-4-(m-tolyl)-1,2,5-oxadiazole 
• 1255526-37-4 C₁₆H₁₃NO₂ 
• 1255526-45-4 C₁₇H₁₅NO₃ 
• 32816-69-6 2‐oxo‐3‐(phenylamino)indoline‐3‐carbonitrile 
• 16537-19-2 tert-butyl m-methylbenzoate 

Relevant academic research and scientific papers

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.

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.

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.).

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.

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.

Structure-reactivity correlations in nucleophilic substitution reactions of Y-substituted phenyl X-substituted benzoates with anionic and neutral nucleophiles

A kinetic study is reported for the reactions of 4-nitrophenyl X-substituted benzoates (1a-l) and Y-substituted phenyl benzoates (2a-l) with two anionic nucleophiles (OH- and CN-) and three amines (piperidine, hydrazine, and glycylglycine) in 80 mol% H2O-20 mol% dimethyl sulfoxide (DMSO) at 25.0 ± 0.1 °C. Each Hammett plot exhibits two intersecting straight lines for the reactions of 1a-l with the anionic nucleophiles and piperidine, while the Yukawa-Tsuno plots for the same reactions are linear. The Hammett plots for the reactions of 2a-l with hydrazine and glycylglycine demonstrate much better linear correlations with σ- constants than with σ° or σ constants, indicating that the leaving group departure occurs at the rate determining step (RDS). On the contrary, σ- constants result in poorer Hammett correlation than σ° constants for the corresponding reactions with OH- and CN-, indicating that the leaving group departure occurs after the RDS for the reactions with the anionic nucleophiles. The large ρX value (1.7 ± 0.1) obtained for the reactions of 1a-l with the anionic nucleophiles supports the proposal that the reactions proceed through an addition intermediate with its formation being the RDS. The Royal Society of Chemistry 2006.

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.

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.

Reinterpretation of curved hammett plots in reaction of nucleophiles with aryl benzoates: Change in rate-determining step or mechanism versus ground-state stabilization

A kinetic study is reported for the reaction of the anionic nucleophiles OH-, CN-, and N3- with aryl benzoates containing substituents on the benzoyl as well as the aryloxy moiety, in 80 mol % H2O-20 mol % dimethyl sulfoxide at 25.0 °C. Hammett log k vs σ plots for these systems are consistently nonlinear. However, a possible traditional explanation in terms of a mechanism involving a tetrahedral intermediate with curvature resulting from a change in rate-determining step is considered but rejected. The proposed explanation involves ground-state stabilization through resonance interaction between the benzoyl substituent and the electrophilic carbonyl center in the two-stage mechanism. Accordingly, the data are nicely accommodated on the basis of the Yukawa-Tsuno equation, which gives linear plots for all three nuceophiles. Literature reports of the mechanism of acyl transfer processes are reconsidered in this light.

Oxime amides and hydrazone amides having fungicidal activity

The invention relates to compounds having usefulness in the control of Take-All disease in plants, particularly cereals, a method for the control of Take-All disease, and fungicidal compositions for carrying out the method. Compounds of the invention are oximes or hydrazones of arylgloxamides or heteroarylglyoxamides or cycloalkenylglyoxamides.