7153-22-2

Basic information

• Product Name: Ethyl 4-cyanobenzoate
• Synonyms: Benzoic acid, 4-cyano-, ethyl ester;P-CYANOBENZOIC ACID ETHYL ESTER;RARECHEM AL BI 0074;ETHYL 4-CYANOBENZOATE;4-CYANOBENZOIC ACID ETHYL ESTER;ethyl cyanobenzoate;Ethyl 4-cyanobenzoate,99%;Ethyl 4-cyanobenzoate 99%
• CAS NO: 7153-22-2
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• EINECS: 230-500-6
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Esters;C10 to C11;Carbonyl Compounds;Esters;Building Blocks;C10 to C11;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 7153-22-2.mol
• Article Data: 76

Chemical Properties

• Melting Point: 52-54 °C(lit.)
• Boiling Point: 140°C/11mmHg(lit.)
• Flash Point: >230 °F
• Appearance: white to light yellow crystalline powder
• Density: 1.1999 (rough estimate)
• Vapor Pressure: 0.00112mmHg at 25°C
• Refractive Index: 1.5060 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: Ethyl 4-cyanobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4-cyanobenzoate(7153-22-2)
• EPA Substance Registry System: Ethyl 4-cyanobenzoate(7153-22-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 7153-22-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystalline powder

InChI:InChI=1/C10H9NO2/c1-2-13-10(12)9-5-3-8(7-11)4-6-9/h3-6H,2H2,1H3

Upstream product

• 151-50-8 potassium cyanide 
• 94-09-7 p-aminoethylbenzoate 
• 125261-30-5 p-(ethoxycarbonyl)phenyl triflate 
• 16331-64-9 ethanolate 
• 32792-60-2 4-nitrophenyl 4-cyanobenzoate 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 36800-95-0 p-cyanophenyl p-toluenesulfonate 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 143-33-9 sodium cyanide 
• 23516-85-0 4-(2,2,2-trifluoroacetyl)benzonitrile 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 68-12-2 N,N-dimethyl-formamide 
• 141-78-6 ethyl acetate 

Downstream Products

• 101730-54-5 4-[(3,4-dimethoxy-phenylsulfanyl)-carboximidoyl]-benzoic acid ethyl ester 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 43038-36-4 4-cyanobenzohydrazide 
• 67052-28-2 ethyl 4-(aminocarbonyl)benzoate 
• 6287-86-1 p-ethoxycarbonylbenzaldehyde 
• 39895-56-2 4-hydroxymethyl-benzylamine 
• 366-84-7 ethyl 4-(aminomethyl)benzoate 
• 131065-88-8 N,N-bis(p-ethyloxycarbonylbenzyl)amine 
• 66631-28-5 4-carbethoxyimidobenzoesaeureethylester-hydrochloride 
• 61689-37-0 5-(4-ethoxycarbonyl-phenyl)-[1,2,4]thiadiazole-3-carboxylic acid ethyl ester 
• 40069-11-2 4-(Hydroxycarbamyl)-benzamidoxim 
• 6051-43-0 terephthalamic acid 
• 116655-43-7 4-((Z)-1-Hydroxy-2-pyrazin-2-yl-vinyl)-benzonitrile 
• 116655-39-1 4-(2-Quinoxalin-2-yl-acetyl)-benzonitrile 

Relevant articles and documents

Production of Copolyester Monomers from Plant-Based Acrylate and Acetaldehyde

PCTA is an important copolyester that has been widely used in our daily necessities. Currently, its monomers are industrially produced from petroleum-derived xylene. To reduce the reliance on fossil energy, we herein disclose an alternative route to acces

Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**

The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.

Zn-catalyzed cyanation of aryl iodides

We report the first example of zinc-catalyzed cyanation of aryl iodides with formamide as the cyanogen source. The transformation was promoted by the bisphosphine Nixantphos ligand. Under optimized conditions, a variety of electron-donating and electron-withdrawing aryl iodides were converted into nitrile products in good to excellent yields. This approach is an exceedingly simple and benign method for the synthesis of aryl nitriles and is likely to proceed via a dinuclear Zn-concerted catalysis.