52805-36-4

Basic information

• Product Name: 4-BENZYLOXYBENZONITRILE
• Synonyms: 4-BENZYLOXYBENZONITRILE;4-Cyanophenylbenzyl ether
• CAS NO: 52805-36-4
• Molecular Formula: C₁₄H₁₁NO
• Molecular Weight: 209.24
• EINECS: -0
• Product Categories: Aromatic Nitriles;Benzonitriles (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials
• Mol File: 52805-36-4.mol
• Article Data: 109

Chemical Properties

• Melting Point: 94 °C
• Boiling Point: 173-175°C 0,1mm
• Flash Point: 173-175°C/0.1mm
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 8.61E-06mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: almost transparency in hot Methanol
• BRN: 2372698
• CAS DataBase Reference: 4-BENZYLOXYBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXYBENZONITRILE(52805-36-4)
• EPA Substance Registry System: 4-BENZYLOXYBENZONITRILE(52805-36-4)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39-36
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 52805-36-4(Hazardous Substances Data)

Usage

General Description

4-Benzyloxybenzonitrile, also known as 4-(Benzyloxy)benzonitrile, is a chemical compound with the molecular formula C14H11NO. It is a white to light yellow crystalline solid with a molecular weight of 209.24 g/mol. 4-Benzyloxybenzonitrile is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is also used as a building block for the production of dyes and other fine chemicals. The compound is generally stable under normal conditions, but it may react with strong oxidizing agents and can release toxic fumes when heated to decomposition. 4-Benzyloxybenzonitrile should be handled and stored according to the proper safety precautions and guidelines.

InChI:InChI=1/C14H11NO/c15-10-12-6-8-14(9-7-12)16-11-13-4-2-1-3-5-13/h1-9H,11H2

Upstream product

• 4397-53-9 p-benzyloxybenzaldehyde 
• 86120-19-6 O-benzyl oxime of 4-nitrobenzaldehyde 
• 100-39-0 benzyl bromide 
• 767-00-0 4-cyanophenol 
• 1129-37-9 4-nitrobenzaldehyde oxime 
• 14609-76-8 4-cyanophenolate 
• 100-44-7 benzyl chloride 
• 3328-57-2 sodium 4-cyanophenolate 
• 188038-47-3 3'-[4-(phenylmethoxy)phenyl][5,6]fullereno-C₆₀-I_h-[1,9-d]isoxazole 
• 100-51-6 benzyl alcohol 
• 623-00-7 4-bromobenzenecarbonitrile 
• 620-05-3 iodomethylbenzene 
• 76193-67-4 4-benzyloxybenzaldehyde oxime 
• 19578-68-8 4-(4-benzyloxyphenyl) iodide 

Downstream Products

• 767-00-0 4-cyanophenol 
• 57928-60-6 C₁₄H₁₄N₂O*1.16ClH 
• 13031-41-9 4-cyanophenyl acetate 
• 151250-16-7 2-(4-benzyloxyphenyl)-4,5-dihydrooxazole 
• 844879-58-9 3-(4-benzyloxyphenyl)-1H-1,2,4-triazole 
• 1353639-21-0 C₃₂H₃₀N₂O₂ 
• 552854-22-5 C₂₅H₂₄N₂O₂ 
• 1353639-22-1 C₃₂H₃₆N₂O₄ 
• 1353639-29-8 C₃₈H₄₈N₂O₄ 
• 1353639-28-7 C₃₀H₃₂N₂O₄ 
• 1353639-30-1 C₃₆H₄₄N₂O₄ 

Relevant articles and documents

Nitrile Synthesis via Desulfonylative-Smiles Rearrangement

Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.

Photocatalytic Reductive C-O Bond Cleavage of Alkyl Aryl Ethers by Using Carbazole Catalysts with Cesium Carbonate

Methods to activate the relatively stable ether C-O bonds and convert them to other functional groups are desirable. One-electron reduction of ethers is a potentially promising route to cleave the C-O bond. However, owing to the highly negative redox potential of alkyl aryl ethers (Ered -2.6 V vs SCE), this mode of ether C-O bond activation is challenging. Herein, we report the visible-light-induced photocatalytic cleavage of the alkyl aryl ether C-O bond using a carbazole-based organic photocatalyst (PC). Both benzylic and non-benzylic aryl ethers underwent C-O bond cleavage to form the corresponding phenol products. Addition of Cs2CO3 was beneficial, especially in reactions using a N-H carbazole PC. The reaction was proposed to occur via single-electron transfer (SET) from the excited-state carbazole to the substrate ether. Interaction of the N-H carbazole PC with Cs2CO3 via hydrogen bonding exists, which enables a deprotonation-assisted electron-transfer mechanism to operate. In addition, the Lewis acidic Cs cation interacts with the substrate alkyl aryl ether to activate it as an electron acceptor. The high reducing ability of the carbazole combined with the beneficial effects of Cs2CO3 made this otherwise formidable SET event possible.

CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source

Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.