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Nonafluorobutanesulfonyl fluoride

CAS No.375-72-4
Chemical Name:Nonafluorobutanesulfonyl fluoride
CBNumber:CB3208090
Molecular Formula:C4F10O2S
Formula Weight:302.09
MOL File:375-72-4.mol

Nonafluorobutanesulfonyl fluoride Property

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
InChIKey LUYQYZLEHLTPBH-UHFFFAOYSA-N
CAS DataBase Reference 375-72-4(CAS DataBase Reference)
FDA UNII WC4FPA9BCM
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)
UNSPSC Code 12352100
NACRES NA.22

Safety

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 :Yes
HazardClass :8
PackingGroup :II
HS Code :29049090

NFPA 704:

	1
3		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H314
Precautionary statements P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405

Nonafluorobutanesulfonyl fluoride Price More Price(6)

Brand: Sigma-Aldrich(India)
Product number: 319732
Product name : Perfluoro-1-butanesulfonyl fluoride
Purity: 96%
Packaging: 25G
Price: ₹5443.8
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 319732
Product name : Perfluoro-1-butanesulfonyl fluoride
Purity: 96%
Packaging: 100G
Price: ₹14738.35
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: P1098
Product name : Perfluoro-1-butanesulfonyl Fluoride
Purity: min. 96.0 %
Packaging: 25G
Price: ₹4800
Updated: 2022/05/26
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Brand: TCI Chemicals (India)
Product number: P1098
Product name : Perfluoro-1-butanesulfonyl Fluoride
Purity: min. 96.0 %
Packaging: 250G
Price: ₹25700
Updated: 2022/05/26
Buy: Buy

Brand: ottokemi
Product number: P 4722
Product name : Perfluoro-1-butanesulfonyl fluoride, 96%
Purity:
Packaging: 25gm
Price: ₹5508
Updated: 2022/05/26
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Nonafluorobutanesulfonyl fluoride Chemical Properties,Usage,Production

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 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].
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.
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.