55039-89-9

Basic information

• Product Name: 2,2-DIFLUOROPENT-4-ENOIC ACID
• Synonyms: 2,2-DIFLUOROPENT-4-ENOIC ACID;4-Pentenoic acid, 2,2-difluoro-
• CAS NO: 55039-89-9
• Molecular Formula: C₅H₆F₂O₂
• Molecular Weight: 136.1
• Mol File: 55039-89-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 56-58°C/3mm
• Flash Point: 55℃
• Appearance: /
• Density: 1.218
• Storage Temp.: 2-8°C
• PKA: 1.27±0.10(Predicted)
• Water Solubility: Immiscible with water.
• CAS DataBase Reference: 2,2-DIFLUOROPENT-4-ENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIFLUOROPENT-4-ENOIC ACID(55039-89-9)
• EPA Substance Registry System: 2,2-DIFLUOROPENT-4-ENOIC ACID(55039-89-9)

Safety Data

• Hazard Codes: Xi
• RIDADR: 3265
• HazardClass: IRRITANT
• PackingGroup: Ⅱ
• Hazardous Substances Data: 55039-89-9(Hazardous Substances Data)

Usage

Description

2,2-Difluoropentan-4-enoic acid is an organic compound characterized by the presence of two fluorine atoms at the second carbon position and a double bond between the fourth and fifth carbon atoms. It is a key intermediate in the synthesis of various pharmaceutical compounds and has potential applications in the chemical and pharmaceutical industries.

Uses

Used in Pharmaceutical Industry:
2,2-Difluoropentan-4-enoic acid is used as a key intermediate for the synthesis of 5-hydroxy-3,3-difluoropiperidine, which is a compound with potential pharmaceutical applications. It is involved in the iodolactonization reaction to give the corresponding gamma-lactone, which is then converted to prepare the desired piperidine derivative.

Upstream product

• 116-14-3 polytetrafluoroethylene 
• 107-18-6 allyl alcohol 
• 113991-42-7 1,2,2-trifluorovinyl allyl ether 
• 118373-18-5 trimethylsilyl 2,2-difluoro-4-pentenoate 
• 118337-48-7 allyl chlorodifluoroacetate 

Downstream Products

• 110482-96-7 2,2-difluoro-4-pentenoic acid ethyl ester 
• 364049-82-1 N-(4-methoxyphenyl)-1-chloro-2,2-difluoro-4-pentenimidoyl chloride 
• 911395-26-1 C₁₃H₁₄ClF₂N 
• 577748-50-6 C₁₂H₁₂ClF₂NO 
• 1397264-55-9 ethyl [4,4-difluoro-1-(4-methoxyphenyl)-5-oxopyrrolidin-2-yl]acetate 
• 1397264-79-7 ethyl (2E)-5,5-difluoro-6-[(4-methoxyphenyl)amino]-6-oxohex-2-enoate 
• 1397264-53-7 2,2-difluoro-N-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]pent-4-enamide 
• 1799733-46-2 3-chloro-2-(1,1-difluorobut-3-en-1-yl)-6-methoxyquinoxaline 
• 1535212-06-6 C₃₁H₄₀F₂N₄O₇ 
• 189136-13-8 5-(azidomethyl)-3,3-difluorodihydrofuran-2(3H)-one 
• 911395-45-4 (-)-2-(trimethylsilyl)ethyl (2S)-3,3-difluoro-2-(2-t-butoxycarbonylallyl)-2-{[(1R)-1-phenyl-2-methoxyethyl]amino}-5-hexenoate 
• 911395-46-5 (-)-2-(trimethylsilyl)ethyl (2S)-3,3-difluoro-2-{[(1R)-1-phenyl-2-methoxyethyl]amino}-2-(2-phenylallyl)-5-hexenoate 
• 911395-43-2 (-)-2-(trimethylsilyl)ethyl (2S)-3,3-difluoro-2-{[(1R)-1-phenyl-2-methoxyethyl]amino}-(2-methylallyl)-5-hexenoate 
• 911395-44-3 (-)-2-(trimethylsilyl)ethyl (2S)-3,3-difluoro-2-(1,1-dimethylallyl)-2-{[(1R)-1-phenyl-2-methoxyethyl]amino}-5-hexenoate 

Relevant articles and documents

Practical preparation of 3,3-difluoropyrrolidine

A practical and cost-effective synthesis of 3,3-difluoropyrrolidine is reported. The synthesis involves the isolation of two intermediates, which are prepared via two efficient through processes: (1) a Claisen rearrangement followed by a Ru(VIII)-catalyzed oxidation to prepare the 2,2-difluorosuccinic acid and (2) an efficient cyclization to form N-benzyl-3,3-difluoropyrrolidinone followed by BH3·Me2S reduction.

Fluorinated analogues as mechanistic probes in valproic acid hepatotoxicity: Hepatic microvesicular steatosis and glutathione status

It is postulated that the hepatotoxicity of valproic acid (VPA) results from the mitochondrial β-oxidation of its cytochrome P450 metabolite, 2- propyl-4-pentenoic acid (4-ene VPA), to 2-propyl-(E)-2,4-pentadienoic acid ((E)-2,4-diene VPA) which, in the CoA thioester form, either depletes GSH or produces a putative inhibitor of β-oxidation enzymes. In order to test this hypothesis, 2-fluoro-2-propyl-4-pentenoic acid (α-fluoro-4-ene VPA) which was expected to be inert to β-oxidative metabolism was synthesized and its effect on rat liver studied in comparison with that of 4-ene VPA. Similarly, the known hepatotoxicant 4-pentenoic acid (4-PA) and 2,2-difluoro-4-pentenoic acid (F2-4-PA) were compared. Male Sprague-Dawley rats (150-180 g, 4 rats per group) were dosed ip with 4-one VPA (0.7 mmol/kg per day), 4-PA (1.0 mmol/kg per day), or equivalent amounts of their α-fluorinated analogues for 5 days. Both 4-ene VPA and 4-PA induced severe hepatic microvesicular steatosis (> 85% affected hepatocytes), and 4-ene VPA produced mitochondrial alterations. By contrast, α-fluoro-4-ene VPA and F2-4-PA were not observed to cause morphological changes in the liver. The major metabolite of 4-ene VPA in the rat urine and serum was the β-oxidation product (E)-2,4-diene VPA. The N-acetylcysteine (NAC) conjugate of (E)-2,4-diene VPA was also found in the urine. Neither (E)-2,4-diene VPA nor the NAC conjugate could be detected in the rats administered α-fluoro-4-ene VPA. In a second set of rats (3 rats per group), total liver GSH levels were determined to be depleted to 56% and 72% of control following doses of 4-ene VPA (1.4 mmol/kg) and equivalent α-fluoro-4-ene VPA, respectively. Mitochondrial GSH remained unchanged in the α-fluoro-4-ene VPA treated group but was reduced to 68% of control in the rats administered 4-ene VPA. These results strongly support the theory that hepatotoxicity of 4-ene VPA, and possibly VPA itself, is mediated largely through β-oxidation of 4-ene VPA to reactive intermediates that are capable of depleting mitochondrial GSH.

FLUORINE-CONTAINING ORGANOZINC REAGENTS. V. THE REFORMATSKII-CLAISEN REACTION OF CHLORODIFLUOROACETIC ACID DERIVATIVES

Silicon induced Reformatskii-Claisen reaction of allyl chlorodifluoroacetate (1) affords 2,2-difluoro-4-pentenoic acid (2) in good yields.Starting from inexpensive chlorodifluoroacetic acid, a variety of useful fluorine-containing synthetic building block