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Sigma-Aldrich

Methyl trifluoromethanesulfonate

≥98%

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:
12352108
PubChem Substance ID:
24850067
NACRES:
NA.22

Quality Level

200

assay

≥98%

form

liquid

refractive index

n20/D 1.326 (lit.)

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 is a strong methylating reagent, commonly used for the pre-methylation of polysaccharides under mild basic conditions.

Application

Methyl trifluoromethanesulfonate can be used as a methylation reagent:
  • In the determination of polysulfides, zerovalent sulfur in sulfide-rich water wells, and polysulfide species in electrolyte of a lithium–sulfur battery using chromatography-based techniques.
  • In reactions with potassium enolates.
  • For the conversion of amines to methyl ammonium triflates.

accessory

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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

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Ring Expansions of 2-Alkenylazetidinium Salts-a New Route to Pyrrolidines and Azepanes
Couty F, et al.
European Journal of Organic Chemistry, 2006(18), 4214-4223 (2006)
Quantitative and Qualitative Determination of Polysulfide Species in the Electrolyte of a Lithium?Sulfur Battery using HPLC ESI/MS with One?Step Derivatization
Zheng D, et al.
Advanced Energy Materials, 5(16) (2015)
Oliver Schuster et al.
Inorganic chemistry, 45(20), 7997-7999 (2006-09-27)
Two cationic carbene complexes with no heteroatom in the ring containing the carbene carbon, trans-bromo(2-methyl-2,6-dihydroisoquinolin-6-ylidene)bis(triphenylphosphine)palladium(II) triflate (3) and trans-chloro(1,2-dimethyl-1,7-dihydroquinolin-7-ylidene)bis(triphenylphosphine)palladium(II) triflate (4), were synthesized by oxidative substitution of Pd(PPh3)4 with N-methylated 6-bromoisoquinolinium and 7-chloro-2-methylquinolinium cations, respectively. Compound 3 was also prepared
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
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