22364-68-7

Basic information

• Product Name: 2-Methylbenzyl cyanide
• Synonyms: 2-methyl-benzeneacetonitril;2-Methylbenzeneacetonitrile;2-Tolylacetonitrile;Acetonitrile, o-tolyl-;Benzeneacetonitrile, 2-methyl-;-Methylbenzylcyanide;-Methylphenylacetonitrile;o-tolyl-acetonitril
• CAS NO: 22364-68-7
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17
• EINECS: 244-937-5
• Product Categories: Aromatic Nitriles
• Mol File: 22364-68-7.mol

Chemical Properties

• Melting Point: 142-143 °C
• Boiling Point: 244-250 °C
• Flash Point: >110°C
• Appearance: clear colorless to orange-reddish liquid
• Density: 1.056 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.52E-10mmHg at 25°C
• Refractive Index: 1.5264-1.5284
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Slightly soluble in water. Soluble in benzene, ethyl ether, ethanol.
• BRN: 907182
• CAS DataBase Reference: 2-Methylbenzyl cyanide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylbenzyl cyanide(22364-68-7)
• EPA Substance Registry System: 2-Methylbenzyl cyanide(22364-68-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-37/39-27-26
• RIDADR: 3439
• RTECS: AM2290000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 22364-68-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Methylbenzyl cyanide is used as an important raw material and intermediate in the field of organic synthesis. Its unique chemical structure allows for the creation of a diverse range of compounds, making it a valuable asset in this industry.
Used in Pharmaceuticals:
In the pharmaceutical industry, 2-Methylbenzyl cyanide serves as a crucial intermediate for the development of various drugs. Its versatile chemical properties enable the synthesis of new and innovative medications, contributing to the advancement of healthcare.
Used in Agrochemicals:
2-Methylbenzyl cyanide is also utilized as a key intermediate in the agrochemical sector. It plays a vital role in the production of pesticides, herbicides, and other agricultural chemicals, helping to improve crop yields and protect plants from harmful pests.
Used in Dyestuff:
The dyestuff industry benefits from the use of 2-Methylbenzyl cyanide as an essential intermediate. Its incorporation in the manufacturing process leads to the development of a wide array of dyes with different colors and properties, catering to the diverse needs of various industries.

InChI:InChI=1/C7H12Cl2N2O2/c8-4-6(12)10-2-1-3-11-7(13)5-9/h1-5H2,(H,10,12)(H,11,13)

Upstream product

• 151-50-8 potassium cyanide 
• 89-92-9 2-methylbenzyl bromide 
• 143-33-9 sodium cyanide 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 95-46-5 2-methylphenyl bromide 
• 17729-59-8 tri-n-butyl(cyanomethyl)stannane 
• 107-14-2 chloroacetonitrile 
• 108-88-3 toluene 
• 84109-17-1 2-methylphenylzinc chloride 
• 590-17-0 cyanomethyl bromide 
• 183657-67-2 C₂₂H₁₈N₂O₄ 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 95-47-6 o-xylene 
• 76024-92-5 1-Methyl-2-(2-nitro-ethyl)-benzene 

Downstream Products

• 5466-19-3 2-o-tolyl-pyrido[2,3-b]pyrazine-3,6-diyldiamine 
• 31881-09-1 3c-(2-chloro-phenyl)-2-o-tolyl-acrylonitrile 
• 87968-36-3 α-cyano-2-methylstilbene 
• 412282-12-3 3-cyano-2-oxo-3-o-tolyl-propionic acid ethyl ester 
• 854884-65-4 1-o-tolyl-cyclopent-3-enecarbonitrile 
• 850856-04-1 3-methyl-4-phenyl-2-o-tolyl-butyronitrile 
• 38362-89-9 1-methyl-2-(2-nitroethyl)benzene 
• 40089-14-3 o-methylphenylacetamide 
• 644-36-0 o-methylphenylacetic acid 
• 55755-16-3 2-methylphenethylamine 
• 58422-60-9 2-(2-methylphenyl)propanenitrile 
• 1136-24-9 α-o-tolyl α-cyanoacetate 
• 107960-33-8 2-methyl-α-hydroxyiminobenzeneacetonitrile 
• 105902-47-4 2-(2-methylphenyl)-3-methylbutyronitrile 

Relevant articles and documents

Influence of Functional Groups on the Ene Reaction of Singlet Oxygen with 1,4-Cyclohexadienes?

The photooxygenation of 1,4-cyclohexadienes has been studied with a special focus on regio- and stereoselectivities. In all examples, only the methyl-substituted double bond undergoes an ene reaction with singlet oxygen, to afford hydroperoxides in moderate to good yields. We explain the high regioselectivities by a “large-group effect” of the adjacent quaternary stereocenter. Nitriles decrease the reactivity of singlet oxygen, presumably by quenching, but can stabilize proposed per-epoxide intermediates by polar interactions resulting in different stereoselectivities. Spiro lactams and lactones show an interesting effect on regio- and stereoselectivities of the ene reactions. Thus, singlet oxygen attacks the double bond preferentially anti to the carbonyl group, affording only one regioisomeric hydroperoxide. If the reaction occurs from the opposite face, the other regioisomer is exclusively formed by severe electrostatic repulsion in a perepoxide intermediate. We explain this unusual behavior by the fixed geometry of spiro compounds and call it a “spiro effect” in singlet oxygen ene reactions.

Synthesis method of 3-isochromanone

The invention belongs to the technical field of synthesis of organic intermediates, and particularly relates to a synthesis method of 3-isochromanone, which comprises the following steps of: (1) synthesizing o-methyl benzyl chloride by using o-xylene as a raw material; (2) synthesizing o-methyl benzyl cyanide by taking o-methyl benzyl chloride as a raw material; (3) synthesizing sodium o-methyl phenylacetate by taking o-methyl benzyl cyanide as a raw material; (4) synthesizing o-methyl phenylacetic acid by taking sodium o-methyl phenylacetate as a raw material; (5) synthesizing 2-chloromethylphenylacetic acid by taking o-methyl phenylacetic acid as a raw material; and (6) synthesizing 3-isochromanone by taking 2-chloromethyl phenylacetic acid as a raw material. The synthesis method of 3-isochromanone has the advantages of simple reaction process, easily available raw materials, mild reaction conditions, high product yield, low production cost, high yield, high product purity, good quality, low production waste discharge amount and the like, the product purity is greater than or equal to 99.5%, the production yield is greater than or equal to 92%, and the product meets the use requirements of foreign high-end users.

Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species

Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.

Titanium(III)-Catalyzed Reductive Decyanation of Geminal Dinitriles by a Non-Free-Radical Mechanism

A titanium-catalyzed mono-decyanation of geminal dinitriles is reported. The reaction proceeds under mild conditions, tolerates numerous functional groups, and can be applied to quaternary malononitriles. A corresponding desulfonylation is demonstrated as well. Mechanistic experiments support a catalyst-controlled cleavage without the formation of free radicals, which is in sharp contrast to traditional stoichiometric radical decyanations. The involvement of two TiIII species in the C?C cleavage is proposed, and the beneficial role of added ZnCl2 and 2,4,6-collidine hydrochloride is investigated.

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.

One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions

A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.

Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles

A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.

The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes

The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki-Miyaura cross coupling reaction followed by back-to-back C-H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access to a variety of unsymmetrical tri- and tetraarylmethane derivatives from simple, readily available starting materials. (Chemical Presented)

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.

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.