461-53-0

Usage

InChI:InChI=1/C4H7FO/c1-2-3-4(5)6/h2-3H2,1H3

Upstream product

• 106-31-0 butanoic acid anhydride 
• 98-88-4 benzoyl chloride 
• 107-92-6 butyric acid 
• 141-75-3 butyryl chloride 
• 357-83-5 N-(2-chloro-1,1,2-trifluoroethyl)diethylamine 
• 455-32-3 benzoyl fluoride 
• 79-30-1 isobutyryl chloride 

Downstream Products

• 495-40-9 propiophenone 
• 623-42-7 butanoic acid methyl ester 
• 109-21-7 butyl butyrate 
• 335-42-2 perfluorobutyryl fluoride 

Relevant academic research and scientific papers

Large-Scale Preparation of N-Butanoyl- l -glutathione (C4-GSH)

A novel two-step synthesis of N-butanoyl-l-glutathione (C4-GSH) was developed involving the chemical modification of the commercially available starting material l-glutathione (GSH). This process not only has the advantage of selective acylation of the GSH amino group without the use of previous solid-phase organic synthesis and/or protecting group chemistry but also highlights the use of inexpensive reagents such as butyric anhydride and sodium methoxide as well as environmentally acceptable solvents such as water and methanol. This chromatography- and salt-free synthesis of C4-GSH is cost-effective, safe, efficient, and easy to scale up.

METHOD AND REAGENT FOR DEOXYFLUORINATION

A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.

Deoxyfluorination of Carboxylic Acids with KF and Highly Electron-Deficient Fluoroarenes

A deoxyfluorination reaction of carboxylic acids using potassium fluoride (KF) and highly electron-deficient fluoroarenes is reported here, giving acyl fluorides in moderate to excellent yield (57-92% based on NMR integration and 34-95% for isolated examples).

C-F Bond Activation of a Perfluorinated Ligand Leading to Nucleophilic Fluorination of an Organic Electrophile

We report a fluorine transfer reaction in which fluorine from a perfluorinated ligand undergoes C-F bond activation and transfers to an electrophile, resulting in the formation of a new fluorinated product and dimerization of the monodefluorinated complex. Treatment of [(η5,κ2C-C5Me4CH2C6F5CH2NC3H2NMe)-RhCl] with the organic electrophile, toluoyl chloride, resulted in the formation of a rhodium(III) metallocycle via C-F bond activation assisted defluorinative coupling. Fission of the C-F bond liberated nucleophilic fluoride, which converted acyl chloride to acyl fluoride. The overall reaction was monitored using a multivariate analysis approach in real time.

Homogeneous catalytic hydrogenation of perfluoro methyl esters

The first example of perfluoroalkyl methyl ester RfC(O)OMe (Rf = C3F7, C5F11) reduction by homogeneous catalytic hydrogenation with the ruthenium catalyst Ru-MACHO is herein reported. The hydrogenation process leads to the corresponding perfluorinated alcohols thus replacing sodium borohydride that has so far represented the state of art in perfluoro ester reduction.

Detection of Elusive Chloro- and Bromo Substituted Ozonides by Nucleophilic Substitution Reactions

Ozonolyses of 2,3-dichloro-2-butene (4), 4,5-dichloro-4-octene (9) and 2,3-dibromo-1,4-dichloro-2-butene (12) on polyethylene gave the corresponding ozonides 5,10 and 13a, respectively, which could not be isolated or unequivocally identified. Their identity could be proven, however, via substitution of the chloro- or bromo substituents at the ozonide rings by stabilizing substituents and subsequent isolation of the substituted ozonides 6, 11, 13b and 13c. Ozonolysis of 2,3-diacetoxy-2-butene (14) on polyethylene, in dichloro methane and in pentane gave mixtures of 16 and 17 but not ozonide 6.

Halogen Mobility in SN2 Reactions of Carbonyl Compounds. Comparisons with Aromatic Halogen Mobility

Kinetic studies, using conductometric techniques, have been carried out for isopropanolysis (solvolysis) reactions of some alkanoyl, benzoyl and perfuoroalkanoyl halides, viz. butanoyl and benzoyl fluorides, chlorides,and bromides and perfluoropentanoyl fluoride and chloride.The halogen mobility orders, F N reactions at saturated and aromatic carbon, and have been discussed in mechanistic terms.The substrate class reactivity order is perfluoroalkanoyl >> benzoyl, alkanoyl.The actual ratios depend on which halogen is displaced, the ratios being larger on displacement of fluorine.

THE ELECTROCHEMICAL FLUORINATION OF ORGANIC COMPOUNDS: FURTHER DATA IN SUPPORT OF THE ECbECN MECHANISM

Data in support of the four-stage mechanism ECbECN result from the electrochemical fluorination of some acyl halides (benzoyl, n-butyryl and iso-butyryl, benzenesulphonyl and p-toluenesulphonyl chlorides) and amines (tripropylamine and N-methylmorpholine).

ENHANCED EFFECT OF SPRAY-DRIED POTASSIUM FLUORIDE ON FLUORINATION

Spray-dried potassium fluoride was found to be much less hygroscopic and much more effective as a fluorinating agent than usual calcine-dried potassium fluoride.Organic compounds containing an activated halogen atom were readily fluorinated in acetonitrile with spray-dried potassium fluoride.