1547-87-1

Basic information

• Product Name: N,N-DIMETHYLTRIFLUOROACETAMIDE
• Synonyms: 2,2,2-Trifluoro-N,N-dimethylacetamide;TIMTEC-BB SBB008188;N,N-DIMETHYLTRIFLUOROACETAMIDE;2,2,2-TRIFLUORO-N,N-DIMETHYLACETAMIDE;Acetamide, 2,2,2-trifluoro-N,N-dimethyl-;N,N-diMethyltrifluoroacetaMaide
• CAS NO: 1547-87-1
• Molecular Formula: C₄H₆F₃NO
• Molecular Weight: 141.09
• Product Categories: Fine Chemical&Pharmaceutical
• Mol File: 1547-87-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 132 °C
• Flash Point: 36.7 °C
• Appearance: /
• Density: 1.23
• Vapor Pressure: 8.64mmHg at 25°C
• Refractive Index: 1.3610 to 1.3650
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -1?+-.0.70(Predicted)
• CAS DataBase Reference: N,N-DIMETHYLTRIFLUOROACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYLTRIFLUOROACETAMIDE(1547-87-1)
• EPA Substance Registry System: N,N-DIMETHYLTRIFLUOROACETAMIDE(1547-87-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 1993 3/PG III
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 1547-87-1(Hazardous Substances Data)

Usage

General Description

N,N-Dimethyltrifluoroacetamide, also known as DMF-TFA, is a highly polar and stable reagent commonly used in organic synthesis for the transformation of various functional groups. It is a colorless liquid with a strong and distinctive odor, and it is miscible with most organic solvents. DMF-TFA is often used as a strong polar aprotic solvent for reactions involving nucleophilic reagents, and it is also utilized as a reagent for the activation and protection of functional groups during organic synthesis. Additionally, it is used as a solvent for the isolation and purification of natural products, peptides, and other organic compounds. Despite its useful properties, DMF-TFA is highly toxic and should be handled with care, as exposure through inhalation, skin contact, or ingestion can lead to severe health effects.

InChI:InChI=1/C4H6F3NO/c1-8(2)3(9)4(5,6)7/h1-2H3

Upstream product

• 354-32-5 trifluoracetyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 383-63-1 ethyl trifluoroacetate, 
• 1608-26-0 Hexamethylphosphorous triamide 
• 506-59-2 N,N-dimethylammonium chloride 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 124-40-3 dimethyl amine 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 
• 56043-45-9 N,N,N',N'-tetramethylchlorformamidinium chloride 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 651-70-7 2,2,2-trifluoro-1-(thiophen-2-yl)ethan-1-one 
• 30933-31-4 2,2,2-trifluoro-1-(thiophen-3-yl)ethan-1-one 
• 75277-96-2 1-(benzofuran-2-yl)-2,2,2-trifluoroethan-1-one 
• 75277-97-3 1-(benzo[b]thiophen-2-yl)-2,2,2-trifluoroethan-1-one 
• 75277-99-5 3-hydroxymethyl-2-trifluoroacetyl benzothiophene 
• 75277-98-4 1-(3-Bromo-benzo[b]thiophen-2-yl)-2,2,2-trifluoro-ethanone 
• 188978-32-7 (4R,5S,6S,7R)-4,7-Dibenzyl-5,6-bis-(2-methoxy-ethoxymethoxy)-1,3-bis-[3-(2,2,2-trifluoro-acetyl)-benzyl]-[1,3]diazepan-2-one 
• 354-34-7 trifluoroacetyl fluoride 
• 432-00-8 bis(trifluoromethyl)carbamoyl fluoride 
• 1012330-13-0 1-(2-(3-(biphenyl-4-yl)-1-(tert-butyldimethylsilyloxy)propyl)oxazol-5-yl)-2,2,2-trifluoroethanone 
• 1261297-00-0 1-{3,3-dimethyl-2-[2-(trifluoromethyl)-1,3-dioxolan-2-yl]cyclobut-1-en-1-yl}-2,2,2-trifluoroethanone 
• 1261297-01-1 2,2,2-trifluoro-1-{7-[2-(trifluoromethyl)-1,3-dioxolan-2-yl]bicyclo[3.2.0]hept-6-en-6-yl}ethanone 
• 35472-34-5 1-(benzo[b]thiophen-3-yl)-2,2,2-trifluoroethan-1-one 
• 433-70-5 bistrifluoromethyl-trifluoroacetamide 

Relevant articles and documents

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Gas-phase NMR studies of N,N-dimethylthioamides. Influence of the thiocarbonyl substituent on the internal rotation activation energies

Temperature-dependent gas-phase 1H NMR spectra of seven thiocarbonyl-substituted N,N-dimethylthioamides (YCSN(CH3)2) obtained at 300 MHz are consistent with the following free activation energies ΔG?298 (kcal mol-1): Y = H, 22.5 (0.1); CH3, 18.0 (0.1); F, 18.3 (0.1); Cl, 16.9 (0.2); CF3, 17.2 (0.1); CH2CH3, 17.6 (0.1); CH(CH3)2, 16.3 (0.1). The results are compared to condensed-phase values and to the corresponding gas-phase oxoamides.

Amide bond formation in aqueous solution: Direct coupling of metal carboxylate salts with ammonium salts at room temperature

Herein, we report a green, expeditious, and practically simple protocol for direct coupling of carboxylate salts and ammonium salts under ACN/H2O conditions at room temperature without the addition of tertiary amine bases. The water-soluble coupling reagent EDC·HCl is a key component in the reaction. The reaction runs smoothly with unsubstituted/substituted ammonium salts and provides a clean product without column chromatography. Our reaction tolerates both carboxylate (which are unstable in other forms) and amine salts (which are unstable/volatile when present in free form). We believe that the reported method could be used as an alternative and suitable method at the laboratory and industrial scales. This journal is

Synthesis and reactivity of trifluorodithioacetates derived from trifluorothioacetamides

A general synthesis of trifluorodithioacetates is described by thiolysis of trifluorothioamidium salts, derived from trifluorothioacetamides. The reactivity of these CF3 bearing C2 building blocks has been investigated towards nucleophiles and in cycloaddition reactions. Trifluorodithioacetates react with dienes to give thiopyrans and with diazo compounds to give trifluoromethyl vinyl sulphides via thiirane intermediates. With amines, trifluorodithioacetates give rise to trifluorothioacetamides while thiols add by thiophilic attack leading to new trifluoroethane dithioacetal disulphide. Two equivalents of phosphite furnish one equivalent of thiophosphate and one of phosphorylated trifluoroethane.