59872-84-3

Basic information

• Product Name: PENTAFLUOROPROPIONALDEHYDE METHYL HEMIACETAL
• Synonyms: 1-METHOXY-1H-PENTAFLUOROPROPANOL;PENTAFLUOROPROPIONALDEHYDE METHYL HEMIACETAL;2,2,3,3,3-pentafluoro-1-methoxy-1-propano;2,2,3,3,3-pentafluoro-1-methoxypropanol;PENTAFLUOROPROPIONALDEHYDE METHYL HEMIACETAL 97%;2,2,3,3,3-Pentafluoro-1-methoxy-1-propanol;1-Propanol, 2,2,3,3,3-pentafluoro-1-methoxy-;Einecs 261-970-0
• CAS NO: 59872-84-3
• Molecular Formula: C₄H₅F₅O₂
• Molecular Weight: 180.07
• EINECS: 261-970-0
• Mol File: 59872-84-3.mol

Chemical Properties

• Boiling Point: 81 °C at 760 mmHg
• Flash Point: 44.1 °C
• Appearance: /
• Density: 1.427 g/cm³
• Vapor Pressure: 55mmHg at 25°C
• Refractive Index: 1.313
• CAS DataBase Reference: PENTAFLUOROPROPIONALDEHYDE METHYL HEMIACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAFLUOROPROPIONALDEHYDE METHYL HEMIACETAL(59872-84-3)
• EPA Substance Registry System: PENTAFLUOROPROPIONALDEHYDE METHYL HEMIACETAL(59872-84-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 59872-84-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
PENTAFLUOROPROPIONALDEHYDE METHYL HEMIACETAL is used as a key intermediate in the synthesis of various pharmaceutical compounds for its reactivity and unique properties that contribute to the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, PENTAFLUOROPROPIONALDEHYDE METHYL HEMIACETAL is utilized as a precursor in the production of agrochemicals, aiding in the creation of effective and novel pesticides or other agricultural chemicals.
Used in Specialty Chemicals Production:
PENTAFLUOROPROPIONALDEHYDE METHYL HEMIACETAL is used as a versatile building block in the synthesis of specialty chemicals, providing unique properties that enhance the performance of these chemicals in specific applications.
Used as a Solvent or Reagent:
Due to its reactivity, PENTAFLUOROPROPIONALDEHYL METHYL HEMIACETAL is also employed as a solvent or reagent in organic synthesis, facilitating various chemical reactions in research and industrial processes.

InChI:InChI=1/C4H5F5O2/c1-11-2(10)3(5,6)4(7,8)9/h2,10H,1H3

Upstream product

• 378-75-6 perfluoropropionic acid methyl ester 

Downstream Products

• 80967-57-3 cyclohexanecarboxylic acid (2,2,3,3,3-pentafluoropropylidene)hydrazide 

Relevant articles and documents

Engineering Catalysts for Selective Ester Hydrogenation

The development of efficient catalysts and processes for synthesizing functionalized (olefinic and/or chiral) primary alcohols and fluoral hemiacetals is currently needed. These are valuable building blocks for pharmaceuticals, agrochemicals, perfumes, and so forth. From an economic standpoint, bench-stable Takasago Int. Corp.'s Ru-PNP, more commonly known as Ru-MACHO, and Gusev's Ru-SNS complexes are arguably the most appealing molecular catalysts to access primary alcohols from esters and H2 (Waser, M. et al. Org. Proc. Res. Dev. 2018, 22, 862). This work introduces economically competitive Ru-SNP(O)z complexes (z = 0, 1), which combine key structural elements of both of these catalysts. In particular, the incorporation of SNP heteroatoms into the ligand skeleton was found to be crucial for the design of a more product-selective catalyst in the synthesis of fluoral hemiacetals under kinetically controlled conditions. Based on experimental observations and computational analysis, this paper further extends the current state-of-the-art understanding of the accelerative role of KO-t-C4H9 in ester hydrogenation. It attempts to explain why a maximum turnover is seen to occur starting at 25 mol % base, in contrast to only 10 mol % with ketones as substrates.

SYNTHESIS OF FLUORO HEMIACETALS VIA TRANSITION METAL-CATALYZED FLUORO ESTER AND CARBOXAMIDE HYDROGENATION

This application is directed to use of transition metal-ligand complexes to hydrogenate fluorinated esters and carboxamides into fluorinated hemiacetals. Methods for synthesis of certain ligands are also provided.

PROCESS FOR PRODUCING A-FLUOROALDEHYDES

A production process of an α-fluoroaldehyde according to the present invention includes reaction of an α-fluoroester with hydrogen gas (H2) in the presence of a ruthenium complex. It is possible in the present invention to allow relatively easy industrial production of the α-fluoroaldehyde and to directly obtain, as stable synthetic equivalents of the α-fluoroaldehyde, not only a hydrate (as obtained by conventional techniques) but also a hemiacetal that is easy to purify and is of high value in synthetic applications. The present invention provides solutions to all problems in the conventional techniques and establishes the significantly useful process for production of the α-fluoroaldehyde.

Practical selective hydrogenation of α-fluorinated esters with bifunctional pincer-type ruthenium(II) catalysts leading to fluorinated alcohols or fluoral hemiacetals

Selective hydrogenation of fluorinated esters with pincer-type bifunctional catalysts RuHCl(CO)(dpa) 1a, trans-RuH2(CO)(dpa) 1b, and trans-RuCl2(CO)(dpa) 1c under mild conditions proceeds rapidly to give the corresponding fluorinated alcohols or hemiacetals in good to excellent yields. Under the optimized conditions, the hydrogenation of chiral (R)-2-fluoropropionate proceeds smoothly to give the corresponding chiral alcohol without any serious decrease of the ee value.