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.)

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

InChI

1S/C4F10O2S/c5-1(6,3(9,10)11)2(7,8)4(12,13)17(14,15)16

InChIKey

LUYQYZLEHLTPBH-UHFFFAOYSA-N

SMILES

FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O

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

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45-25

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

10-21

Hazard Note 

Corrosive

TSCA 

TSCA listed

HazardClass 

8

PackingGroup 

II

HS Code 

29049090

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Skin Corr. 1B

MSDS

• Language:English Provider:Nonafluorobutanesulfonyl fluoride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Nonafluorobutanesulfonyl fluoride Usage And Synthesis

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.

Uses

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.

Uses

Nonafluorobutanesulfonyl fluoride (NfF, NBSF, PBSF) 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].

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.

reaction suitability

reaction type: click chemistry

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.

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.

Nonafluorobutanesulfonyl fluoride(375-72-4)Related Product Information

• Phenylmethylsulfonyl fluoride
• Dimethyl sulfone
• Sulfosulfuron
• Potassium nonafluoro-1-butanesulfonate
• Perfluorobutyl iodide
• SULFURYL FLUORIDE
• Tosyl cyanide
• Heptafluorobutyric acid
• TRIFLUOROMETHANESULFONYL FLUORIDE
• Perfluorotriethylamine
• FLUORIDE STANDARD
• Perflurohexane sulphonyl fluoride
• Perfluoro-1-iodohexane
• 1H,1H,2H,2H-PERFLUORO-1-OCTANOL
• N-(n-butyl)thiophosphoric triamide
• Heptadecafluorooctanesulfonic acid tetraethylammonium salt
• Perfluorotributylamine
• Perfluoro-1-octanesulfonyl fluoride