17275-73-9

Basic information

• Product Name: 2-Furanmethanol, a-methyl-a-(phenylmethyl)-
• CAS NO: 17275-73-9
• Molecular Formula: C13H14O2
• Molecular Weight: 202.253
• Mol File: 17275-73-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-Furanmethanol, a-methyl-a-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Furanmethanol, a-methyl-a-(phenylmethyl)-(17275-73-9)
• EPA Substance Registry System: 2-Furanmethanol, a-methyl-a-(phenylmethyl)-(17275-73-9)

Safety Data

• Hazardous Substances Data: 17275-73-9(Hazardous Substances Data)

Usage

General Description

2-Furanmethanol, a-methyl-a-(phenylmethyl)- is a chemical compound that is commonly used as a flavoring agent and fragrance ingredient. It is a colorless liquid with a sweet, somewhat floral odor. It is used in various food and beverage products as a flavor enhancer and also in the production of perfumes and other scented products. However,

Upstream product

• 1192-62-7 1-(2-furyl)-1-ethanone 
• 1589-82-8 phenylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 5281-18-5 benzaldehyde, hydrazone 
• 6137-68-4 2-(prop-1-en-2-yl)furan 
• 100-63-0 phenylhydrazine 

Relevant articles and documents

Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds

Nucleophilic addition reactions of organometallic reagents to carbonyl compounds for carbon-carbon bond construction have played a pivotal role in modern chemistry. However, this reaction's reliance on petroleum-derived chemical feedstocks and a stoichiometric quantity of metal have prompted the development of many carbanion equivalents and catalytic metal alternatives. Here, we show that naturally occurring carbonyls can be used as latent alkyl carbanion equivalents for additions to carbonyl compounds, via reductive polarity reversal. Such 'umpolung' reactivity is facilitated by a ruthenium catalyst and diphosphine ligand under mild conditions, delivering synthetically valuable secondary and tertiary alcohols in up to 98% yield. The unique chemoselectivity exhibited by carbonyl-derived carbanion equivalents is demonstrated by their tolerance to protic reaction media and good functional group compatibility. Enantioenriched tertiary alcohols can also be accessed with the aid of chiral ligands, albeit with moderate stereocontrol. Such carbonyl-derived carbanion equivalents are anticipated to find broad utility in chemical bond formation.