nonafluorobutane-1-sulfonyl fluoride

• ChemBase ID: 98621
• Molecular Formular: C4F10O2S
• Molecular Mass: 302.090632
• Monoisotopic Mass: 301.94593244
• SMILES: FC(C(F)(C(F)(F)C(F)(F)S(=O)(=O)F)F)(F)F
• Canonical SMILES: FC(C(C(S(=O)(=O)F)(F)F)(F)F)(C(F)(F)F)F
• InChI: InChI=1S/C4F10O2S/c5-1(6,3(9,10)11)2(7,8)4(12,13)17(14,15)16
• InChIKey: LUYQYZLEHLTPBH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: nonafluorobutane-1-sulfonyl fluoride
• IUPAC Traditional name: nonafluorobutane-1-sulfonyl fluoride
• Synonyms: Perfluoro-1-butanesulfonyl fluoride; Perfluoro-1-butanesulfonyl fluoride; Nonafluoro-1-butanesulfonyl fluoride; Nonafluorobutanesulphonyl fluoride; Perfluorobutanesulphonyl fluoride 95%; Nonaflyl fluoride; Perfluorobutanesulfonyl fluoride; Nonafluorobutanesulfonyl fluoride; 全氟丁基磺酰氟; 全氟丁烷磺酰氟; 九氟丁烷磺酰氟

Database IDs

• CAS Number: 375-72-4
• EC Number: 206-792-6
• MDL Number: MFCD00007422
• Beilstein Number: 1813589
• PubChem SID: 162085017; 24859184; 24888919
• PubChem CID: 67814

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.1050642
• LogD (pH = 7.4): 3.1050642
• Log P: 3.1050642
• Molar Refractivity: 31.2436 cm^3
• Polarizability: 12.803546 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -110°C; -110°C
• Boiling Point: 64 °C(lit.); 64-66°C; 65-66°C
• Flash Point: None; none°C
• Density: 1.682; 1.682 g/mL at 25 °C(lit.); 1.716 g/mL at 20 °C(lit.); 1.750
• Refractive Index: 1.2810; n20/D 1.298(lit.); n20/D 1.3(lit.)

Safety Information

• Storage Warning: Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 3265 8/PG 2

Product Information

• Purity: ≥95.0% (GC); 90+%; 96%
• Grade: purum p.a.
• Linear Formula: CF3(CF2)3SO2F

DETAILS

Sigma Aldrich - 319732

Packaging
25, 100 g in poly bottle

Sigma Aldrich - 87583

Application
protecting group for organic synthesis

REFERENCES

• Nonaflates of phenols, which are stable to flash chromatography, are attractive precursors for coupling reactions, with alkyl- and arylzinc halides, arylboronic acids (Suzuki) and arylstannanes (Stille), catalyzed by Pd(0) under mild conditions: J. Org. Chem., 63, 203 (1998). Silyl enol ethers, with catalytic TBAF in the presence of molecular sieves, are converted to enol nonaflates which undergo Heck couplings, e.g with styrenes to give 1,3-dienes: Synlett, 1141 (1997).
• Reagent for formation of nonafluorobutanesulfonates (nonaflates) of OH groups (compare Trifluoromethanesulfonic anhydride, A11767), e.g. with triethylamine in ether: Synthesis, 293 (1973); Liebigs Ann. Chem., 20 (1973).