620-22-4

Usage

Uses

Used in Chemical Synthesis Industry:
m-Tolunitrile is used as a chemical intermediate for the synthesis of various organic compounds, including pharmaceuticals, dyes, and agrochemicals. Its reactivity and functional groups allow for the formation of a wide range of products.
Used in Pharmaceutical Industry:
m-Tolunitrile is used as a building block in the development of pharmaceutical drugs. Its unique structure and properties enable the creation of new drug candidates with potential therapeutic applications.
Used in Dye Industry:
m-Tolunitrile is used as a precursor in the production of dyes. Its chemical properties allow for the synthesis of dyes with specific color characteristics and properties, making it valuable in the dye industry.
Used in Agrochemical Industry:
m-Tolunitrile is used as a starting material for the synthesis of agrochemicals, such as pesticides and herbicides. Its unique chemical structure contributes to the development of effective and targeted agrochemical products.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Nitriles, such as m-Tolunitrile, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Health Hazard

ACUTE/CHRONIC HAZARDS: m-Tolunitrile causes skin irritation on contact.

Fire Hazard

m-Tolunitrile is combustible.

Purification Methods

Dry the nitrile with MgSO4, fractionally distil it, then wash it with aqueous acid to remove possible traces of amines, dry and redistil it. [Beilstein 9 H 477, 9 I 191, 9 II 325, 9 III 2324, 9 IV 1717.]

InChI:InChI=1/C8H7N/c1-7-3-2-4-8(5-7)6-9/h2-5H,1H3

Upstream product

• 620-51-9 N,N'-di(3-methylphenyl)thiourea 
• 3085-53-8 N-formyl-m-toluidine 
• 110-05-4 di-tert-butyl peroxide 
• 100-47-0 benzonitrile 
• 2362-63-2 3-methylthiobenzamide 
• 104-85-8 para-methylbenzonitrile 
• 108-38-3 m-xylene 
• 108-44-1 1-amino-3-methylbenzene 
• 28987-79-3 m-tolylmagnesium bromide 
• 506-77-4 cyanogen chloride 
• 621-30-7 3-methylphenyl isothiocyanate 
• 618-47-3 m-toluamide 
• 529-19-1 2-Methylbenzonitrile 
• 108-41-8 1-chloro-3-methylbenzene 

Downstream Products

• 59190-58-8 [3]pyridyl-m-tolyl ketone 
• 55329-66-3 N-(m-methylbenzyl)acetamide 
• 99-36-5 1-methoxycarbonyl-3-methylbenzene 
• 22682-29-7 dimethyl-2,3' benzophenone 
• 858841-30-2 N-{thio-m-toluoy} m-tolamidine 
• 464-72-2 tetraphenylethane-1,2-diol 
• 109866-72-0 4-isopropylidene-2,2-dimethyl-5-m-tolyl-3,4-dihydro-2H-pyrrole 
• 120-33-2 ethyl 3-methylbenzoate 
• 51772-30-6 3'-Methylpropiophenone 
• 57494-02-7 1-(3-methylphenyl)-2-methyl-1-propanimine 
• 13152-95-9 2,3',4-trimethyldiphenylmethanone 
• 643-65-2 3-methyl benzophenone 
• 33497-37-9 3-methyl-α-phenylbenzenemethanimine 
• 29366-76-5 6-(3-methylphenyl)-2,4-diamino-1,3,5-triazine 

Relevant academic research and scientific papers

Eco-friendly synthesis of m-tolunitrile by heterogeneously catalysed liquid phase ammoxidation

The ammoxidation of m-xylene to m-tolunitrile over silica-supported Co-Mn-Ni catalyst was conducted for the first time in liquid phase without solvent in one-step procedure. Copyright

Thermally stable imidazole/heteropoly acid composite as a heterogeneous catalyst for m-xylene ammoxidation

Ammoxidation of m-xylene is evaluated in the presence of a customized heteropoly acid catalyst as an imidazole/molybdovanadophosphoric acid (imidazole/PMoV). Imidazole is employed to maintain its heterogeneous phase during the ammoxidation reaction and to provide the thermal stability of PMoV with the expectation that imidazole can generate strong electronic interactions with terminal molybdenum-oxygen on PMoV. The characterizations of the prepared catalysts are performed using SEM–EDX, XRD, FT-IR, Raman, XPS, and TGA to prove the physical and chemical changes by incorporating imidazole to PMoV, respectively. Also, the thermal stability of the developed catalyst is confirmed by the means of heat treatment test at relatively high temperature. The composite catalyst, imidazole/PMoV, shows an excellent conversion rate of over 98% with high selectivity of isophthalonitrile in m-xylene ammoxidation. Moreover, while the imidazole-free PMoV catalyst is deactivated and washed out during the reaction, the catalyst durability of the imidazole/PMoV is preserved without significant activity loss after 5 reaction cycles at 380 °C.

Synthesis method of m (p)-site alkyl substituted cyanobenzene

The invention relates to a synthesis method of m (p)-alkyl substituted benzonitrile, which comprises the following steps: (1) m (p)-alkyl substituted benzoate is mixed with ammonia gas after passing through a vaporization furnace, the mixture enters a reactor filled with a catalyst to react, and a gas phase at an outlet of the reactor is introduced into a receiving tank with cooling water to obtain a reaction liquid; and (2) layering the reaction liquid in the step (1) to obtain an oil phase which is an m (p)-alkyl substituted cyanobenzene crude product, and rectifying to obtain an m (p)-alkyl substituted cyanobenzene finished product. According to the synthetic method disclosed by the invention, the m (p)-alkyl substituted cyanobenzene can be prepared only by a one-step method, the reaction only needs to be carried out in a tubular reactor filled with a catalyst, the process route is short, the production efficiency is high, the yield is high, the purity is good, the method is safe, economical and environment-friendly, and the obtained product is high in yield and purity.

Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors

This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound mask

Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide

Pd(OAc)2/XPhos–SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly efficient catalyst for the cyanation of aryl chlorides with potassium ferrocyanide. The reaction proceeded smoothly at 100 or 120?oC with K2CO3 or KOAc as base, delivering a variety of aromatic nitriles in good to excellent yields. The isolation of the crude products is facilely performed by extraction with cyclohexane and more importantly, both expensive Pd(OAc)2 and XPhos–SO3Na in PEG-400/H2O system could be easily recycled and reused at least six times without any apparent loss of catalytic efficiency. Graphical Abstract: Palladium-catalyzed cyanation of aryl chlorides with potassium ferrocyanide leading to aryl nitriles by using Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O as a highly efficient and recyclable catalytic system is described.[Figure not available: see fulltext.]

METHOD FOR PRODUCING AROMATIC NITRILE COMPOUND AND CATALYST FOR SYNTHESIS OF AROMATIC NITRILE COMPOUND

PROBLEM TO BE SOLVED: To efficiently produce an aromatic nitrile compound by oxidizing a methyl group directly bonded to an aromatic ring into a cyano group by ammoxidation. SOLUTION: The present invention relates to a method for producing an aromatic nitrile compound wherein a zeolite carrying at least one selected from the group consisting of an alkali metal and an alkaline earth metal is used to, in the presence of ammonia, oxidize an aromatic compound having a methyl group bound to a carbon atom of an aromatic ring with oxygen. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2021,JPOandINPIT

Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes

This article describes a sequential Ir/Cu-mediated process for the meta-selective C-H radiofluorination of (hetero)arene substrates. In the first step, Ir-catalyzed C(sp2)-H borylation affords (hetero)aryl pinacolboronate (BPin) esters. The intermediate organoboronates are then directly subjected to copper-mediated radiofluorination with [18F]tetrabutylammonium fluoride to afford fluorine-18 labeled (hetero)arenes in high radiochemical yield and radiochemical purity. This entire process is performed on a benchtop without Schlenk or glovebox techniques and circumvents the need to isolate (hetero)aryl boronate esters. The reaction was automated on a TracerLab FXFN module with 1,3-dimethoxybenzene and a meta-tyrosine derivative. The products, [18F]1-fluoro-3,5-dimethoxybenzene and an 18F-labeled meta-tyrosine derivative, were obtained in 37 ± 5% isolated radiochemical yield and >99% radiochemical purity and 25% isolated radiochemical yield and 99% radiochemical purity, and 0.52 Ci/μmol (19.24 GBq/μmol) molar activity (Am), respectively.

Copper-promoted cyanation of aryl iodides with N,N-dimethyl aminomalononitrile

A copper-promoted cyanation of aryl iodides has been successfully developed by using N,N-dimethyl aminomalononitrile as the cyanide source with moderate toxicity and better stability. This reaction features broad substrate scope, excellent reaction yields, readily available catalyst, and simple reaction conditions.

Pd@CeO2-catalyzed cyanation of aryl iodides with K4Fe(CN)6·3H2O under visible light irradiation

Cyanation of aryl iodides is still challenging work for chemical researchers because of harsh reaction conditions and toxic cyanide sources. Herein, we have developed a new protocol based on the combination of the catalyst Pd@CeO2, nontoxic cyanide source K4[Fe (CN)6]·3H2O, and driving force visible light irradiation. The reaction is operated at relatively moderate temperature (55°C) and exhibits good catalytic efficiency of product aryl nitriles (yields of 89.4%). Moreover, the catalyst Pd@CeO2 possesses good reusability with a slight loss of photocatalytic activity after five consecutive runs. The reaction system based on the above combination shows a wide range of functional group tolerance under the same conditions. Reaction conditions such as temperature, time, the component of catalyst, and solutions are optimized by studying cyanation of 1-iodo-4-nitrobenzene as model reaction. According to these results, the possible mechanism of Pd@CeO2-catalyzed cyanation of aryl iodides under visible light irradiation is proposed based on the influence of visible light on the catalyst and reactant compounds. In all, we provided an environmental and economic method for preparation of aryl nitriles from cyanation of aryl iodides based on the goal of green chemistry for sustainable development.

Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst

A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.