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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:
774772
EC Number:
206-371-7
MDL number:
MFCD00000409
UNSPSC Code:
12352108
PubChem Substance ID:
24850067
NACRES:
NA.22
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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.)

functional group

fluoro
triflate

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,[1] commonly used for the pre-methylation of polysaccharides under mild basic conditions.[2]

Application

Methyl trifluoromethanesulfonate can be used as a methylation reagent:
  • In the determination of polysulfides, zerovalent sulfur in sulfide-rich water wells,[3] and polysulfide species in electrolyte of a lithium–sulfur battery[4] using chromatography-based techniques.
  • In reactions with potassium enolates.[5]
  • For the conversion of amines to methyl ammonium triflates.[6][7]

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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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

100.4 °F - closed cup

Flash Point(C)

38 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV3673
MKCV6217
MKCW5741
MKCV2467
MKCV2837

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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
Speciation of polysulfides and zerovalent sulfur in sulfide-rich water wells in southern and central Israel
Kamyshny A, et al.
Aquatic Geochemistry, 14(2), 171-192 (2008)
Purification of Laboratory Chemicals, 6 (2009)
Analytical Methods in Wood Chemistry, Pulping, and Papermaking (1998)
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)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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