Nonafluorobutanesulfonyl fluoride

Nonafluorobutanesulfonyl fluoride Basic information
Product Name:Nonafluorobutanesulfonyl fluoride
Synonyms:Nonafluorobutanesulfonyl fluoride, 90+%;Nonafluorobutanesulphonyl fluoride, tech. 90%;1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonic acid fluoride;Nonafluoro-1-butanesulfonic acid fluoride;Perfluoro-1-butanesulfonyl fluoride,92%;1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonylf;Perfluorobutanesulphonyl fluoride 95%;Perfluorobutyl fluoride
CAS:375-72-4
MF:C4F10O2S
MW:302.09
EINECS:206-792-6
Product Categories:Fine chemical;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry;bc0001
Mol File:375-72-4.mol
Nonafluorobutanesulfonyl fluoride Structure
Nonafluorobutanesulfonyl fluoride Chemical Properties
Melting point -110°C
Boiling point 64 °C (lit.)
density 1.682 g/mL at 25 °C (lit.)
vapor pressure 16.665kPa at 20℃
refractive index n20/D 1.3(lit.)
Fp 65-66°C
storage temp. Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility Chloroform (Sparingly), Methanol (Sparingly)
form Liquid
color Colorless to yellow
Specific Gravity1.682
Water Solubility Hydrolyses in water.
Sensitive Moisture Sensitive
BRN 1813589
Stability:Hygroscopic
InChIKeyLUYQYZLEHLTPBH-UHFFFAOYSA-N
CAS DataBase Reference375-72-4(CAS DataBase Reference)
NIST Chemistry ReferenceNonafluorobutanesulfonyl fluoride(375-72-4)
EPA Substance Registry System1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4-nonafluoro- (375-72-4)
Safety Information
Hazard Codes C
Risk Statements 34
Safety Statements 26-36/37/39-45-25
RIDADR UN 3265 8/PG 2
WGK Germany 3
10-21
Hazard Note Corrosive
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29049090
MSDS Information
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Nonafluorobutanesulfonyl fluoride Usage And Synthesis
Description1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl fluoride (NfF) also called Nonafluorobutanesulfonyl fluoride is a versatile compound in organic synthesis. It can be used as a fluoride source for the nucleophilic introduction of fluorine, but it is also frequently applied as sulfonylation reagent generating intermediates with strong electron withdrawing perfluorinated alkyl substituents.
Chemical PropertiesNonafluorobutanesulfonyl fluoride 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.
UsesBenzynes were generated from o-(trimethylsilyl) phenols using nonafluorobutanesulfonyl fluoride (NfF) by a domino process.Nonafluorobutanesulfonyl fluoride (nonaflyl fluoride, C 4 F 9 SO 2 F, NfF) is the most widely used commercially available reagent for the synthesis of nonaflates.
ApplicationPerfluoro-1-butanesulfonyl fluoride (NfF) reacts with alcohols, including phenols, to yield nonafluorobutanesulfonate esters (nonaflates). Nonaflates can be used as electrophiles in several palladium-catalyzed cross coupling reactions and in Buchwald-Hartwig amination. NfF can also be used to prepare aryl nonaflates by reacting with corresponding aryloxysilanes in the presence of fluoride ion.
SynthesisNfF(Nonafluorobutanesulfonyl fluoride) is produced on industrial scale by anodic fluorination of sulfolene (1, Scheme 1),3 therefore it is a fairly cheap reagent and commercially available from several suppliers. The compound is bench-stable and storable for years, nontoxic and easy to handle.
synthesis of Nonafluorobutanesulfonyl fluoride
Potassium nonafluoro-1-butanesulfonate Perflurohexane sulphonyl fluoride Sulfosulfuron 1,4-DIFLUOROBUTANE Perfluoro n-butylsulfonic acid N-(n-Butyl)thiophosphoric triamide sodium fluoride 1H,4H-OCTAFLUOROBUTANE Perfluorotriethylamine 1H-NONAFLUOROBUTANE Nonafluorobutane-1-sulfonic acid N-BUTANESULFONYL FLUORIDE 2,2-DIFLUOROPROPYLSULFINYL FLUORIDE DECAFLUOROBUTANE FLUORIDE STANDARD TRIFLUOROMETHANESULFONYL FLUORIDE 1,1,1,2,2,3,3,4-OCTAFLUOROBUTANE Tosyl cyanide

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