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18503

Supelco

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
Beilstein/REAXYS Number:
774772
EC Number:
206-371-7
MDL number:
MFCD00000409
UNSPSC Code:
41116105
PubChem Substance ID:
329751681
NACRES:
NA.22

grade

derivatization grade (GC derivatization)

Quality Level

100

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

SMILES string

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

InChI

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

InChI key

OIRDBPQYVWXNSJ-UHFFFAOYSA-N

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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.[1]
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.[2]

Legal Information

LiChropur is a trademark of Merck KGaA, Darmstadt, Germany

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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_germany

WGK 3

flash_point_f

100.4 °F - closed cup

flash_point_c

38 °C - closed cup

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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)
Sylwia Ptasińska et al.
The Journal of chemical physics, 135(21), 214309-214309 (2011-12-14)
Gas phase studies of dissociative electron attachment to simple alkyl (CF(3)SO(3)CH(3)) and aryl (C(6)H(5)SO(3)CF(3) and CF(3)SO(3)C(6)H(4)CH(3)) triflates, model molecules of nonionic photoacid generators for modern lithographic applications, were performed. The fragmentation pathways under electron impact below 10 eV were identified
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
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)
K Någren et al.
Nuclear medicine and biology, 22(2), 235-239 (1995-02-01)
[11C]Methyl triflate was compared with [11C]methyl iodide as a labelled precursor in the synthesis of some commonly used PET radioligands, L-[11C]deprenyl, [11C]m-hydroxyephedrine (MHED), [11C] beta-CIT, [11C] beta-CFT and [11C]SCH 39166 which have been prepared previously in comparatively low yields from
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