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Nonafluorobutanesulfonyl fluoride

CAS No.
375-72-4
Chemical Name:
Nonafluorobutanesulfonyl fluoride
Synonyms
PBSF;1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl fluoride;PERFLUORO-1-BUTANESULFONYL FLUORIDE;FC-4;PERFLUOROBUTANESULFONYL FLUORIDE;Perfluoro n-butylsulfonyl fluoride;Nonafluorobutane-1-sulfonyl fluoride;Nonaflylfluoride;FX-4;50KGS/DRUM
CBNumber:
CB3208090
Molecular Formula:
C4F10O2S
Molecular Weight:
302.09
MDL Number:
MFCD00007422
MOL File:
375-72-4.mol
MSDS File:
SDS
Last updated:2024-10-29 11:48:30

Nonafluorobutanesulfonyl fluoride 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
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)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS05
Signal word  Danger
Hazard statements  H314
Precautionary statements  P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405
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
NFPA 704
1
3 0

Nonafluorobutanesulfonyl fluoride price More Price(41)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 319732 Perfluoro-1-butanesulfonyl fluoride 96% 375-72-4 25g $98.5 2024-03-01 Buy
Sigma-Aldrich 319732 Perfluoro-1-butanesulfonyl fluoride 96% 375-72-4 100g $194 2024-03-01 Buy
TCI Chemical P1098 Perfluoro-1-butanesulfonyl Fluoride >93.0%(GC) 375-72-4 25g $79 2024-03-01 Buy
TCI Chemical P1098 Perfluoro-1-butanesulfonyl Fluoride >93.0%(GC) 375-72-4 250g $460 2024-03-01 Buy
Alfa Aesar B21322 Nonafluorobutanesulfonyl fluoride, 90+% 375-72-4 5g $24.65 2024-03-01 Buy
Product number Packaging Price Buy
319732 25g $98.5 Buy
319732 100g $194 Buy
P1098 25g $79 Buy
P1098 250g $460 Buy
B21322 5g $24.65 Buy

Nonafluorobutanesulfonyl fluoride Chemical Properties,Uses,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.

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.

660-12-8
375-72-4
Synthesis of Nonafluorobutanesulfonyl fluoride from N-BUTANESULFONYL FLUORIDE
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US $50.00 / kg 1kg 99% 1000 hebei hongtan Biotechnology Co., Ltd
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US $2.00 / kg 1kg 99% 500mt Jinan Finer Chemical Co., Ltd
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US $120.00 / kg 1kg 99% 20ton Hebei Zhuanglai Chemical Trading Co.,Ltd
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 Nonafluorobutanesulphonylfluoride95% Nonafluorobutane-1-sulphonyl fluoride, 1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulphonyl fluoride Perfluorobutane-1-sulphonyl fluoride 95% Perfluoro-1-butanesulfonyl fluoride 96% Nofluorobutanesulfonyl fluoride NONAFLUOROBUTANESULFONYL FLUORIDE NONAFLUOROBUTANESULPHONYL FLUORIDE NONAFLUORO-1-BUTANESULFONYL FLUORIDE PERFLUOROBUTANESULPHONYL FLUORIDE 1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonylfluorid 1,1,2,2,3,3,4,4,4-Nonafluoro-1-butanesulfonylfluoride 1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4-nonafluoro- 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulphonyl fluoride Perfluorobutansulfonylfluoride FX-4 Nonafluorobutanesulphonyl fluoride 95% Perfluorobutansulfonylfluoride-RM60 50KGS/DRUM Perfluoro-1-butanesulfonylfluoride[FPBS] uoro-1-butanesuL Perfluoro-1-butanesulfonyl fluoride, 92%, for synthesis Perfluoro-1-butanesulfonylFluoride> Hot sell Nonafluorobutanesulfonyl fluoride 375-72-4 FC-4 1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl fluoride Nonafluorobutane-1-sulfonyl fluoride PERFLUOROBUTANESULFONYL FLUORIDE PERFLUORO-1-BUTANESULFONYL FLUORIDE Nonaflylfluoride Perfluoro n-butylsulfonyl fluoride Sodium lauryl polyoxyethylene ether sulfate 9004-82-4 PBSF Perfluorobutane-1-sulphonyl fluoride Perfluorobutanesulfonyl fluoride 99% cas 375-72-4 99% Nonafluorobutanesulfonyl fluoride 99% cas 375-72-4 PBSF 99% cas 375-72-4 PerfluoroButanesulfonyl Fluoride(PBF) Perfluorobutanesulfonyl Fluoride / Nonafluorobutanesulfonyl Fluoride 1,1,2,2,3,3,4,4,4-Nonafluorobutanesulfonyl fluoride 375-72-4 375-75-4 745-75-2 CF3CF23SO2F nC4F9SO2 C4F10O2S C4F9SO2F Fluorous Chemistry Fluorous Compounds Organic Building Blocks