Ethyl trifluoromethanesulfonate Property

Boiling point:

115 °C (lit.)

Density 

1.374 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.336(lit.)

Flash point:

96 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform, Methanol (Slightly)

form 

Oil

color 

Colourless

Specific Gravity

1.374

Water Solubility 

Hydrolyzes in water.

Sensitive 

Hygroscopic

BRN 

1770746

Stability:

Volatile

InChIKey

UVECLJDRPFNRRQ-UHFFFAOYSA-N

CAS DataBase Reference

425-75-2(CAS DataBase Reference)

EPA Substance Registry System

Methanesulfonic acid, trifluoro-, ethyl ester (425-75-2)

Safety

Hazard Codes 

C,T,F

Risk Statements 

10-34

Safety Statements 

16-26-36/37/39-45

RIDADR 

UN 2920 8/PG 2

WGK Germany 

2

F 

3

Hazard Note 

Highly Toxic

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29049090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Ethyl trifluoromethanesulfonate Chemical Properties,Usage,Production

Description

Ethyl trifluoromethanesulfonate is a cationic polymerization agent used to produce polyurethane, polyacrylate, and other synthetic resins. It is an effective drug for the treatment of HIV infection and chronic bronchitis. Ethyl trifluoromethanesulfonate has been shown to inhibit the replication of HIV-1 virus at concentrations as low as 1 μM when tested in vitro. The mechanism of this drug's anti-HIV activity is unknown and may involve the inhibition of reverse transcriptase or proteases. Ethyl trifluoromethanesulfonate can be detected in vivo up to 4 hours after administration. This drug is metabolized into trifluoroacetic acid by esterases, glycosidases, and/or oxidases.

Chemical Properties

Clear colorless to yellow liquid

Uses

Ethyl trifluoromethanesulfonate is a powerful ethylating agent. due to the strong electron-absorbing ability of trifluoromethanesulfonyl, the reactivity is much higher than that of conventional alkylation reagents such as bichloride or alkyl sulfonate.

Synthesis

Triethyl orthoformate (4.44g,30mmol) was slowly added to trifluoromethanesulfonic anhydride (8.47g,30mmol) under ice bath, transferred to 25°C for reaction, monitored by NMR for 15 min, and the reaction was completed, distilled under reduced pressure to obtain 10.15g of ethyl trifluoromethanesulfonate colorless liquid in 94% yield.

Purification Methods

The ester reacts slowly with H2O and aqueous alkali. If its IR has no OH bands (~3000 cm-1) then purify it by redistillation. If OH bands are present, then dilute with dry Et2O and shake (carefully) with aqueous NaHCO3 until effervescence ceases, then wash with H2O and dry (MgSO4), filter, evaporate and distil the residue under a slight vacuum then at atmospheric pressure in a N2 atmosphere. IT IS A POWERFUL ALKYLATING AGENT, AND THE FUMES ARE VERY TOXIC — PERFORM ALL OPERATIONS IN AN EFFICIENT FUME CUPBOARD. [Gramstad & Haszeldine J Chem Soc 173 1956, Howells & McCown Chem Rev 77 69 1977, Beilstein 3 IV 34.]