130408-89-8

Basic information

• Product Name: Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-3-yl)- (9CI)
• Synonyms: Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-3-yl)- (9CI);3-Trifluoroacetylpyrrole;2,2,2-Trifluoro-1-(1H-pyrrol-3-yl)-1-ethanone;2,2,2-trifluoro-1-(1H-pyrrol-3-yl)ethanone;3-(Trifluoroacetyl)-1H-pyrrole
• CAS NO: 130408-89-8
• Molecular Formula: C₆H₄F₃NO
• Molecular Weight: 163.0972696
• Product Categories: ACETYLHALIDE
• Mol File: 130408-89-8.mol

Chemical Properties

• Melting Point: 108-110 °C
• Boiling Point: 203.642 °C at 760 mmHg
• Flash Point: 76.96 °C
• Appearance: /
• Density: 1.41 g/cm³
• Storage Temp.: 2-8°C
• PKA: 14.30±0.50(Predicted)
• CAS DataBase Reference: Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-3-yl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-3-yl)- (9CI)(130408-89-8)
• EPA Substance Registry System: Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-3-yl)- (9CI)(130408-89-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 130408-89-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-3-yl)(9CI) is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of new molecules and materials with potential therapeutic and pesticidal properties.
Used in Medicinal Chemistry and Drug Development:
In the field of medicinal chemistry, Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-3-yl)(9CI) is employed as a building block for the development of new drugs. Its biological activity and potential therapeutic effects make it a promising candidate for further research and development.
Used in Research Applications:
Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-3-yl)(9CI) is also used in various research applications, where its unique properties and structure can be explored for the advancement of scientific knowledge and the development of innovative technologies.

Upstream product

• 109-97-7 pyrrole 
• 433-27-2 ethyl trifluoroacetaldehyde hemiacetal 
• 1336-21-6 ammonium hydroxide 
• 109317-75-1 4-trifluoroacetyl-2,3-dihydrofuran 
• 1013405-53-2 (E)-1,1,1-trifluoro-4-phenyl-4-ethoxy-2-(aminomethyl)-but-3-en-2-ol 
• 144219-77-2 1,1,1-trifluoro-4-(2,2-dimethoxyethylamino)-3-buten-2-one 
• 130408-88-7 3-(trifluoroacetyl)-1-(triisopropylsilyl)pyrrole 

Downstream Products

• 1255172-15-6 (S)-2,2,2-trifluoro-1-(1-(1-((4-methoxybenzyl)amino)but-3-en-2-yl)-1H-pyrrol-3-yl)ethanone 
• 1255172-17-8 (S)-1-(1-(1-(benzylamino)but-3-en-2-yl)-1H-pyrrol-3-yl)-2,2,2-trifluoroethanone 
• 144219-81-8 3-trifluoroacetyl-1-methylpyrrole 
• 144219-82-9 1-ethyl-3-trifluoroacetylpyrrole 

Relevant articles and documents

Mixed-Metal MIL-100(Sc,M) (M=Al, Cr, Fe) for Lewis acid catalysis and tandem C-C Bond formation and alcohol oxidation

The trivalent metal cations Al3+, Cr3+, and Fe3+ were each introduced, together with Sc3+, into MIL- 100(Sc,M) solid solutions (M=Al, Cr, Fe) by direct synthesis. The substitution has been confirmed by powder X-

Convenient one-pot synthesis of N-substituted 3-trifluoroacetyl pyrroles

A new one-pot strategy for the synthesis of a series of new N-substituted 3-trifluoroacetyl pyrroles is presented. These compounds were obtained by the reaction of 3-trifluoroacetyl-4,5-dihydrofuran with primary amines, which generated 1,1,1-trifluoro-3-(2-hydroxyethyl)-4-alkylaminobut-3-en-2-one intermediates. In most cases these intermediates were not stable enough to be isolated. Thus, in the same reaction vessel they were directly submitted to oxidation with PCC (Corey's reagent) to furnish 1,1,1-trifluoro-3-(2-ethanal)-4- alkylaminobut-3-en-2-ones, which under reflux underwent intramolecular cyclization to give the desired N-substituted 3-trifluoroacetyl pyrroles, in moderate yields. All of these pyrroles were tested against pan-susceptible Mycobacterium tuberculosis H37Rv and clinical isolates INH- and RMP-resistant strain and some of these compounds showed significant in vitro antimicrobial activity. Georg Thieme Verlag Stuttgart.

A new synthetic route to 3-polyfluoroalkyl-containing pyrroles

A novel approach to 3-polyfluoroalkyl pyrroles is reported based on step by step reactions: 1,2-addition of Me3SiCN to β-alkoxyvinyl polyfluoroalkyl ketones, reduction with LiAlH4 and subsequent hydrolysis with intramolecular cyclization. The hydrolytic instability of various polyfluoroalkyl groups at position 3 of the pyrrole ring was evident and a pathway for the hydrolysis was proposed.

A FACILE AND CONVENIENT SYNTHETIC METHOD FOR 3-TRIFLUOROACETYLPYRROLES

3-Trifluoroacetylpyrroles are easily obtained in excellent yields by oxygen-nitrogen exchange reaction of β-trifluoroacetylvinyl ethers with 2,2-dimethoxyethylamine and subsequent cyclodehydration of the products.

N-(Triisopropylsilyl)pyrrole. A Progenitor "Par Excellence" of 3-Substituted Pyrroles

A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the α positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the β position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields.Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the α positions is decelerated by a factor of >104, vs pyrrole at the same sites, without affecting reactivity at the β positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents.This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of β-substituted pyrroles, many of which would not be directly preparable from 1.TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions.This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound (5).