111185-41-2

Basic information

• Product Name: 1H-Pyrrole, 2,5-dihydro-1-(trifluoroacetyl)- (9CI)
• Synonyms: 2,2,2-trifluoro-1-(3-pyrrolin-1-yl)ethanone;NSC340533;1H-Pyrrole, 2,5-dihydro-1-(trifluoroacetyl)- (9CI);N-Trifluoroacetyl-3-pyrroline;1-(2,5-dihydropyrrol-1-yl)-2,2,2-trifluoroethanone;1-(2,5-dihydropyrrol-1-yl)-2,2,2-trifluoro-ethanone
• CAS NO: 111185-41-2
• Molecular Formula: C₆H₆F₃NO
• Molecular Weight: 165.1131496
• Product Categories: ACETYLHALIDE
• Mol File: 111185-41-2.mol

Chemical Properties

• Boiling Point: 230.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.367±0.06 g/cm3(Predicted)
• PKA: -1.82±0.20(Predicted)
• CAS DataBase Reference: 1H-Pyrrole, 2,5-dihydro-1-(trifluoroacetyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole, 2,5-dihydro-1-(trifluoroacetyl)- (9CI)(111185-41-2)
• EPA Substance Registry System: 1H-Pyrrole, 2,5-dihydro-1-(trifluoroacetyl)- (9CI)(111185-41-2)

Safety Data

• Hazardous Substances Data: 111185-41-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrrole, 2,5-dihydro-1-(trifluoroacetyl)(9CI) is used as an intermediate in the synthesis of various organic compounds for the development of new pharmaceuticals. The trifluoroacetyl group in this compound provides a versatile building block for the creation of complex organic molecules, enabling the design and synthesis of novel drug candidates with potential therapeutic applications.
Used in Medicinal Chemistry:
1H-Pyrrole, 2,5-dihydro-1-(trifluoroacetyl)(9CI) is used as a key component in the design and synthesis of new drug candidates in medicinal chemistry. Its unique structure and functional groups allow for the development of innovative therapeutic agents with improved pharmacological properties, such as enhanced potency, selectivity, and bioavailability.
Used in Materials Science:
1H-Pyrrole, 2,5-dihydro-1-(trifluoroacetyl)(9CI) has potential applications in the field of materials science, where its unique chemical properties can be utilized to develop new materials with specific properties. The trifluoroacetyl group may contribute to the formation of novel materials with improved stability, reactivity, or other desirable characteristics for various applications.
Used in Organic Synthesis:
1H-Pyrrole, 2,5-dihydro-1-(trifluoroacetyl)(9CI) is used as a valuable building block in organic synthesis, enabling the preparation of a wide range of complex organic molecules. Its unique structure and functional groups facilitate the synthesis of diverse organic compounds, which can be further modified or functionalized to achieve specific properties or applications in various fields, such as pharmaceuticals, agrochemicals, or specialty chemicals.

Upstream product

• 73286-70-1 N-(tert-butoxycarbonyl)-3-pyrroline 
• 407-25-0 trifluoroacetic anhydride 
• 63468-63-3 2,5-dihydro-1H-pyrrole hydrochloride 
• 14618-49-6 N,N-diallyl trifluoroacetamide 
• 109-96-6 3-Pyrroline 

Downstream Products

• 164931-85-5 1-(6-oxa-3-azabicyclo[3.1.0]hexan-3-yl)-2,2,2-trifluoroethanone 
• 6442-87-1 2,2,2-trifluoro-1-pyrrolidin-1-ylethanone 
• 2803-00-1 N-trifluoroacetyl,N-benzyl piperazine 
• 1692-78-0 1-phenyl-4-trifluoroacetyl-piperazine 
• 3848-73-5 1-p-tolyl-4-trifluoroacetyl-piperazine 

Relevant articles and documents

Salicylaldimine ruthenium alkylidene complexes: Metathesis catalysts tuned for protic solvents

Tuning the electronic and steric environment of olefin metathesis catalysts with specialized ligands can adapt them to broader applications, including metathesis in aqueous solvents. Bidentate salicylaldimine ligands are known to stabilize ruthenium alkylidene complexes, as well as allow ringclosing metathesis in protic media. Here, we report the synthesis and characterization of exceptionally robust olefin metathesis catalysts bearing both bidentate salicylaldimine and N-heterocyclic carbene ligands, including a trimethylammonium-functionalized complex adapted for polar solvents. NMR spectroscopy and X-ray crystallographic analysis confirm the structures of the complexes. Although the N-heterocyclic carbene-salicylaldimine ligand combination limits the activity of these catalysts in non-polar solvents, this pairing enables efficient ring-closing metathesis of both dienes and enynes in methanol and methanol/water mixtures under air.

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An efficient method for ring-closing metathesis under solvent-free conditions and by microwave activation was esteblished. Non-thermal microwave specific effects were evident.

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Metathesis in water conducted by tailor-made encapsulated Grubbs' catalyst

Metathesis in water represents a current challenge in green chemistry, since hydrophobic catalysts are non-soluble in this medium. Although this issue has been addressed by modification of the hydrophobic ligand structure, alternative methods for conducting metathesis in water are of interest, such as catalyst encapsulation. In this contribution we report successful encapsulation of the Grubbs' second-generation catalyst in alginate hydrogels, representing a renewable resource, to perform ring-closing metathesis (RCM) in water. We initially investigated the influence of different solvents on the reaction rate and confirmed that water is a preferred solvent. A comparison of non-encapsulated and encapsulated catalyst in calcium alginate revealed that the reaction rate for non-encapsulated catalyst was notably higher, which can be explained by "on water" conditions in this case. Inside the beads the encapsulated catalyst remained heterogeneous, thus allowing to switch the catalysis mode between "in/on water" through encapsulation. To overcome diffusion limitation and enhance reaction rate, we prepared a tailor-made bead material by introducing hydrophobic octyl-grafted alginate amide. Using such a hydrogel, diffusion limitation was positively influenced by hydrophobisation of the matrix, resulting in up to quadrupled reaction rates compared to calcium alginate as a standard encapsulation material. In terms of recycling, this encapsulated catalyst revealed promising performance, retaining 80% of its activity after ten runs. This is the first reported application of hydrophobised alginate derivatives in catalysed organic synthesis, achieving excellent encapsulation efficiency, no measurable leaching and yields of up to 87%.

Room temperature ionic liquids: New solvents for Schrock's catalyst and removal using polydimethylsiloxane membranes

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Asymmetric Synthesis of cis -(S, R)-3-Amino-4-fluoro-1-methylpyrrolidine

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Olefin metathesis in air using latent ruthenium catalysts: Imidazole substituted amphiphilic hydrogenated ROMP polymers providing nano-sized reaction spaces in water

Imidazole substituted hydrogenated amphiphilic ROMP polymers were used as both surfactants and ligand precursors for olefin metathesis reactions in water. Amphiphilic ROMP polymers were synthesized using a two-step procedure. Firstly, dimethyl-5-norbornene-2,3-dicarboxylate was polymerized using ring-opening metathesis polymerization (ROMP)/cross-metathesis (CM) in the presence of allyl-PEG5000 methyl ether and a Grubbs 3rd generation (G3) catalyst. Secondly, a one-pot hydrogenation/aminolysis protocol was used for the post-polymerization modification of PEG end-capped polynorbornene derivatives. Hydrogenation reactions were carried out using residual G3 in the presence of formic acid/sodium formate in THF at 70 °C. The aminolysis reaction was carried out without isolation of the hydrogenated polymer, using triazabicyclodecene (TBD) and 1-(3-aminopropyl)-imidazole, forming imidazole substituted hydrogenated amphiphilic ROMP polymers (mod-Amph1) in an efficient manner. G1-mod-Amph1 formed micelle structures in water with an average particle size of 85.95 (±35) nm as determined by transmission electron microscopy (TEM) and dynamic light scattering (DLS) analysis. The diffusion of Grubbs 1st generation (G1) catalyst into the micelle structure has led to the formation of nano-sized catalysts which exhibited a latent characteristic. The diffusion of hydrophobic olefinic substrates into the nano-reaction spaces, followed by activation of the catalyst with HCl led to a very efficient catalytic system for ring-closing metathesis reactions. RCM reactions of various hydrophobic dienes can run in non-degassed water under an air atmosphere. The catalyst system exhibits similar performance under an air atmosphere even in tap water, reaching a conversion value of 90% for RCM of diethyl diallylmalonate with a catalytic loading of 1% Ru.

N-Heterocyclic Carbene Complexes Of Metal Imido Alkylidenes And Metal OXO Alkylidenes, And The Use Of Same

The invention relates to an N-heterocyclic carbene complex of general formulas I to IV (I) (II) (III) (IV), according to which A1 stands for NR2 or PR2, A2 stands for CR2 R2′, NR2, PR2, 0 or S, A3 stands for N or P, and C stands for a carbene carbon atom, ring B is an unsubstituted or a mono or poly-substituted 5 to 7-membered ring, substituents R2 and R2′ stand, inter alia, for a linear or branched C1-Cw-alkyl group and, if N and N each stand for NR2 or PR2, are the same or different, M in formulas I, II, III or IV stands for Cr, Mo or W, X 1 or X2 in formulas I to IV are the same or different and represent, inter alia, C1-C1s carboxylates and C1-C1s-alkoxides, Y is inter alia oxygen or sulphur, Z is inter alia a linear or branched C1-Cw-alkylenoxy group, and R 1 and R1′ in formulas I to IV are, inter alia, an aliphatic or aromatic group. These compounds are particularly suitable for use as catalysts for olefin metathesis reactions and have the advantage, compared to known Schrock carbene complexes, of displaying clearly increased tolerance to functional groups such as, in particular, aldehydes, secondary amines, nitriles, carboxylic acids and alcohols.