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515906

Sigma-Aldrich

Mercury(II) trifluoromethanesulfonate

≥95% trace metals basis

Synonym(s):

Hg(OTf)2

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About This Item

Linear Formula:
(CF3SO3)2Hg
CAS Number:
49540-00-3
Molecular Weight:
498.73
MDL number:
MFCD00144746
UNSPSC Code:
12352300
PubChem Substance ID:
24873853
NACRES:
NA.22

assay

≥95% trace metals basis

reaction suitability

core: mercury
reagent type: catalyst

mp

>350 °C (lit.)

SMILES string

[Hg++].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F

InChI

1S/2CHF3O3S.Hg/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2

InChI key

BPVYMDMPLCOQPJ-UHFFFAOYSA-L

Application

Efficient olefin cyclization agent, effective for the preparation of polycyclic terpenoids.[1]
Polyene cyclization, oxymercuration, catalytic hydration of alkynes, catalytic hydrative enyne cyclization, catalytic arylyne cyclization, catalytic biomimetic tandem cyclization, catalyticketoalkyne cyclization leading to furans, catalytic cyclization of propargyl tert-butyl carbonates leading to cyclic carbonates, catalytic cycloisomerization of alkynyl aniline derivatives leading toindoles, catalytic alkynoic acid cyclization leading to lactones, catalytic glycosylation

Disclaimer

For U.S. Customers: Contains mercury; Do not place in trash - dispose according to local, state, or federal laws.

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Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SLBW7154
SLBQ5912V
SLBR0488V
SLBF4731
SLBC4345

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Mugio Nishizawa et al.
Organic letters, 5(10), 1609-1611 (2003-05-09)
[reaction: see text] Hg(OTf)(2) exhibits remarkable catalytic activity for the hydroxylative cyclization of 1,6-enynes. The present procedure should involve a sequence of mercuration of a terminal alkyne, carbocyclization, hydration, and protodemercuration that regenerates the catalyst.
Nishizawa, M.; Morikuni, E. et al.
Synlett, 169-169 (1995)
Nishizawa, M. et al.
Tetrahedron Letters, 40, 1153-1153 (1999)
Nishizawa, M.; Kashima, T. et al.
Heterocycles, 54, 629-629 (2001)

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