3598-14-9

Usage

Uses

Used in Pharmaceutical Industry:
Phenoxyacetonitrile is used as a reactant for the preparation of [[(oxo)pyridazinyl]phenoxy]acetonitrile derivatives, which are known to have vasodilatory effects. These derivatives are valuable in the treatment of cardiovascular diseases, as they help in the relaxation of blood vessels, thereby improving blood flow and reducing blood pressure.
Used in Chemical Synthesis:
Phenoxyacetonitrile is utilized in the synthesis of various compounds, such as 2,4-dihydroxyphenoxyacetophenones, methylthio(phenoxy)acetonitrile, and 2,4-diamino-5-(3,4,5-trimethoxyphenoxy)pyrimidine. These synthesized compounds have potential applications in different industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H7NO/c9-6-7-10-8-4-2-1-3-5-8/h1-5H,7H2

Upstream product

• 621-88-5 phenoxyacetamide 
• 107-14-2 chloroacetonitrile 
• 108-95-2 phenol 
• 122-59-8 2-phenoxyacetic acid 
• 32438-31-6 (2,2-diethoxy-ethoxy)-benzene 
• 2120-70-9 2-phenoxyethanal 
• 1758-46-9 2-phenoxyethanamine 
• 75-05-8 acetonitrile 
• 701-99-5 Phenoxyacetyl chloride 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 100-66-3 methoxybenzene 
• 590-17-0 cyanomethyl bromide 
• 98-80-6 phenylboronic acid 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 

Downstream Products

• 851443-13-5 1-phenoxy-hexan-2-one 
• 67386-33-8 2-phenoxy-acetimidic acid ethyl ester; hydrochloride 
• 35855-76-6 1-phenoxy-3-phenylpropan-2-one 
• 15485-59-3 1-Phenoxy-5-dimethylamino-pentanon-⁽²⁾ 
• 19450-48-7 N-(Octahydro-naphthalen-4a-yl)-2-phenoxy-acetamide 
• 741222-44-6 2-Phenoxy-acetimidic acid methyl ester 
• 136346-92-4 (Z)-5-Amino-2,2-dimethyl-6-phenoxy-hex-4-en-3-one 
• 73023-07-1 2-phenoxy-1-(2,4,6-trihydroxyphenyl)ethanone 
• 105214-06-0 2-(8-nitroquinolin-7-yl)acetonitrile 
• 105199-23-3 (5-Nitro-6-quinolinyl)acetonitrile 
• 105199-28-8 (6-Nitro-5-quinolinyl)acetonitrile 
• 89277-98-5 2-(2-chloro-6-nitrophenyl)acetonitrile 
• 87081-90-1 (4-chloro-2-nitro-phenyl)-acetonitrile 
• 119679-96-8 (5-benzoyl-2-nitrophenyl)(phenoxy)acetonitrile 

Relevant academic research and scientific papers

Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.

Synthesis of aryloxyacetonitriles based on arylboronic acids with 2-bromoacetonitrile

A new and efficient protocol for the synthesis of aryloxyacetonitriles based on arylboronic acids with 2-bromoacetonitrile has been developed using eco-friendly hydrogen peroxide as oxidant under metal-free conditions. This method is compatible with arylboronic acid attached sensitive substituent and obtains desired product in moderate to good yield.

IODONIUM SALT COMPOUND, PHOTOACID GENERATOR AND COMPOSITION CONTAINING THE SAME, AND METHOD FOR MANUFACTURING DEVICE

PROBLEM TO BE SOLVED: To provide an iodonium salt compound which can be used as a chemical amplification type photoacid generator for resist and a photocationic polymerization initiator, has high sensitivity to an i-line at a wavelength of 365 nm, and has high solubility to an organic solvent and a resin. SOLUTION: A new iodonium salt compound is represented by the following iodonium salts 2, 5 and 10. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2019,JPOandINPIT

Dehydration of Amides to Nitriles under Conditions of a Catalytic Appel Reaction

A highly expedient protocol for a catalytic Appel-type dehydration of amides to nitriles has been developed that employs oxalyl chloride and triethylamine along with triphenylphosphine oxide as a catalyst. The reactions are usually complete in less than 10 min with only a 1 mol % catalyst loading. The reaction scope includes aromatic, heteroaromatic, and aliphatic amides, including derivatives of α-hydroxy and α-amino acids.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

Synthesis of Nitriles from Primary Amides or Aldoximes under Conditions of a Catalytic Swern Oxidation

The preparation of nitriles from primary amides or aldoximes was achieved by using oxalyl chloride with a catalytic amount of dimethyl sulfoxide in the presence of Et3N. The reactions were complete within 1 h after addition at room temperature. A diverse range of cyano compounds were obtained in good to excellent yields, including aromatic, heteroaromatic, cyclic, and acyclic aliphatic species.

A metal-free direct C (sp3)-H cyanation reaction with cyanobenziodoxolones

A metal-free protocol of direct C(sp3)-H cyanation with cyanobenziodoxolones functioning as both cyanating reagents and oxidants was developed. Unactivated substrates, such as alkanes, ethers and tertiary amines, were thereby transformed to the corresponding nitriles in moderate to high yields. Mechanistic studies indicated that the cyanation proceeded with two potential pathways, which is highly dependent on the substrates: (1) a free radical case for alkanes and ethers and (2) an oxidative case for tertiary amines.

A mineralogically-inspired silver-bismuth hybrid material: An efficient heterogeneous catalyst for the direct synthesis of nitriles from terminal alkynes

The synthesis and characterization of a silver-containing hybrid material is reported as a novel heterogeneous noble metal catalyst. In order to eliminate the need for traditional immobilization techniques, and to create a solid material with structurally-bound silver catalytic centers, the layered structure of a naturally occurring mineral served as the basis of the initial catalyst design. The novel material was prepared by means of the urea-mediated homogeneous precipitation of the corresponding metal nitrates, and was fully characterized by means of diverse instrumental techniques (X-ray diffractometry, Raman, IR, UV-Vis, EPR, X-ray photoelectron spectroscopies, thermal methods as well as atomic force, scanning and transmission electron microscopies). The as-prepared material exhibited outstanding activity in silver-catalyzed CC bond activation to yield organic nitriles directly from terminal alkynes with less environmental concerns as compared to the classical synthesis methods. The effects of the reaction time, the temperature, as well as the role of various solvents, nitrogen sources and additives were carefully scrutinized in order to achieve high-yielding and selective nitrile formation. The heterogeneous nature of the reaction was verified and the solid catalyst was recycled and reused numerous times without loss of its activity or degradation of its structure, thereby offering a sustainable synthetic methodology.

One-pot conversion of aldehydes to nitriles mediated by TiCl4

A simple and convenient one-pot synthesis of nitriles from the corresponding aliphatic and aromatic aldehydes has been developed. The titanium tetrachloride assisted reaction was conducted in pyridine under mild conditions using various types of aldehyde precursors and gave the corresponding nitriles in excellent yields. The application of the adopted protocol to isolated aldoxime intermediates provided the corresponding nitriles with yields comparable to those using the one-pot procedure.

Synthesis of nitriles from amines using nanoscale Co3O4-based catalysts via sustainable aerobic oxidation

The selective oxidation of amines for the benign synthesis of nitriles under mild conditions is described. Key to success for this transformation is the application of reusable cobalt oxide-based nanocatalysts. The resulting nitriles constitute key precursors and central intermediates in organic synthesis.