3695-90-7

Basic information

• Product Name: (Z)-2-cyano-3-(furan-2-yl)acrylamide
• Synonyms: 2-Furanacrylamide, alpha-cyano-; 0-18-00-00339 (Beilstein Handbook Reference); 2-Propenamide, 2-cyano-3-(2-furanyl)-; BRN 0146815; F 2386; Furfural-cyanacetamid; Furfural-cyanacetamid [German]; alpha-Cyano-2-furanacrylamide; (2E)-2-cyano-3-(furan-2-yl)prop-2-enamide
• CAS NO: 3695-90-7
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.1454
• Mol File: 3695-90-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 391.6°C at 760 mmHg
• Flash Point: 190.6°C
• Density: 1.31g/cm³
• Vapor Pressure: 2.43E-06mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: (Z)-2-cyano-3-(furan-2-yl)acrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-cyano-3-(furan-2-yl)acrylamide(3695-90-7)
• EPA Substance Registry System: (Z)-2-cyano-3-(furan-2-yl)acrylamide(3695-90-7)

Safety Data

• Hazardous Substances Data: 3695-90-7(Hazardous Substances Data)

Usage

Description

(Z)-2-cyano-3-(furan-2-yl)acrylamide, also known as furfurylidenecyanoacrylamide, is a chemical compound with the molecular formula C9H7N3O2. It is a derivative of acrylamide and features a cyano group and a furan ring. (Z)-2-cyano-3-(furan-2-yl)acrylamide is known for its versatile applications in the synthesis of organic compounds, pharmaceuticals, and agrochemicals, as well as its potential in the development of new materials like polymers and hydrogels. Furthermore, it has been recognized for its antimicrobial properties, which have led to investigations into its use as an antimicrobial agent across various industries.

Uses

Used in Pharmaceutical Industry:
(Z)-2-cyano-3-(furan-2-yl)acrylamide is used as a building block for the synthesis of pharmaceuticals due to its unique chemical structure and reactivity. Its ability to form various organic compounds makes it a valuable asset in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, (Z)-2-cyano-3-(furan-2-yl)acrylamide is utilized as a key component in the creation of agrochemicals. Its chemical properties allow for the development of effective products for agricultural applications.
Used in Material Science:
(Z)-2-cyano-3-(furan-2-yl)acrylamide is used as a precursor in the development of new materials such as polymers and hydrogels. Its structural characteristics contribute to the advancement of material science by enabling the creation of innovative and improved materials with potential applications in various fields.
Used as an Antimicrobial Agent:
(Z)-2-cyano-3-(furan-2-yl)acrylamide is used as an antimicrobial agent in various applications due to its antimicrobial properties. It has the potential to be incorporated into products to prevent the growth of harmful microorganisms, thereby enhancing the safety and longevity of these products.
Used in Research and Development:
(Z)-2-cyano-3-(furan-2-yl)acrylamide is also used in research and development settings as a compound of interest for scientists exploring new chemical reactions, synthesis methods, and potential applications in various industries. Its unique properties make it a valuable tool for advancing scientific knowledge and innovation.

Upstream product

• 98-01-1 furfural 
• 107-91-5 cyanoacetic acid amide 
• 3237-22-7 2-cyano-3-(2-furanyl)acrylonitrile 
• 50-00-0 formaldehyd 
• 3533-10-6 3-(2-chlorophenyl)-2-cyanoprop-2-enamide 
• 106-49-0 p-toluidine 
• 109-77-3 malononitrile 
• 222179-55-7 2-[furan-2-yl(hydroxy)methyl]prop-2-enoate nitrile 
• 148840-19-1 (E)-2-formyl-3-(furan-2-yl)acrylonitrile 
• 617-89-0 furan-2-ylmethanamine 

Downstream Products

• 77607-74-0 4-(furan-2-yl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile 
• 177937-80-3 4-Furan-2-yl-5-methyl-2-oxo-6-phenyl-1,2-dihydro-pyridine-3-carbonitrile 

Relevant articles and documents

Enantioselective ene-reduction of E-2-cyano-3-(furan-2-yl) acrylamide by marine and terrestrial fungi and absolute configuration of (R)-2-cyano-3-(furan-2-yl) propanamide determined by calculations of electronic circular dichroism (ECD) spectra

This work reports the green organic chemistry synthesis of E-2-cyano-3(furan-2-yl) acrylamide under microwave radiation (55?W), as well as the use of filamentous marine and terrestrial-derived fungi, in the first ene-reduction of 2-cyano-3-(furan-2-yl) acrylamide to (R)-2-cyano-3-(furan-2-yl)propanamide. The fungal strains screened included Penicillium citrinum CBMAI 1186, Trichoderma sp. CBMAI 932 and Aspergillus sydowii CBMAI 935, and the filamentous terrestrial fungi Aspergillus sp. FPZSP 146 and Aspergillus sp. FPZSP 152. A compound with an uncommon CN-bearing stereogenic center at the α-C position was obtained by enantioselective reactions mediated in the presence of the microorganisms yielding the (R)-2-cyano-3-(furan-2-yl) propanamide 3a. Its isolated yield and e.e. ranged from 86% to 98% and 39% to 99%, respectively. The absolute configuration of the biotransformation products was determined by time-dependent density functional theory (TD-DFT) calculations of electronic circular dichroism (ECD) spectra. Finally, the tautomerization of 2-cyano-3-(furan-2-yl) propanamide 3a to form an achiral ketenimine was observed and investigated in presence of protic solvents.

Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles

A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions wit

An efficient catalyst-free one-pot synthesis of primary amides from the aldehydes of the Baylis-Hillman reaction

Herein, a facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis-Hillman adducts has been developed using a hydroxylamine/methanol system under a catalyst-free condition. The effects of solvents and temperature on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its advantages such as operational simplicity, moderate to excellent yields, short reaction time, and simple reaction procedure. Most importantly, the reaction proceeds smoothly in the absence of a catalyst and an external oxidant.