2689-59-0

Basic information

• Product Name: 2-furyl phenyl ketone
• Synonyms: 2-benzoylfuran;2-furyl phenyl ketone;(2-Furanyl) phenyl ketone;Phenyl (2-furyl) ketone;Phenyl 2-furyl ketone;furan-2-yl(phenyl)methanone
• CAS NO: 2689-59-0
• Molecular Formula: C₁₁H₈O₂
• Molecular Weight: 172.18
• Mol File: 2689-59-0.mol
• Article Data: 116

Chemical Properties

• Boiling Point: 285°C (estimate)
• Flash Point: 129°C
• Appearance: /
• Density: 1.1732
• Vapor Pressure: 0.00276mmHg at 25°C
• Refractive Index: 1.6055 (estimate)
• CAS DataBase Reference: 2-furyl phenyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-furyl phenyl ketone(2689-59-0)
• EPA Substance Registry System: 2-furyl phenyl ketone(2689-59-0)

Safety Data

• Hazardous Substances Data: 2689-59-0(Hazardous Substances Data)

Usage

General Description

2-furyl phenyl ketone, also known as 2-furyl benzophenone, is a chemical compound with the molecular formula C19H14O. It is a yellow crystalline solid with a sweet, floral aroma, and is commonly used in the production of perfumes and fragrance products. The compound is also found in some natural products, such as the essential oil of Costus oil, and has been identified as a potential bioactive molecule with anti-inflammatory and antioxidant properties. Additionally, 2-furyl phenyl ketone is used as a UV absorber in sunscreen and skincare products due to its ability to block harmful UV radiation. However, it is important to note that this compound should be handled with care as it may be harmful if ingested, inhaled, or comes into contact with skin and eyes.

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

Upstream product

• 72667-24-4 Brenzschleimsaeurenitril 
• 527-69-5 2-furancarbonyl chloride 
• 133071-19-9 Dimethyl-[8-(methyl-diphenyl-stannanyl)-naphthalen-1-yl]-amine 
• 587-85-9 diphenylmercury(II) 
• 60907-91-7 2-furyl(phenyl)methanol 
• 143-66-8 sodium tetraphenyl borate 
• 13331-23-2 fur-2-ylboronic acid 
• 65-85-0 benzoic acid 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 17920-86-4 di-furan-2-yl-methanone 
• 98-80-6 phenylboronic acid 
• 28557-00-8 phenylzinc chloride 
• 98-01-1 furfural 

Downstream Products

• 51937-70-3 (5-nitro-furan-2-yl)-phenyl-methanone 
• 65-85-0 benzoic acid 
• 968-68-3 1-furan-2-yl-4-morpholin-4-yl-1-phenyl-but-2-yn-1-ol 

Relevant articles and documents

Asymmetric Transfer Hydrogenation of Aryl Heteroaryl Ketones using Noyori-Ikariya Catalysts

A range of ketones flanked by a combination of an aromatic and a heterocyclic ring (furan, thiophene, N-methylimidazole) were reduced under asymmetric transfer hydrogenation (ATH) conditions. Using a range of [(arene)Ru(TsDPEN)Cl] precatalysts, including tethered derivatives, the reduction enantioselectivity was high (up to 99 % ee) in cases where the aromatic ring contained an ortho-substituent. The enantioselectivity is influenced by a combination of steric and electronic factors which for the furan and thiophene series, follow literature precedents. In the case of the N-methylimidazole-containing ketones, an unexpected switch in enantioselectivity took place upon variation of the opposing aromatic group. Pyrrole- containing ketones were resistant to reduction. This study demonstrates the asymmetric transfer hydrogenation (ATH) of a range of hindered heterocyclic ketones, in high conversion and ee, using Noyori-Ikariya catalysts.

Evaluation of Cyclic Amides as Activating Groups in N-C Bond Cross-Coupling: Discovery of N-Acyl-δ-valerolactams as Effective Twisted Amide Precursors for Cross-Coupling Reactions

The development of efficient methods for facilitating N-C(O) bond activation in amides is an important objective in organic synthesis that permits the manipulation of the traditionally unreactive amide bonds. Herein, we report a comparative evaluation of a series of cyclic amides as activating groups in amide N-C(O) bond cross-coupling. Evaluation of N-acyl-imides, N-acyl-lactams, and N-acyl-oxazolidinones bearing five- and six-membered rings using Pd(II)-NHC and Pd-phosphine systems reveals the relative reactivity order of N-activating groups in Suzuki-Miyaura cross-coupling. The reactivity of activated phenolic esters and thioesters is evaluated for comparison in O-C(O) and S-C(O) cross-coupling under the same reaction conditions. Most notably, the study reveals N-acyl-δ-valerolactams as a highly effective class of mono-N-acyl-activated amide precursors in cross-coupling. The X-ray structure of the model N-acyl-δ-valerolactam is characterized by an additive Winkler-Dunitz distortion parameter ?(τ+χN) of 54.0°, placing this amide in a medium distortion range of twisted amides. Computational studies provide insight into the structural and energetic parameters of the amide bond, including amidic resonance, N/O-protonation aptitude, and the rotational barrier around the N-C(O) axis. This class of N-acyl-lactams will be a valuable addition to the growing portfolio of amide electrophiles for cross-coupling reactions by acyl-metal intermediates.

Direct Access to α,β-Unsaturated Ketones via Rh/MgCl2-Mediated Acylation of Vinylsilanes

We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized with synthetically useful yield.