1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonyl fluoride

Synonym
Product Category
Product Code
CAS Number
MDL Number
Pubchem CID
Reaxys RN
5-hydro-3-oxaoctafluoropentanesulfonyl fluoride,RfSO2F
Perfluoroalkane Sulfonyl Fluorides
KUMIPF06
104729-49-9
MFCD07778617
10881108
5853831
image-155171-Trimethyl(trifluoromethyl)silane_reagent.png
Chemical Name
Molecular Formula
Molecular Weight
Assay(Analysis Method)
Appearance
Boiling Point
Packaging
Storage
1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonyl fluoride
C4HF9O3S
300.10
≥96.0%(GC)
Liquid
70°C/400mmHg
5g,10g,50g,100g,500g,1kg and 25kg
Store at room temperature
Perfluoroalkanosulfonyl fluorides (RfSO2F) are stable,non-toxic,moisture-tolerant and cost effective reagents. In industry, they have been widely empolyed as precursors for the synthesis of highly valued surfactants,pefluoroalkanesulfonic acid salt RfSO3M. Due to the excellent leaving ability of perfluorosulfonate anion(RfSO3-), RfSO2F has been explored and used as an excellent hydroxyl group-activating reagent for fluorination of alcohols to synthesize fluorides, for cyclodehydration of chiral vicinal diols, N-acylamino alcohols, ß-hydroxy sulfonamides and ß-hydroxy thioamides for the synthesis of epoxides and other heterocyclic compounds, for the preparation of acid-sensitive from the substrate of a,ß-unstaturated ketoximes, for dehydration of aldoximes to nitriles, and for the synthesis of diphenylphosphinate esters via the reaction of diphenylphosphine oxide with alcohols.
Some new reactions of poly(per)fluoroalkanesulfonyl fluorides with steroidal molecules. [1]
Bi-functional fluoroalkylation reagents: an introduction to halo-substituted 3-oxa-perfluoroalkanesulfonyl fluorides. [2]
Fluoroalkanosulfonyl fluorides-mediated cyclodehydration of β-hydroxy sulfonamides and β-hydroxy thioamides to the corresponding aziridines and thiazolines. [3]
A new and concise way to enamides by fluoroalkanosulfonyl fluoride mediated Beckmann rearrangement of α,β-unsaturated ketoximes. [4]
Perfluoroalkanosulfonyl fluoride: A useful reagent for dehydration of aldoximes to nitriles. [5]
Perfluoroalkanosulfonyl fluoride-assisted Atherton–Todd-like reaction of diphenylphosphine oxide with alcohols under air generating diphenylphosphinate esters. [6]
References:
[1] W. Tian, Z. Lei, L. Chen, Y. Huang, J. F. Chem., 2000, 101(2), pp 305-308.
[2] C. Zhang, Q. Chen, Y. Guo, J. Xiao, Tetrahedron, 2013, 69, pp 10955-10989.
[3] Z. Yan, C. Guan, Z. Yu, W. Tian, Tetrahedron Lett., 2013, 54, pp 5788-5790.
[4] Z. Yan, Y. Xu, W. Tian, Tetrahedron Lett., 2014, 55, pp 7186-7189.
[5] Z. Yan, H. Tian, D. Zhao, H. Jin, W. Tian, Chinese Chem. Lett., 2016, 27, pp 96-98.
[6] W. Wang, H. Jin, Z. Yan, M. He, S. Lin, W. Tian, Tetrahedron Lett., 2017, 58, pp 3489-3492.
Signal Word
Hazard Statements
Precautionary Statements
HS Code
RIDADR
Legal Information
Danger
H226,H302+H312+H332,H314
P210,P260,P280,P310
2909.19.9090
UN 2920 8(3)/PG II

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