Trifluoromethanesulfonic anhydride: Difference between revisions

Trifluoromethanesulfonic anhydride
Identifiers
CAS Number	358-23-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	61068;
ECHA InfoCard	100.006.016
PubChem CID	67749;
UNII	8W034LHG1U ;
CompTox Dashboard (EPA)	DTXSID501014629 ;
	InChI InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8 Key: WJKHJLXJJJATHN-UHFFFAOYSA-N;
	SMILES C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F;
Properties
Chemical formula	C2F6O5S2
Molar mass	282.13 g·mol−1
Appearance	colourless liquid
Density	1.6770 g/mL
Boiling point	82 °C (180 °F; 355 K)
Hazards
Safety data sheet (SDS)	Fisher MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 03:32, 9 August 2020

Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is the chemical compound with the formula (CF₃SO₂)₂O. It is the acid anhydride derived from triflic acid. This compound is a strong electrophile, useful for introducing the triflyl group, CF₃SO₂. Abbreviated Tf₂O, triflic anhydride is the acid anhydride of the strong acid triflic acid, CF₃SO₂OH.^[2]^[3]

Preparation and uses

Triflic anhydride is prepared by dehydration of triflic acid using P₄O₁₀.^[2]

Triflic anhydride is useful for converting ketones into enol triflates.^[4]

In a representative application, is used to convert an imine into a NTf group.^[5] It will convert phenols into a triflic ester, which enables cleavage of the C-O bond.^[6]^[7]

Assay

The typical impurity in triflic anhydride is triflic acid, which is also a colorless liquid. Samples of triflic anhydride can be assayed by ¹⁹F NMR spectroscopy: −72.6 ppm^[8] vs. −77.3 for TfOH (std CFCl₃).

Safety

It is an aggressive electrophile and readily hydrolyzes to the strong acid triflic acid. It is very harmful to skin and eyes.^[9]

References

^ Bloodworth, A.J.; Curtis, Richard J.; Spencer, Michael D.; Tallant, Neil A. (March 1993). "Oxymetallation. Part 24. Preparation of cyclic peroxides by cycloperoxymercuriation of unsaturated hydroperoxides". Tetrahedron. 49 (13): 2729–2750. doi:10.1016/S0040-4020(01)86350-X.
^ ^a ^b Martínez, A. G.; Subramanian, L. R.; Hanack, M. (2016). "Trifluoromethanesulfonic Anhydride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt247.pub3.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Baraznenok, Ivan L.; Nenajdenko, Valentine G.; Balenkova, Elizabeth S. (May 2000). "Chemical Transformations Induced by Triflic Anhydride". Tetrahedron. 56 (20): 3077–3119. doi:10.1016/S0040-4020(00)00093-4.
^ Cacchi, Sandro; Morera, Enrico; Ortar, Giorgio (2011). "Discussion Addendum for: Palladium-Catalyzed Reduction of Vinyl Trifluoromethanesulfonates to Alkenes: Cholesta-3,5-diene". Organic Syntheses. 88: 260. doi:10.15227/orgsyn.088.0260.
^ Baker, T. J.; Tomioka, M.; Goodman, M. (2002). "Preparation and Use of N,N'-Di-BOC-N''-Triflylguanidine". Organic Syntheses. 78: 91. doi:10.15227/orgsyn.078.0091.
^ McWilliams, J. C.; Fleitz, F. J.; Zheng, N.; Armstrong, III, J. D. "Preparation of n-Butyl 4-Chlorophenyl Sulfide". Organic Syntheses. 79: 43. doi:10.15227/orgsyn.079.0043{{cite journal}}: CS1 maint: multiple names: authors list (link).
^ Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. (1999). "(R)-(+)- and (S)-(−)-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl (BINAP)". Organic Syntheses. 76: 6. doi:10.15227/orgsyn.076.0006.
^ Dell'Amico, Daniela Belli; Boschi, Daniele; Calderazzo, Fausto; Labella, Luca; Marchetti, Fabio (28 February 2002). "Synthesis, and crystal and molecular structures of the triflato and trifluoroacetato complexes of zinc, Zn(O3SCF3)2(DME)2 and [Zn(O2CCF3)2(DME)]n" (PDF). Inorganica Chimica Acta. 330 (1): 149–154. doi:10.1016/S0020-1693(01)00739-3.
^ "MSDS - 176176". www.sigmaaldrich.com. Retrieved 2020-08-09.

[1] Bloodworth, A.J.; Curtis, Richard J.; Spencer, Michael D.; Tallant, Neil A. (March 1993). "Oxymetallation. Part 24. Preparation of cyclic peroxides by cycloperoxymercuriation of unsaturated hydroperoxides". Tetrahedron. 49 (13): 2729–2750. doi:10.1016/S0040-4020(01)86350-X.

[eros-2] Martínez, A. G.; Subramanian, L. R.; Hanack, M. (2016). "Trifluoromethanesulfonic Anhydride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt247.pub3.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[3] Baraznenok, Ivan L.; Nenajdenko, Valentine G.; Balenkova, Elizabeth S. (May 2000). "Chemical Transformations Induced by Triflic Anhydride". Tetrahedron. 56 (20): 3077–3119. doi:10.1016/S0040-4020(00)00093-4.

[4] Cacchi, Sandro; Morera, Enrico; Ortar, Giorgio (2011). "Discussion Addendum for: Palladium-Catalyzed Reduction of Vinyl Trifluoromethanesulfonates to Alkenes: Cholesta-3,5-diene". Organic Syntheses. 88: 260. doi:10.15227/orgsyn.088.0260.

[5] Baker, T. J.; Tomioka, M.; Goodman, M. (2002). "Preparation and Use of N,N'-Di-BOC-N''-Triflylguanidine". Organic Syntheses. 78: 91. doi:10.15227/orgsyn.078.0091.

[6] McWilliams, J. C.; Fleitz, F. J.; Zheng, N.; Armstrong, III, J. D. "Preparation of n-Butyl 4-Chlorophenyl Sulfide". Organic Syntheses. 79: 43. doi:10.15227/orgsyn.079.0043{{cite journal}}: CS1 maint: multiple names: authors list (link).

[7] Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. (1999). "(R)-(+)- and (S)-(−)-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl (BINAP)". Organic Syntheses. 76: 6. doi:10.15227/orgsyn.076.0006.

[Amico2002-8] Dell'Amico, Daniela Belli; Boschi, Daniele; Calderazzo, Fausto; Labella, Luca; Marchetti, Fabio (28 February 2002). "Synthesis, and crystal and molecular structures of the triflato and trifluoroacetato complexes of zinc, Zn(O3SCF3)2(DME)2 and [Zn(O2CCF3)2(DME)]n" (PDF). Inorganica Chimica Acta. 330 (1): 149–154. doi:10.1016/S0020-1693(01)00739-3.

[9] "MSDS - 176176". www.sigmaaldrich.com. Retrieved 2020-08-09.

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@@ Line 1: / Line 1: @@
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-| ImageName = Skeletal formula of triflic anhydride
+| ImageName      = Skeletal formula of triflic anhydride
-| ImageFileR1 = Trifluoromethanesulfonic anhydride Space Fill.png
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@@ Line 21: / Line 24: @@
 |  StdInChIKey = WJKHJLXJJJATHN-UHFFFAOYSA-N
 }}
-|Section2={{Chembox Properties
+| Section2       = {{Chembox Properties
 | C=2 | F=6 | O=5 | S=2
+| Appearance = colourless liquid
 | MeltingPt =
 | BoilingPtC = 82 <ref>{{cite journal|last1=Bloodworth|first1=A.J.|last2=Curtis|first2=Richard J.|last3=Spencer|first3=Michael D.|last4=Tallant|first4=Neil A.|title=Oxymetallation. Part 24. Preparation of cyclic peroxides by cycloperoxymercuriation of unsaturated hydroperoxides.|journal=Tetrahedron|date=March 1993|volume=49|issue=13|pages=2729–2750|doi=10.1016/S0040-4020(01)86350-X}}</ref>
 | Density = 1.6770 g/mL
 }}
+| Section3       =
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+| Section5       =
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 | FlashPt =

Revision as of 03:32, 9 August 2020

Preparation and uses

Assay

Safety

See also

References