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Merck
CN

18503

Methyl trifluoromethanesulfonate

derivatization grade (GC derivatization), LiChropur™, 98.0%

Synonym(s):

Methyl triflate

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About This Item

Linear Formula:
CF3SO2OCH3
CAS Number:
333-27-7
Molecular Weight:
164.10
UNSPSC Code:
41116105
NACRES:
NA.22
PubChem Substance ID:
329751681
EC Number:
206-371-7
Beilstein/REAXYS Number:
774772
MDL number:
MFCD00000409

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InChI

1S/C2H3F3O3S/c1-8-9(6,7)2(3,4)5/h1H3

InChI key

OIRDBPQYVWXNSJ-UHFFFAOYSA-N

SMILES string

COS(=O)(=O)C(F)(F)F

grade

derivatization grade (GC derivatization)

assay

≥98.0% (GC), 98.0%

form

liquid

quality

LiChropur™

reaction suitability

reagent type: derivatization reagent
reaction type: Acylations

technique(s)

gas chromatography (GC): suitable

refractive index

n20/D 1.326 (lit.), n20/D 1.327

bp

94-99 °C (lit.)

density

1.45 g/mL at 25 °C (lit.)

storage temp.

2-8°C

Quality Level

100

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General description

Methyl trifluoromethanesulfonate (Methyl triflate) is a strong methylating agent. It is also a powerful alkylating agent and a strong irritant.
Shown to be the most effective monomethylating agent in reactions with potassium enolates.
Useful methylation reagent for the conversion of amines to methyl ammonium triflates.

Application

Methyl trifluoromethanesulfonate was used in the synthesis of 2-Benzyloxy-1-methylpyridinium trifluoromethanesulfonate.

Legal Information

LiChropur is a trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

100.4 °F - closed cup

flash_point_c

38 °C - closed cup

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ9445
BCCH1309
BCBZ3188

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W. L. F. Armarego, Christina Li Lin Chai
Purification of Laboratory Chemicals, 189-189 (2013)
Synthesis, structure, and reactivity of a stabilized phosphiranylium salt.
Helen Jansen et al.
Angewandte Chemie (International ed. in English), 49(32), 5485-5488 (2010-07-06)
Liang Liao et al.
The Journal of organic chemistry, 70(16), 6265-6273 (2005-07-30)
Glycosylation of a disaccharide containing N-acetylglucosamine with rhamnosyl and mannosyl trichloracetimidates under triethysilyl triflate catalysis led to the competitive formation of glycosyl imidates. While the rhamnosyl imidate could be rearranged to the thermodynamically favored trisaccharide, the mannosyl analogue was resistant
Jonathan T Reeves et al.
Organic letters, 12(19), 4388-4391 (2010-09-04)
Aryltrimethylammonium triflates and tetrafluoroborates were found to be highly reactive electrophiles in the Pd-catalyzed cross coupling with aryl Grignard reagents. The coupling reactions proceed at ambient temperature with a nearly stoichiometric quantity of Grignard reagent, and diverse functionality is tolerated.
P H Seeberger et al.
Enantiomer, 1(4-6), 311-323 (1996-01-01)
The "core" pentasaccharide region of high mannose asparagine-linked glycoproteins was synthesized using thioethyl donors and methyl triflate to promote coupling. All monosaccharide units were prepared from glycals. The central mannose residue was installed by inversion of the C2 hydroxyl of
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