2-(o-Tolyl)acetonitrile, CAS No. 22364-68-7

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22364-68-7

Catalog No. EBD24825

CAS 22364-68-7

Name 2-(o-Tolyl)acetonitrile

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Basic Information

Synonyms: 2-Methylphenylacetonitrile o-methylbenzylcyanide Tolylacetonitrile N,N'-propane-1,3-diylbis(2-chloroacetamide) orthomethylbenzylcyanide 2-Methylbenzylcyanide o-Methylphenylacetonitrile 2-(o-Tolyl)acetonitrile o-tolylacetonitrile

Molecular Formula: C9H9N

Molecular Weight: 131.17

MDL Number: MFCD00001904

Categories: Synthetic Chemistry > Organic Building Blocks > Cyano Compounds Synthetic Chemistry > Basic Synthetic Reagents > Other Basic Synthetic Reagents

Product Description:

O-Methylbenzonitrile oxide is a reactive 1,3-dipole belonging to the nitrile oxide family. It is characterized by the presence of a nitrile oxide functional group (-C≡N⁺-O⁻) attached to a benzene ring. This compound is typically generated in situ from its stable precursor, such as the corresponding hydroximoyl chloride, under basic conditions. Its primary application is in synthetic organic chemistry as a key reagent for 1,3-dipolar cycloaddition reactions, most notably with alkynes and alkenes to form isoxazoles and isoxazolines, respectively. These heterocyclic scaffolds are important structural motifs found in numerous pharmaceuticals, agrochemicals, and functional materials. The reaction with O-methylbenzonitrile oxide is a fundamental method for constructing these five-membered rings with high regioselectivity. Due to its high reactivity and tendency to dimerize, it is not commonly isolated or stored. Instead, it is prepared immediately before use. Its role is almost exclusively confined to being a specialized synthetic building block and reagent in research and development laboratories for the construction of complex molecular architectures.

Physical Properties

Boiling Point: 244-250 °C

Flash Point: >110°C

Density: 1.05

Solubility: soluble in benzene, ethyl ether, ethanol

Refractivity: 1.5264-1.5284

Analytical Data

Appearance: clear colorless to orange-reddish liquid