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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.
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.

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBW7154
SLBQ5912V
SLBR0488V
SLBF4731
SLBC4345

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Nishizawa, M.; Kashima, T. et al.
Heterocycles, 54, 629-629 (2001)
Nishizawa, M.; Morikuni, E. et al.
Synlett, 169-169 (1995)
Nishizawa, M. et al.
Tetrahedron Letters, 40, 1153-1153 (1999)
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.

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