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18503

Supelco

Methyl trifluoromethanesulfonate

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

grade

for 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.
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

Signal Word

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 Code

3 - Flammable liquids

WGK

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
BCBP5664V
BCBN7765V

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W. L. F. Armarego, Christina Li Lin Chai
Purification of Laboratory Chemicals, 189-189 (2013)
Protection of Alcohols Using 2-Benzyloxy-1-Methylpyridinium Trifluoromethanesulfonate: Methyl (R)-(-)-3-Benzyloxy-2-Methyl Propanote.
Poon, Kevin WC, Philip A. Albiniak, and Gregory B. Dudley.
Organic Syntheses, 295-305 (2007)
Convenient gas phase bromination of [11C]methane and production of [11C]methyl triflate.
B H Mock et al.
Nuclear medicine and biology, 26(4), 467-471 (1999-06-26)
T D Wegman et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 57(4), 505-507 (2002-10-04)
This paper describes an improved preparation of [11C]verapamil by reaction of [11C]methyl triflate with desmethylverapamil. The optimal reaction temperature, amount of precursor and reaction time were assessed. With this method [11C]verapamil can be prepared with a reproducible radiochemical yield of
S E Snyder et al.
Nuclear medicine and biology, 25(8), 751-754 (1998-12-24)
Synthesis of 1-[11C]methylpiperidin-4-yl propionate ([11C]PMP), an in vivo substrate for acetylcholinesterase, is reported. An improved preparation of 4-piperidinyl propionate (PHP), the immediate precursor for radiolabeling, was accomplished in three steps from 4-hydroxypiperidine by (a) protection of the amine as the
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