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HomeProduct name listNonafluorobutanesulfonyl fluoride

Nonafluorobutanesulfonyl fluoride

Synonym(s):NfF;Nonafluorobutanesulfonyl fluoride

  • CAS NO.:375-72-4
  • Empirical Formula: C4F10O2S
  • Molecular Weight: 302.09
  • MDL number: MFCD00007422
  • EINECS: 206-792-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-29 11:48:30
Nonafluorobutanesulfonyl fluoride Structural

What is Nonafluorobutanesulfonyl fluoride?

Description

1,1,2,2,3,3,4,4,4-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 properties

Nonafluorobutanesulfonyl 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.

The Uses of Nonafluorobutanesulfonyl fluoride

Benzynes 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.

The Uses of Nonafluorobutanesulfonyl fluoride

Nonafluorobutanesulfonyl fluoride can be used as a general-purpose diazotransfer reagent with high efficiency, wide substrate range, good shelf stability, relatively low cost, and easy purification. It is a favourable alternative to other commonly used diazotransfer reagents[1]. In addition, Nonafluorobutanesulfonyl fluoride was used in the formation of a new dehydrated glycosylation scheme. In contrast to the main classical glycosylation reactions, this scheme glycosylation reaction is carried out under mildly alkaline conditions. In the absence of an external acceptor, the glycosyl hemiacetal undergoes self-condensation, providing the corresponding symmetric 1,1'- disaccharide in high yield[2].

What are the applications of Application

Perfluoro-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.

Synthesis

NfF(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

storage

Store in amber colored bottles protected from light; for prolonged storage, PVC bottles are recommended.

References

[1] JOSE LUIS CHIARA; José R S. Synthesis of α-Diazo Carbonyl Compounds with the Shelf-Stable Diazo Transfer Reagent Nonafluorobutanesulfonyl Azide[J]. Advanced Synthesis & Catalysis, 2011. DOI:10.1002/adsc.201000846.
[2] YU TANG; Biao Y; D Prabhakar Reddy. A dehydrative glycosylation protocol mediated by nonafluorobutanesulfonyl fluoride (NfF)[J]. Tetrahedron, 2021. DOI:10.1016/j.tet.2020.131800.

Properties of Nonafluorobutanesulfonyl fluoride

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.)
Flash point: 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 Gravity 1.682
Water Solubility  Hydrolyses in water.
Sensitive  Moisture Sensitive
BRN  1813589
Stability: Hygroscopic
CAS DataBase Reference 375-72-4(CAS DataBase Reference)
NIST Chemistry Reference Nonafluorobutanesulfonyl fluoride(375-72-4)
EPA Substance Registry System 1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4-nonafluoro- (375-72-4)

Safety information for Nonafluorobutanesulfonyl fluoride

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H314:Skin corrosion/irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P363:Wash contaminated clothing before reuse.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Nonafluorobutanesulfonyl fluoride

InChIKey LUYQYZLEHLTPBH-UHFFFAOYSA-N

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