3598-14-9

Basic information

• Product Name: PHENOXYACETONITRILE
• Synonyms: 2-PHENOXYACETONITRILE;PHENOXYACETONITRILE;Phenoxyacetonirile;Phenoxyacetonitrile,98%;Phenoxymethyl cyanide;Phenoxyacetonitrile 98%
• CAS NO: 3598-14-9
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.15
• Product Categories: Aromatic Nitriles;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 3598-14-9.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 235-238 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear light yellow-brown liquid
• Density: 1.09 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0381mmHg at 25°C
• Refractive Index: n20/D 1.524(lit.)
• Storage Temp.: 2-8°C
• BRN: 2206192
• CAS DataBase Reference: PHENOXYACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENOXYACETONITRILE(3598-14-9)
• EPA Substance Registry System: PHENOXYACETONITRILE(3598-14-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 3598-14-9(Hazardous Substances Data)

Usage

Description

Phenoxyacetonitrile, also known as 2-phenoxyacetonitrile, is an organic compound that serves as a versatile building block in the synthesis of various pharmaceutical and chemical products. It is a clear light yellow-brown liquid with unique chemical properties that make it suitable for a range of applications.

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

• 75-05-8 acetonitrile 
• 108-95-2 phenol 
• 100-66-3 methoxybenzene 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 590-17-0 cyanomethyl bromide 
• 98-80-6 phenylboronic acid 
• 13610-02-1 1-phenoxy-2-propyne 
• 1758-46-9 2-phenoxyethanamine 
• 3229-70-7 phenolate 
• 2120-70-9 2-phenoxyethanal 
• 139-02-6 sodium phenoxide 
• 32438-31-6 (2,2-diethoxy-ethoxy)-benzene 
• 2555-49-9 phenoxyacetic acid ethyl ester 

Downstream Products

• 161268-30-0 1-phenoxy-2-butanone 
• 103603-81-2 1-phenoxy-2-pentanone 
• 710328-89-5 4-methyl-1-phenoxy-pent-4-en-2-one 
• 859971-63-4 5-methyl-1-phenoxyhexan-2-one 
• 71617-04-4 1-phenoxyheptan-2-one 
• 721-04-0 2-phenoxy-1-phenylethanone 
• 24896-23-9 5-phenoxymethyltetrazole 
• 35370-80-0 2-phenoxyethanethioamide 
• 122-59-8 2-phenoxyacetic acid 
• 128277-13-4 4-Chloro-2-phenoxymethyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine 
• 128307-32-4 2-Phenoxymethyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ylamine 
• 57746-44-8 (2,4-dinitrophenyl)acetonitrile 
• 105199-28-8 (6-Nitro-5-quinolinyl)acetonitrile 
• 708-58-7 2-(4-fluoro-2-nitrophenyl)acetonitrile 

Relevant articles and documents

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.

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.

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.