14476-72-3

Basic information

• Product Name: 2-(2-OXO-2-PHENYLETHYL)MALONONITRILE
• Synonyms: 2-(2-OXO-2-PHENYLETHYL)MALONONITRILE;OTAVA-BB 1060260;(2-oxo-2-phenylethyl)malononitrile
• CAS NO: 14476-72-3
• Molecular Formula: C₁₁H₈N₂O
• Molecular Weight: 184.19
• Mol File: 14476-72-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 148-149 °C
• Boiling Point: 399.3°C at 760 mmHg
• Flash Point: 195.3°C
• Appearance: /
• Density: 1.168g/cm³
• Vapor Pressure: 1.39E-06mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: 2-(2-OXO-2-PHENYLETHYL)MALONONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-OXO-2-PHENYLETHYL)MALONONITRILE(14476-72-3)
• EPA Substance Registry System: 2-(2-OXO-2-PHENYLETHYL)MALONONITRILE(14476-72-3)

Safety Data

• Hazardous Substances Data: 14476-72-3(Hazardous Substances Data)

Usage

General Description

2-(2-oxo-2-phenylethyl)malononitrile is a chemical compound with the molecular formula C13H9N3O2. It is a rare and potentially hazardous reagent, which is often used in organic synthesis. The compound is a derivative of malononitrile and features a phenylethyl moiety. It has been studied for its potential applications in the development of new materials and pharmaceuticals. However, its use is limited due to its toxicity and potential health hazards. Therefore, special care and precautions are necessary when handling this compound.

InChI:InChI=1/C11H8N2O/c12-7-9(8-13)6-11(14)10-4-2-1-3-5-10/h1-5,9H,6H2

Upstream product

• 70-11-1 α-bromoacetophenone 
• 4341-85-9 malonitrile 
• 105-36-2 ethyl bromoacetate 
• 109-77-3 malononitrile 

Downstream Products

• 122238-01-1 2-Amino-5-phenyl-1-p-tolyl-1H-pyrrole-3-carbonitrile 
• 158692-52-5 2-chloro-3-cyano-5-phenylpyrrole 
• 210347-38-9 3-oxo-6-phenyl-2,3,4,5-tetrahydropyridazine-4-carbonitrile 
• 1415477-06-3 C₂₂H₁₇N₅ 
• 1415477-01-8 C₁₆H₁₂N₄ 
• 1415477-02-9 C₁₆H₁₂N₄ 
• 1415477-03-0 C₁₇H₁₂BrN₃ 
• 1415477-08-5 C₂₃H₁₇BrN₄ 
• 1415477-10-9 C₂₃H₁₇ClN₄ 
• 1415477-11-0 C₂₃H₁₇ClN₄ 
• 1415477-05-2 C₁₉H₁₅N₅ 
• 1415477-13-2 C₂₅H₂₀N₆ 
• 14742-32-6 2-amino-5-phenylfuran-3-carbonitrile 

Relevant articles and documents

Synthesis of functionalized cyclopentenes through allenic ketone-based multicomponent reactions

A novel and efficient synthesis of diversely functionalized cyclopentene derivatives through the multicomponent reactions of 1,2-allenic ketones with 4-chloroacetoacetate and malononitrile/cyanoacetate under mild and metal-free conditions is presented. Me

A highly diastereoselective five-component synthesis of 1-(alkylimino)-5,5-dicyano-3a-aryloctahydro-3-oxacyclobuta[cd]pentalene-1a,2,5a,5b(2H,3aH)-tetracarboxylates

A novel one-pot, five-component synthesis of 1-(alkylimino)-5,5-dicyano-3a-aryloctahydro-3-oxacyclobuta[cd]pentalene-1a,2,5a,5b(2H,3aH)-tetracarboxylates is described. A mixture of phenacyl bromide, malononitrile, isocyanide, and two equivalents of a dial

Utility of pyrrole-2-thioacetohydrazide in synthesis of new heterocyclic compounds with promising antimicrobial activities and molecular docking studies

One-pot synthetic method for [(3-cyano-5-phenyl-1H-pyrrol-2-yl)sulfanyl]acetic acids 3a,b with excellent yield have been accomplished via a tetrabutylammonium bromide (TBAB) catalyzed reaction of mercaptoacetic acid with 2-(2-oxo-2-arylethyl) malononitrile under phase transfer catalysis conditions (PTC). The coupling of methyl [(3-cyano-5-phenyl-1H-pyrrol-2-yl)sulfanyl] acetate 4a,b with hydrazine gave the corresponding 2-[(3-cyano-5-aryl-1H-pyrrol-2yl)thio] acetohydrazides 5a,b, which reacted with glucose, acetylacetone, carbon disulfide, phenyl isothiocyanate, chloroacetyl chloride or benzaldehyde, to afford the compounds 6a,b–11a,b, respectively ranged from satisfactory to excellent yields. In vitro antibacterial and antifungal activities were assessed with good results. Furthermore, molecular docking experiments were done for the most active compounds against the E. coli MurB enzyme in order to determine the mechanism of their antibacterial activity and showed good binding interactions.

One-Step, Effective, and Cascade Syntheses of Highly Functionalized Cyclopentenes with High Diastereoselectivity

Tetrabutylammonium fluoride works as an effective organocatalyst for the cycloaddition between phenacylmalononitriles and electron-deficient olefins (having substituent groups of NO2, CHO, and COR), providing a facile synthetic route to versatile multifunctionalized cyclopentenes having an allylic quaternary carbon center bearing both cyano and carboxamide groups with high yields and high diastereoselectivity. Preliminary studies reveal that these functionalized cyclopentenes are convenient precursors for making α-cyano-functionalized cyclopentadienone oximes.