38986-89-9

Basic information

• Product Name: 2-Propenoyl fluoride, 3-phenyl-, (E)-
• CAS NO: 38986-89-9
• Molecular Formula: C9H7FO
• Molecular Weight: 150.152
• Mol File: 38986-89-9.mol
• Article Data: 29

Chemical Properties

• CAS DataBase Reference: 2-Propenoyl fluoride, 3-phenyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoyl fluoride, 3-phenyl-, (E)-(38986-89-9)
• EPA Substance Registry System: 2-Propenoyl fluoride, 3-phenyl-, (E)-(38986-89-9)

Safety Data

• Hazardous Substances Data: 38986-89-9(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 146691-82-9 1,3-dibromo-1,1-difluoro-3-phenylpropane 
• 103-64-0 bromostyrene 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 102-92-1 cinnamoyl chloride 
• 14371-10-9 (E)-3-phenylpropenal 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-92-1 Cinnamoyl chloride 
• 1257324-44-9 4-methoxybenzyl cinnamate 
• 538-56-7 cinnamic acid anhydride 
• 621-82-9 Cinnamic acid 

Downstream Products

• 19202-21-2 1-trans-cinnamoylpyrrolidine 
• 103-41-3 (E)-cinnamic acid benzyl ester 
• 143167-61-7 (R)-4-benzyl-3-cinnamoyloxazolidin-2-one 
• 1279102-70-3 6,8-diphenyl-1,2,3,4,5,6-hexahydronaphthalene 
• 1353087-96-3 C₂₂H₂₁⁽²⁾H 
• 1279102-73-6 8-isopropyl-6-phenyl-1,2,3,4,5,6-hexahydronaphthalene 
• 1279102-89-4 7-deutero-6,8-diphenyl-1,2,3,4,5,6-hexahydronaphthalene 

Relevant articles and documents

Rapid and column-free syntheses of acyl fluorides and peptides usingex situgenerated thionyl fluoride

Thionyl fluoride (SOF2) was first isolated in 1896, but there have been less than 10 subsequent reports of its use as a reagent for organic synthesis. This is partly due to a lack of facile, lab-scale methods for its generation. Herein we report a novel protocol for theex situgeneration of SOF2and subsequent demonstration of its ability to access both aliphatic and aromatic acyl fluorides in 55-98% isolated yields under mild conditions and short reaction times. We further demonstrate its aptitude in amino acid couplings, with a one-pot, column-free strategy that affords the corresponding dipeptides in 65-97% isolated yields with minimal to no epimerization. The broad scope allows for a wide range of protecting groups and both natural and unnatural amino acids. Finally, we demonstrated that this new method can be used in sequential liquid phase peptide synthesis (LPPS) to afford tri-, tetra-, penta-, and decapeptides in 14-88% yields without the need for column chromatography. We also demonstrated that this new method is amenable to solid phase peptide synthesis (SPPS), affording di- and pentapeptides in 80-98% yields.

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.

Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles

A series of acyl fluorides was synthesized at 100 mmol scale using phase-transfer-catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at room temperature, followed by extraction and distillation. Isolated acyl fluorides (usually 7-20 g) display excellent purity and can be transformed into sterically hindered amides and esters when treated with lithium amide bases and alkoxides under mild conditions.