144464-70-0

Basic information

• Product Name: 1-Propanone, 2,2-difluoro-1-(4-methoxyphenyl)- (9CI)
• Synonyms: 1-Propanone, 2,2-difluoro-1-(4-methoxyphenyl)- (9CI)
• CAS NO: 144464-70-0
• Molecular Formula: C₁₀H₁₀F₂O₂
• Molecular Weight: 200.1820064
• Product Categories: ACETYLHALIDE
• Mol File: 144464-70-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Propanone, 2,2-difluoro-1-(4-methoxyphenyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanone, 2,2-difluoro-1-(4-methoxyphenyl)- (9CI)(144464-70-0)
• EPA Substance Registry System: 1-Propanone, 2,2-difluoro-1-(4-methoxyphenyl)- (9CI)(144464-70-0)

Safety Data

• Hazardous Substances Data: 144464-70-0(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 28781-85-3 ethyl 2,2-difluoropropanoate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 55991-65-6 [1-(4-methoxyphenyl)vinyloxy]trimethylsilane 
• 14774-77-7 p-methoxyphenyllithium 

Downstream Products

• 144464-78-8 methyl 4,4-difluoro-3-(4-methoxyphenyl)-2-pentenoate, (Z)-isomer 
• 144464-77-7 methyl 4,4-difluoro-3-(4-methoxyphenyl)-2-pentenoate, (E)-isomer 
• 144464-72-2 (Z)-4,4-Difluoro-3-(4-methoxy-phenyl)-pent-2-enoic acid ethyl ester 
• 144464-71-1 ethyl (E)-4,4-difluoro-3-(p-methoxyphenyl)pent-2-enoate 
• 167168-01-6 ethyl 4,4-difluoro-3-(p-methoxyphenyl)pentanoate 

Relevant articles and documents

FLUORINATING AGENT AND METHOD FOR PRODUCING FLUORINE-CONTAINING COMPOUNDS

The present invention provides the compound represented in general formula (A1) [Ar1 is a C6-14 aryl group or a C5-14 nitrogen-containing heteroaryl group, substituted with at least two electron-attracting groups; R1 is a C1-30 alkyl group, a C6-14 aryl group, or a C5-14 nitrogen-containing heteroaryl group; the electron-attracting group is a halogen atom, a trihalomethyl group, a cyano group, a nitro group, -CO2R or -CO2N(R)2 (the Rs independently represent C1-30 alkyl groups)].

Bench-Stable Electrophilic Fluorinating Reagents for Highly Selective Mono- and Difluorination of Silyl Enol Ethers

Efficient methods for the synthesis of fluorinated compounds have been intensively studied, recently. Development of practical fluorinating reagents is indispensable for this purpose. Herein, bench-stable electrophilic fluorinating reagents were synthesized as N-fluorobenzenesulfonimide (NFSI) substitutes. Reagents obtained by replacing one of the NFSI sulfonyl groups with an acyl group led to the highly selective monofluorination of silyl enol ethers with suppression of undesired overreaction, that is, difluorination. On the other hand, reagents bearing electron-withdrawing substituents at NFSI benzenesulfonyl groups efficiently facilitated the difluorination of silyl enol ethers under base-free conditions. Thus, both mono- and difluorinated target materials were prepared from the same substrate.

Practical Access to Difluoromethyl Ketones via Straightforward Decarboxylative Difluorination of β-Ketoacids

A facile synthetic approach to a series of difluoromethyl ketones from β-ketoacids has been described. This transformation is achieved through the straightforward decarboxylative difluorination of β-ketoacids in the absence of any catalyst. Furthermore, the resulted difluoromethyl ketones can be easily converted into corresponding difluoromethylated building blocks for pharmaceuticals and materials. (Figure presented.).

Difluorohomologation of ketones

A method for the homologation of ketones with the CF2 fragment is described. The reaction involves silylation, room-temperature difluorocyclopropanation of silyl enol ethers, and selective ring opening of cyclopropanes under acidic conditions. The whole three-step sequence is conveniently performed in a one-pot mode.

Synthesis of DL-threo-3-(1-fluoro-1-methylethyl)- and DL-threo-3-(1,1-difluoroethyl)malic acids. Machanistic studies of 3-isopropylmalate dehydrogenase

For both mechanistic studies and the development of novel inhibitors of 3-isopropylmalate dehydrogenase enzyme (IPMDH), which is involved in the rate-determining step in the biosynthesis pathway of the essential amino acid L-leucine, (2R*,3S*)-3-(1-fluoro-1-methylethyl)- and (2R*,3S*)-3-(1,1-difluoroethyl)malic acids (F-IPM and F2-EM) were designed based on the concept of mechanism-based inhibition, and the reaction kinetics with these fluorinated substrates were analysed.The reaction of F-IPM with IPMDH was studied by NMR spectroscopy and product isolation.F-IPM underwent, after the normal enzyme reaction, the expected additional elimination reaction to afford an α,β-unsaturated carbonyl product, which turned out not to participate in any covalen-bond-forming reaction.The conformation of the reaction intermediate during the IPMDH reaction and the functional-group arrangement in the active site of IPMDH are discussed.

Remarkable reversal of stereoselectivity in Wittig-type olefinations of α-fluorinated alkyl aryl ketones

Remarkable reactivity and reversal of stereoselectivity in the Wittig-type olefinations of α-fluorinated alkyl aryl ketones were described. Stabilized Wittig and Horner-Emmons reagents with these ketones selectively afforded the olefinic products in the stereochemically opposite fashion to the non-fluorinated ketone cases. The Still's reagent further reversed the stereochemical outcome with the fluorinated ketones.