Basic information Safety Supplier Related
ChemicalBook >  Product Catalog >  Chemical Reagents >  Organic reagents >  Sulfonates / Sulfinates salts >  Methyl trifluoromethanesulfonate

Methyl trifluoromethanesulfonate

Basic information Safety Supplier Related

Methyl trifluoromethanesulfonate Basic information

Product Name:
Methyl trifluoromethanesulfonate
Synonyms:
  • Methanesulfonicacid,trifluoro-,methylester
  • methyltrifluoromethanesulfinate
  • METHYL TRIFLUOROMETHANESULFONATE FOR SYN
  • Methyl trifluoromethanesulfote
  • Methyl trifluoroMethanesulfona
  • Methanesulfonic acid,1,1,1-trifluoro-, Methyl ester
  • Threefluoro Methanesulfonic acidMethyl ester
  • Methyl trifluoromethanesulfate
CAS:
333-27-7
MF:
C2H3F3O3S
MW:
164.1
EINECS:
206-371-7
Mol File:
333-27-7.mol
More
Less

Methyl trifluoromethanesulfonate Chemical Properties

Boiling point:
94-99 °C(lit.)
Density 
1.45 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.326(lit.)
Flash point:
101 °F
storage temp. 
2-8°C
solubility 
Chloroform (Sparingly), Ethyl Acetate (Slightly)
form 
Liquid
Specific Gravity
1.450
color 
Clear colorless to yellow
Sensitive 
Air Sensitive
BRN 
774772
Stability:
Hygroscopic, Moisture Sensitive, Volatile
InChI
InChI=1S/C2H3F3O3S/c1-8-9(6,7)2(3,4)5/h1H3
InChIKey
OIRDBPQYVWXNSJ-UHFFFAOYSA-N
SMILES
C(F)(F)(F)S(OC)(=O)=O
CAS DataBase Reference
333-27-7(CAS DataBase Reference)
EPA Substance Registry System
Methyl trifluoromethanesulfonate (333-27-7)
More
Less

Safety Information

Hazard Codes 
C,T
Risk Statements 
10-34-20/21/22
Safety Statements 
26-36/37/39-45-16
RIDADR 
UN 2920 8/PG 2
WGK Germany 
3
10
Hazard Note 
Highly Toxic/Corrosive
TSCA 
T
HazardClass 
3.2
PackingGroup 
III
HS Code 
29049020

MSDS

More
Less

Methyl trifluoromethanesulfonate Usage And Synthesis

Chemical Properties

clear colourless to yellow liquid

Uses

Methyl trifluoromethanesulfonate is used as a powerful methylating reagent in chemistry. Further, it is used in the conversion of amines to methyl ammonium triflates. In addition, it is also used in Suzuki reaction.

Application

Methyl trifluoromethanesulfonate, a methylating agent, is commonly used for the pre-methylation of polysaccharides under mild basic conditions.
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.
Additionally, methyl trifluoromethanesulfonate has been utilized in the production of 2-Benzyloxy-1-methylpyridinium trifluoromethanesulfonate.

General Description

Methyl trifluoromethane sulfonate is a brown liquid. Insoluble in water. (NTP, 1992) This material is a very reactive methylating agent, also known as methyl triflate.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Methyl trifluoromethanesulfonate is sensitive to heat. . Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Methyl trifluoromethanesulfonate emits toxic fumes.

Fire Hazard

Methyl trifluoromethanesulfonate is combustible.

Toxicology

Methyl trifluoromethanesulfonate is extremely hazardous. All possible precautions should be taken to avoid inhalation or absorption through the skin. This material is extremely destructive to the tissue of the mucous membranes and upper respiratory tract, eyes, and skin. Inhalation may be fatal as a result of spasm, inflammation, and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Use in a fume hood. 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.

Synthesis

Methyl trifluoromethanesulfonate is commercially available, however it may also be prepared in the laboratory by treating dimethyl sulfate with triflic acid.
CF3SO2OH + (CH3O)2SO2  →  CF3SO2OCH3 + CH3OSO2OH

Purification Methods

Methyl trifluoromethanesulfonate (methyl triflate) [333-27-7] M 164.1, b 97 -97.5o/736mm, 9 9o/~760mm, 100-102o/~760mm, d 4 1.496, n D 1.3238. It is a strong methylating agent but is corrosive and POISONOUS. Fractionate it carefully and collecting the middle fraction (use an efficient fume cupboard) and keep away from moisture. It is a POWERFUL ALKYLATING AGENT and a strong IRRITANT. [IR: Gramstad & Haszeldine J Chem Soc 173 1956 , J Chem Soc 4069 1957 .] Trifluoromethanesulfonic acid (triflic acid) [1493-13-6] M 151.1, boils higher (b 162o/atm), has a pKa of 3.10, and is TOXIC and hygroscopic. [Hansen J Org Chem 30 4322 1965, Kurz & El-Nasr J Am Chem Soc 104 5823 1982, Beilstein 3 IV 34.]

Methyl trifluoromethanesulfonate Preparation Products And Raw materials

Raw materials

Methyl trifluoromethanesulfonateSupplier

Wuhan Pengo Technology.,Ltd. Gold
Tel
027-60707801 13628634921
Email
sunny.w@boronicgroup.com
Aikon International Limited Gold
Tel
025-66113011 18112977050
Email
cb6@aikonchem.com
Haimen Ruiyi Medical Tech Co., LTD Gold
Tel
021-54718086
Email
sales5@ruiyitech.com
Wuhan Huahan Dingcheng New Material Technology Co., Ltd Gold
Tel
+86-027-81388558 18963961905
Email
huahandingcheng@sina.com
Shandong Lingqing Pharmaceutical Technology Co., Ltd. Gold
Tel
18600392407 18668996177
Email
linkingpharm@126.com