1,1,2,2,3,3,4,4,4-Nonafluorbutan-1-sulfonylfluorid

Bezeichnung:1,1,2,2,3,3,4,4,4-Nonafluorbutan-1-sulfonylfluorid

CAS-Nr375-72-4

Englisch Name:Nonafluorobutanesulfonyl fluoride

CBNumberCB3208090

SummenformelC4F10O2S

Molgewicht302.09

MOL-Datei375-72-4.mol

Synonyma

1,1,2,2,3,3,4,4,4-Nonafluorbutan-1-sulfonylfluorid

1,1,2,2,3,3,4,4,4-Nonafluorbutan-1-sulfonylfluorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	-110°C
Siedepunkt	64 °C (lit.)
Dichte	1.682 g/mL at 25 °C (lit.)
Dampfdruck	16.665kPa at 20℃
Brechungsindex	n20/D 1.3(lit.)
Flammpunkt	65-66°C
storage temp.	Keep in dark place,Sealed in dry,Store in freezer, under -20°C
Löslichkeit	Chloroform (Sparingly), Methanol (Sparingly)
Aggregatzustand	Liquid
Farbe	Colorless to yellow
Wichte	1.682
Wasserlöslichkeit	Hydrolyses in water.
Sensitive	Moisture Sensitive
BRN	1813589
Stabilität	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 Datenbank	375-72-4(CAS DataBase Reference)
NIST chemische Informationen	Nonafluorobutanesulfonyl fluoride(375-72-4)
EPA chemische Informationen	1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4-nonafluoro- (375-72-4)

Sicherheit

Kennzeichnung gefährlicher	C
R-Sätze:	34
S-Sätze:	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
Speicherklasse	8A - Combustible corrosive hazardous materials
Hazard Classifications	Skin Corr. 1B

Gefahreninformationscode (GHS)

Nonafluorobutanesulfonyl fluoride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R34:Verursacht Verätzungen.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S25:Berührung mit den Augen vermeiden.
Beschreibung
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.
Chemische Eigenschaften
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.
Verwenden
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].
Verwenden
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
Synthese
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.
Lager
Store in amber colored bottles protected from light; for prolonged storage, PVC bottles are recommended.
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

1,1,2,2,3,3,4,4,4-Nonafluorbutan-1-sulfonylfluorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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