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375-72-4 - Nonafluorobutanesulfonyl fluoride, 90+% - Nonaflyl fluoride - Perfluorobutanesulfonyl fluoride - B21322 - Alfa Aesar

B21322 Nonafluorobutanesulfonyl fluoride, 90+%

CAS Number
375-72-4
Synonyms
Nonaflyl fluoride
Perfluorobutanesulfonyl fluoride

Size Price ($) Quantity Availability
5g 21.83
25g 61.64
100g 204.97
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Nonafluorobutanesulfonyl fluoride, 90+%

MDL
MFCD00007422
EINECS
206-792-6

Chemical Properties

Formula
CF3(CF2)3SO2F
Formula Weight
302.09
Melting point
-110°
Boiling Point
65-66°
Flash Point
None
Density
1.750
Refractive Index
1.2810
Sensitivity
Moisture Sensitive
Solubility
Hydrolyses in water.

Applications

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.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents, moisture, baese..

Literature References

Takashi Ikawa,; Tsuyoshi Nishiyama,; Toshifumi Nosaki,; Akira Takagi,; Shuji Akai. A Domino Process for Benzyne Preparation: Dual Activation of o-(Trimethylsilyl)phenols by Nonafluorobutanesulfonyl Fluoride. Org. Lett., . 2011, 13 (7), 730-1733.

Jens Högermeier,; Hans-Ulrich Reissig. Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal-Catalyzed Reaction. Advanced Synthesis & Catalysis. 2009, 351 (17), 2747-2763.

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).

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1813589
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2904.90
TSCA
Yes

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