Perfluorobutanesulfonyl fluoride information

Perfluorobutanesulfonyl fluoride

Names
Preferred IUPAC name 1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl fluoride
Identifiers
CAS Number	375-72-4
3D model (JSmol)	Interactive image
Abbreviations	NfF
ChemSpider	61131
ECHA InfoCard	100.006.175
EC Number	206-792-6
PubChem CID	67814
UNII	WC4FPA9BCM Y
CompTox Dashboard (EPA)	DTXSID20861913
InChI InChI=1S/C4F10O2S/c5-1(6,3(9,10)11)2(7,8)4(12,13)17(14,15)16 Key: LUYQYZLEHLTPBH-UHFFFAOYSA-N InChI=1/C4F10O2S/c5-1(6,3(9,10)11)2(7,8)4(12,13)17(14,15)16 Key: LUYQYZLEHLTPBH-UHFFFAOYAE
SMILES C(C(C(F)(F)S(=O)(=O)F)(F)F)(C(F)(F)F)(F)F
Properties
Chemical formula	C4F10O2S
Molar mass	302.09 g/mol
Density	1.682 g/mL[1]
Melting point	< −120 °C (−184 °F; 153 K)
Boiling point	65 to 66 °C (149 to 151 °F; 338 to 339 K)[2]
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Perfluorobutanesulfonyl fluoride (nonafluorobutanesulfonyl fluoride, NfF) is a colorless, volatile liquid that is immiscible with water but soluble in common organic solvents. It is prepared by the electrochemical fluorination of sulfolane. NfF serves as an entry point to nonafluorobutanesulfonates (nonaflates), which are valuable as electrophiles in palladium catalyzed cross coupling reactions. As a perfluoroalkylsulfonylating agent, NfF offers the advantages of lower cost and greater stability over the more frequently used triflic anhydride. The fluoride leaving group is readily substituted by nucleophiles such as amines, phenoxides, and enolates, giving sulfonamides, aryl nonaflates, and alkenyl nonaflates, respectively. However, it is not attacked by water (in which it is stable at pH<12). Hydrolysis by barium hydroxide gives Ba(ONf)₂, which upon treatment with sulfuric acid gives perfluorobutanesulfonic acid and insoluble barium sulfate.