Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate

Base Information

• Chemical Name: Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate
• CAS No.: 164298-23-1
• Molecular Formula: C5H12F7N2P
• Molecular Weight: 264.13
• Hs Code.: 29252900
• European Community (EC) Number: 627-657-1
• Mol file: 164298-23-1.mol

Synonyms:tetramethylfluoroformamidinium hexafluorophosphate;TFFH cpd

Chemical Property of Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate

Chemical Property:

• Appearance/Colour: white crystals or crystalline powder
• Melting Point: 104-109 ºC
• PSA: 19.84000
• LogP: 3.52800
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 264.06263252
• Heavy Atom Count: 15
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

TFFH,Fluoro-N,N,N'',N''-tetramethylformamidiniumHexafluorophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)C(=[N+](C)C)F.F[P-](F)(F)(F)(F)F
• General Description: Fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate (TFFH) is a highly effective coupling reagent for the acylation of alcohols, thiols, and dithiocarbamates, offering superior reactivity, reduced byproduct formation, and lower toxicity compared to traditional reagents like DCC. It enables the efficient synthesis of esters, thioesters, and N-acyl-dithiocarbamates from carboxylic acids under mild conditions, with broad substrate compatibility, including sensitive functional groups. TFFH also facilitates chemoselective acylation, making it particularly useful for converting carboxylic acids to aldehydes, and is a versatile tool in organic synthesis due to its high yields and operational simplicity.

Refernces

TFFH as an excellent reagent for acylation of alcohols, thiols and dithiocarbamates

10.1055/s-2004-831250

The study presents an efficient method for synthesizing esters and thioesters from corresponding carboxylic acids using Tetramethylfluoroformamidinium hexafluorophosphate (TFFH) as a coupling reagent. The research details the preparation of N-acyl-dithiocarbamates from carboxylic acids and 1,3-thiazolidine-2-thione with TFFH. It highlights TFFH's advantages over traditional reagents like Dicyclohexylcarbodiimide (DCC), including higher reactivity, fewer byproducts, and lower toxicity. The study also demonstrates the chemoselective acylation of dithiocarbamates using TFFH, which is beneficial for preparing aldehydes from carboxylic acids. The results show that TFFH is effective for a wide range of substrates, including those with sensitive functional groups, and can be used under mild conditions with high yields, making it a valuable reagent in organic synthesis.