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
• Article Data: 24

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

Description

2-Methylbenzyl cyanide, also known as o-Tolylacetonitrile, is a nitrile derivative where one of the methyl hydrogens in acetonitrile is substituted by a 2-methylphenyl group. It is characterized by its clear colorless to orange-reddish liquid appearance and is widely recognized for its significance in various industrial applications.

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.

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.