407-24-9

Basic information

• Product Name: BISTRIFLUOROACETAMIDE
• Synonyms: Diacetamide, 2,2,2,2',2',2'-hexafluoro-;BTFA;BISTRIFLUOROACETAMIDE;2,2,2-trifluoro-N-(trifluoroacetyl)acetamide;Bis(trifluoroacetyl)amine;2,2,2-trifluoro-N-(2,2,2-trifluoroacetyl)acetamide
• CAS NO: 407-24-9
• Molecular Formula: C₄HF₆NO₂
• Molecular Weight: 209.05
• EINECS: 206-981-3
• Product Categories: Acylation (GC Derivatizing Reagents);Analytical Chemistry;GC Derivatizing Reagents
• Mol File: 407-24-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 80-86 °C
• Boiling Point: 120 °C / 1mmHg
• Flash Point: 7.7°C
• Appearance: /
• Density: 1.603g/cm³
• Vapor Pressure: 59.4mmHg at 25°C
• Refractive Index: 1.31
• Solubility: almost transparency in hot Toluene
• BRN: 1793118
• CAS DataBase Reference: BISTRIFLUOROACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BISTRIFLUOROACETAMIDE(407-24-9)
• EPA Substance Registry System: BISTRIFLUOROACETAMIDE(407-24-9)

Safety Data

• Hazard Codes: C
• Statements: 36/37/38-36/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 3-10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 407-24-9(Hazardous Substances Data)

Usage

Purification Methods

A major impurity is trifluoroacetamide. Add trifluoroacetic anhydride to BTFA, reflux for 2hours and fractionate using a Vigreux column (p 11) at atmospheric pressure. [Donike J Chromatogr 78 273 1973, Beilstein 2 IV 471.]

InChI:InChI=1/C4HF6NO2/c5-3(6,7)1(12)11-2(13)4(8,9)10/h(H,11,12,13)

Upstream product

• 2207-50-3 2-amino-5-phenyl-2-oxazoline 
• 407-25-0 trifluoroacetic anhydride 
• 354-38-1 2,2,2-trifluoroacetamide 
• 60956-76-5 3,3,3-trifluoro-1-oxo-1-propene-2-sulfonyl fluoride 
• 14565-32-3 2,2,2-trifluoroacetyl isocyanate 
• 2925-25-9 trifluorothioacetic acid 
• 556-64-9 methyl thiocyanate 
• 76-05-1 trifluoroacetic acid 
• 616-05-7 2-bromohexanoic acid 
• 353-85-5 trifluoroacetonitrile 

Downstream Products

• 354-34-7 trifluoroacetyl fluoride 
• 460-49-1 trifluoromethyl isocyanate 
• 354-38-1 2,2,2-trifluoroacetamide 
• 2561-21-9 n-octyl trifluoroacetate 
• 331-04-4 2,2,2-trifluoro-N-(1-methyl-2-phenylethyl)acetamide 

Relevant articles and documents

Preparation of fluorinated imides

A direct method for the preparation of trifluoroacetimides has been extended to the preparation of trifluoroacetyl trifluoracetimide and the new compound trifluoromethylsulfuryl trifluoroacetimide. Points concerning previously reported syntheses of trifluoroacetyl isocyanate have also been clarified.

TRIFLUOROACETIC ACID IN THE SYNTHESIS OF THIOLCARBAMATES AND S-METHYL ALKANETHIOATES

The major products of the reaction of 2-bromohexanoic acid with methyl thiocyanate in trifluoroacetic acid are S-methyl 2-bromohexanethioate (II) (55percent yield), S-methyl 2,2,2-trifluoroethanethioate (IV) (31percent yield), N-trifluoroacetyltrifluoroacetamide (V) (11percent yield), and N-trifluoroacetyl-S-methylthiolcarbamate (III) (29percent yield).N-2-Bromohexanoyl-S-methylthiolcarbamate (I), N-2-bromohexanoyltrifluoroacetamide (VI), 2-thiapropioamide (VII), and S-methyl hexanethioate (VIII) are also formed in minor amounts.

Trifluoroacetylation and Subsequent Pyrolysis of 2-Amino-2-oxazolines

Treatment of 2-amino-5-phenyl-2-oxazoline (I) with trifluoroacetic anhydride gave 1,3-bis(2,2,2-trifluoroacetyl)-1-urea (II).Compound II was pyrolyzed at 120 deg C to give 2,2,2-trifluoroacetyl isocyanate (III) and 2,2,2-trifluoro-N-acetamide (IV).Compound II was readily hydrolyzed to give 1-(2,2,2-trifluoroacetyl)-3-urea (VI).Compound VI was pyrolyzed at 230 deg C to give 2,2,2-trifluoroacetamide (VII) and 2,2,2-trifluoro-N-(E)-styrylacetamide (VIII).It was considered that the formation of VIII proceeded through the intermediate 2-(2,2,2-trifluoroacetyloxy)-2-phenylethyl isocyanate (XI) or 1-(2,2,2-trifluoroacetyl)-3-(E)-styrylurea (XII), as shown in Chart 1.Keywords - 2-amino-2-oxazoline; trifluoroacetylation; pyrolysis; 1,3-bis(2,2,2-trifluoroacetyl)-1-alkylurea; O,N-bis(2,2,2-trifluoroacetyl)aminoethanol; 1-(2,2,2-trifluoroacetyl)-3-alkylurea; 1-(2,2,2-trifluoroacetyl)-3-alkenylurea