1546-79-8

Basic information

• Product Name: 1-(Trifluoroacetyl)imidazole
• Synonyms: 1H-Imidazole, 1-(trifluoroacetyl)-;N-TRIFLUOROACETYLIMIDAZOLE;TRIFLUOROACETYLIMIDAZOLE;TFAI;1-(trifluoroacetyl)-1h-imidazole;1-(TRIFLUOROACETYL)IMIDAZOLE;1-(TRIFLUOROACETYL)IMIDAZOLE, DERIVATI-Z ATION REAGENT;1-(TRIFLUOROACETYL)IMIDAZOLE, DERIVATIZA TION GRADE
• CAS NO: 1546-79-8
• Molecular Formula: C₅H₃F₃N₂O
• Molecular Weight: 164.09
• EINECS: 216-282-5
• Product Categories: ACETYLHALIDE;Imidazol&Benzimidazole;Heterocyclic Compounds;Acylation (GC Derivatizing Reagents);Analytical Chemistry;GC Derivatizing Reagents;Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Building Blocks;Acylation ReagentsBuilding Blocks;Analytical/Chromatography;Derivatization Reagents;Heterocyclic Building Blocks;Imidazoles;Acylation Reagent
• Mol File: 1546-79-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 137 °C(lit.)
• Flash Point: 113 °F
• Appearance: colorless to pink liquid
• Density: 1.442 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.424(lit.)
• Storage Temp.: 0-6°C
• PKA: 0.78±0.10(Predicted)
• Water Solubility: reacts
• Sensitive: Moisture Sensitive
• BRN: 608904
• CAS DataBase Reference: 1-(Trifluoroacetyl)imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(Trifluoroacetyl)imidazole(1546-79-8)
• EPA Substance Registry System: 1-(Trifluoroacetyl)imidazole(1546-79-8)

Safety Data

• Hazard Codes: Xi,F,C
• Statements: 10-36/37/38-34-22
• Safety Statements: 26-36/37-45-36/37/39-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1546-79-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to pink liquid

Uses

1-(Trifluoroacetyl)imidazole was used as a derivating agent to sequentially derivatize functional groups like amino groups, in a study demonstrating trimethylsilyl esters of aromatic and aliphatic sulfonic acids.

General Description

1-(Trifluoroacetyl)imidazole is a derivatizing reagent.

InChI:InChI=1/3FH.Fe.3H2O/h3*1H;;3*1H2/q;;;+3;;;/p-3

Upstream product

• 288-32-4 1H-imidazole 
• 407-25-0 trifluoroacetic anhydride 
• 530-62-1 1,1'-carbonyldiimidazole 
• 76-05-1 trifluoroacetic acid 
• 130451-27-3 C₄F₆O₂S 
• 18156-74-6 1-(Trimethylsilyl)imidazole 

Downstream Products

• 18087-60-0 2,2,2-trifluoro-1-(5-methylfuran-2-yl)ethanone 
• 18931-61-8 4,4,4-trifluoro-1-(4-bromophenyl)butane-1,3-dione 
• 950908-40-4 2-trifluoroacetyl-5-methylcyclohexane-1,3-dione 
• 950908-42-6 2-trifluoroacetyl-5-phenylcyclohexane-1,3-dione 
• 950908-43-7 2-trifluoroacetyl-5-(4-methoxyphenyl)cyclohexane-1,3-dione 
• 950908-41-5 2-trifluoroacetyl-4-carbomethoxy-5,5-dimethylcyclohexane-1,3-dione 
• 950908-39-1 2-(2,2,2-trifluoroacetyl)cyclohexane-1,3-dione 
• 893842-26-7 5,5-dimethyl-2-(2,2,2-trifluoroacetyl)cyclohexane-1,3-dione 
• 1076195-14-6 4,4,4-trifluoro-1-(4-methoxyphenyl)-2-methyl-1,3-butanedione 
• 322-06-5 4,4,4-trifluoro-2-methyl-1-phenyl-1,3-butanedione 
• 343564-34-1 1-(4-tert-butyldimethylsilyloxy)-3-chlorophenyl-4,4,4-trifluoro-1,3-butanedione 
• 343564-46-5 2-fluoro-4-(4,4,4-trifluoro-3-oxobutanoyl)phenyltrifluoromethanesulfonate 
• 343564-26-1 1-(4-bromophenyl)-2,4,4,4-tetrafluoro-1,3-butanedione 
• 343564-58-9 5-(5-(4-Bromo-3-fluorophenyl)-4-ethyl-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide 

Relevant articles and documents

Preparative synthesis of 2,2-dimethyl-5-(trifluoroacetyl)-1,3-dioxane-4,6-dione (2-trifluoroacetyl Meldrum's acid) and 2,2-dimethyl-6-(trifluoromethyl)-4H-1,3-dioxin-4-one and their synthetic usefulness as (trifluoroacetyl)ketene precursors

A simple and reliable method for the preparation of 2,2-dimethyl-5-(trifluoroacetyl)-1,3-dioxane-4,6-dione and 2,2-dimethyl-6-(trifluoromethyl)-4H-1,3-dioxin-4-one on a multigram scale was developed. These (trifluoroacetyl)ketene precursors were used in the hetero-Diels-Alder reaction with dialkylcyanamides and 1-ethoxyprop-1-yne, as well as in some reactions with nucleophiles.

EFFICIENT OXYGENATION OF THIOPHOSPHORYL AND SELENOPHOSPHORYL GROUPS USING TRIFLUOROACETIC ANHYDRIDE

Trifluoroacetic anhydride reacts with organophosphorus compounds containing thiophosphoryl and selenophosphoryl groups converting them in high yield to the corresponding oxygenated systems.