6453-98-1

Basic information

• Product Name: Phenyl(3-furyl) ketone
• Synonyms: 3-Benzoylfuran;Phenyl(3-furyl) ketone;3-Furanylphenylmethanone;3-Furfanylphenylmethanone;3-Furyl phenyl ketone;Brn 0121129;Ketone, 3-furyl phenyl;Methanone, 3-furfanylphenyl- (9ci)
• CAS NO: 6453-98-1
• Molecular Formula: C₁₁H₈O₂
• Molecular Weight: 172.19
• Mol File: 6453-98-1.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 262.49°C (rough estimate)
• Flash Point: 98.9°C
• Appearance: /
• Density: 1.1153 (rough estimate)
• Vapor Pressure: 0.0011mmHg at 25°C
• Refractive Index: 1.5520 (estimate)
• CAS DataBase Reference: Phenyl(3-furyl) ketone(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl(3-furyl) ketone(6453-98-1)
• EPA Substance Registry System: Phenyl(3-furyl) ketone(6453-98-1)

Safety Data

• Hazardous Substances Data: 6453-98-1(Hazardous Substances Data)

Usage

Safety Profile

A poison by intraperitoneal route. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating vapors.

InChI:InChI=1/C11H8O2/c12-8-9-3-1-4-10(7-9)11-5-2-6-13-11/h1-8H

Upstream product

• 26214-65-3 furan-3-carbonyl chloride 
• 2674-04-6 diphenyl cadmium 
• 1708-29-8 2,5-dihydrofuran 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 22037-28-1 3-bromofurane 
• 98-88-4 benzoyl chloride 
• 98-80-6 phenylboronic acid 
• 55552-70-0 furan-3-boronic acid 
• 488-93-7 3-Furoic acid 
• 6343-27-7 1-benzoylpyrrolidine-2,5-dione 
• 135364-97-5 tert-butyl benzoyl(tert-butoxycarbonyl)carbamate 
• 780-69-8 triethoxyphenylsilane 
• 19264-68-7 9-benzoyl-9H-carbazole 

Downstream Products

• 102029-10-7 [3]furyl-phenyl ketone-(4-phenyl semicarbazone) 
• 104919-77-9 Phenyl-(2,3,7-trioxa-bicyclo[2.2.1]hept-5-en-5-yl)-methanone 
• 104919-84-8 4-Benzoyl-5-hydroxy-5H-furan-2-one 
• 1428362-14-4 C₁₈H₁₆N₂O₃S 
• 1428339-05-2 3-((4-(tert-butyl)phenyl)(phenyl)methyl)furan 

Relevant articles and documents

Destannylative acylation of 1-[(2-methoxyethoxy)methoxy]-2- (phenylsulfonyl)-2-(tributylstannyl)cyclopropane: A novel route to 3- acylfurans

Destannylative acylation of 1-[(2-methoxyethoxy)methoxy]-2- (phenylsulfonyl)-2-(tributylstannyl)cyclopropane (1) provided dihydrofurans 5 in good yields, which upon treatment with BF3.OEt2 in CH2Cl2 led to the formation of 3-acylfurans 6 in moderate yields. The reaction was proposed to proceed via the intramolecular Prins-type reaction of the oxonium intermediate 7.

N-Acylcarbazoles and N-Acylindoles: Electronically Activated Amides for N-C(O) Cross-Coupling by Nlpto Ar Conjugation Switch

The development of new amide precursors for selective, catalytic activation of carbon-nitrogen bonds in amides is a fundamental objective of this emerging reactivity manifold. We report the palladium-catalyzed Suzuki-Miyaura cross-coupling of N-acylcarbazoles and N-acylindoles with arylboronic acids by a highly selective N-C(O) cleavage. The key amide bond ground-state destabilization stems from Nlp to Ar conjugation and enables us for the first time to achieve reactivity similar to that for N-acylsulfonamide and N-acylcarbamate activation in simple anilides.

Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP

An efficient and user-friendly palladium(II) precatalyst, POxAP (post-oxidative-addition precatalyst), was identified for use in Fukuyama cross-coupling reactions. Suitable for storage under air, the POxAP precatalyst allowed reaction between thioesters and organozinc reagents with turnover numbers of ～90000. A series of 23 ketones were obtained with yields ranging from 53 to 99%. As proof of efficacy, an alternative approach was developed for the synthesis of a key precursor of the natural product isoprekinamycin.