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Methyl trifluoromethanesulfonate information


Methyl trifluoromethanesulfonate
Structural formula of methyl triflate
Ball-and-stick model of methyl triflate
Names
Preferred IUPAC name
Methyl trifluoromethanesulfonate
Other names
Trifluoromethanesulfonic acid, methyl ester
Triflic acid, methyl ester, methyl triflate
Identifiers
CAS Number
  • 333-27-7 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9153 checkY
ECHA InfoCard 100.005.793 Edit this at Wikidata
EC Number
  • 206-371-7
PubChem CID
  • 9526
UNII
  • 7B25Z22EPV checkY
UN number 2924
CompTox Dashboard (EPA)
  • DTXSID6049272 Edit this at Wikidata
InChI
  • InChI=1S/C2H3F3O3S/c1-8-9(6,7)2(3,4)5/h1H3 checkY
    Key: OIRDBPQYVWXNSJ-UHFFFAOYSA-N checkY
  • InChI=1/C2H3F3O3S/c1-8-9(6,7)2(3,4)5/h1H3
    Key: OIRDBPQYVWXNSJ-UHFFFAOYAL
SMILES
  • COS(=O)(=O)C(F)(F)F
Properties
Chemical formula
C2H3F3O3S
Molar mass 164.10 g·mol−1
Appearance Colourless Liquid
Density 1.496 g/mL
Melting point −64 °C (−83 °F; 209 K)
Boiling point 100 °C (212 °F; 373 K)
Solubility in water
Hydrolyzes
Hazards[1]
Occupational safety and health (OHS/OSH):
Main hazards
Corrosive
GHS labelling:
Signal word
Danger
Hazard statements
H226, H301, H311, H314, H330
Precautionary statements
P210, P233, P303+P361+P353, P304+P340+P310, P305+P351+P338, P380
Flash point 38 °C (100 °F; 311 K)
Related compounds
Related compounds
Methyl fluorosulfonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Methyl trifluoromethanesulfonate, also commonly called methyl triflate and abbreviated MeOTf, is the organic compound with the formula CF3SO2OCH3. It is a colourless liquid which finds use in organic chemistry as a powerful methylating agent.[2] The compound is closely related to methyl fluorosulfonate (FSO2OCH3). Although there has yet to be a reported human fatality, several cases were reported for methyl fluorosulfonate (LC50 (rat, 1 h) = 5 ppm), and methyl triflate is expected to have similar toxicity based on available evidence.[2][better source needed]

  1. ^ "Methyl trifluoromethanesulfonate". Sigma-Aldrich. Retrieved 31 October 2021.
  2. ^ a b Roger W. Alder; Justin G. E. Phillips; Lijun Huang; Xuefei Huang (2005). "Methyltrifluoromethanesulfonate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm266m.pub2. ISBN 0471936235.

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Methyl trifluoromethanesulfonate

Last Update:

Methyl trifluoromethanesulfonate, also commonly called methyl triflate and abbreviated MeOTf, is the organic compound with the formula CF3SO2OCH3. It...

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Methyl fluorosulfonate

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toxicity, it has largely been replaced by the related reagent methyl trifluoromethanesulfonate. It is prepared by distillation of an equimolar mixture of...

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Sulfonate

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the R2 group is a methyl group and the R1 group is a trifluoromethyl group, the resulting compound is methyl trifluoromethanesulfonate. Sulfonic esters...

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Functional group

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Sulfo RSO3R' (-sulfonyl)oxy- or alkoxysulfonyl- R' R-sulfonate Methyl trifluoromethanesulfonate or Methoxysulfonyl trifluoromethane (prefix) Thiocyanate Thiocyanate...

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Sulfonium

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faster with more electrophilic methylating agents, such as methyl trifluoromethanesulfonate. Sulfonium ions with three different substituents are chiral...

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Ester

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the combined use of titanium tetrachloride and trimethylsilyl trifluoromethanesulfonate". Tetrahedron. 57 (25): 5353–5359. doi:10.1016/S0040-4020(01)00420-3...

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Hafnium trifluoromethanesulfonate

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Saito, Yuki; Yamashita, Yasuhiro; Kobayashi, Shū (2015). "Hafnium Trifluoromethanesulfonate [Hf(OTf)4] as a Unique Lewis Acid in Organic Synthesis". European...

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Triflate

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In organic chemistry, triflate (systematic name: trifluoromethanesulfonate), is a functional group with the formula R−OSO2CF3 and structure R−O−S(=O)2−CF3...

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Benzyl chloroformate

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reflux Benzyl chloroformate, DIPEA, acetonitrile and scandium trifluoromethanesulfonate (Sc(OTf)3) Alternatively, the Cbz group can be generated by the...

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Trimethylsilyl chloride

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trimethylsilyl cyanide, trimethylsilyl azide, and trimethylsilyl trifluoromethanesulfonate (TMSOTf). These compounds are produced by a salt metathesis reaction...

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Acyl group

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Hermannsdorfer, André; Driess, Matthias (2021). "Silicon Tetrakis(trifluoromethanesulfonate): A Simple Neutral Silane Acting as a Soft and Hard Lewis Superacid"...

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List of gases

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Tsutomu; Kumadaki, Itsumaro (January 1979). "Trifluoromethyl trifluoromethanesulfonate (CF3SO2OCF3)". Tetrahedron Letters. 20 (40): 3865–3866. doi:10...

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Silylium ion

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which indicates that the cation is quite "naked". Trimethylsilyl trifluoromethanesulfonate (Me3SiOTf), normally considered a source of electrophilic silicon...

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Trimethylsilyl group

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is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom [−Si(CH3)3], which is in turn bonded to...

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Pyrylium

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Balaban, A. T.; Boulton, A. J. (1973). "2,4,6-Trimethyl-Pyrylium Trifluoromethanesulfonate" (PDF). Organic Syntheses; Collected Volumes, vol. 5, pp. 1114–1116...

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Protecting group

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6-Tetra-O-benzyl-D-glucopyranosylidene Acetals Using Trimethylsilyl Trifluoromethanesulfonate Catalyst", in: Chem. Lett., 1981, 10, pp. 375–376; doi:10.1246/cl...

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Bottromycin

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thioamide via mercury-mediated condensation using mercury (II) trifluoromethanesulfonate (Hg(OTf)2) to yield a branched amidine intermediate. To obtain...

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Trifluoromethylation

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the fluorine lone pair with the radical center's SOMO. Compared to the methyl radical the CF3 radical is pyramidal (angle 107.8 °C ) with a large inversion...

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Borinic acid

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→ BuCH2CH=C(CH3)OBBu2 RCOC2H5 + R2BOTf → RC(OBR2)=CHCH3 (Tf = Trifluoromethanesulfonate) (Z)-Enolates give syn aldol product when reacted with an aldehyde...

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Vinyl cation

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lifetimes. These excellent leaving groups, such as triflate (trifluoromethanesulfonate) and nonaflate (nonafluorobutanesulfonate), are highly prone to...

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List of compounds with carbon number 4

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isobutyltrichlorosilane 18169-57-8 C4H9F3O3SSi trimethylsilyl trifluoromethanesulfonate 27607-77-8 C4H9Li butyl lithium 109-72-8 C4H9N cyclobutylamine...

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Ionic liquid

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hexafluorophosphate (PF6), bis-trifluoromethanesulfonimide (NTf2), trifluoromethanesulfonate (OTf), dicyanamide (N(CN)2), hydrogen sulphate (HSO4), and ethyl...

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Sulfone

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Hernandez, P.; Dubac, J.; Desmurs, J. R. (1999). "Bismuth(III) Trifluoromethanesulfonate: An Efficient Catalyst for the Sulfonylation of Arenes". The Journal...

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Trimethylenemethane complexes

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[Fe{η4-C(CH2)3(L)3] (L = PMe or PMe2Ph) (complex 4) reacts with silver trifluoromethanesulfonate to give the 17-electron cation (Figure 7). Trost, Barry M.; Mata...

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