Description
Methyl trifluoromethanesulfonate( CAS: 333-27-7, Methanesulfonicacid,trifluoro-,methylester;methyltrifluoromethanesulfinate;METHYLTRIFLUOROMETHANESULFONATEFORSYN;Methyltrifluoromethanesulfote;MetChemicalbookhyltrifluoroMethanesulfona;Methanesulfonicacid,1,1,1-trifluoro-,Methylester;ThreefluoroMethanesulfonicacidMethylester;Methyltrifluoromethanesulfate) is a highly useful class of trifluoromethanesulfonate reagents in organic synthesis, commonly employed as alkylating agents. Due to the strong electron-withdrawing nature of the trifluoromethanesulfonyl group, these compounds exhibit significantly higher reactivity compared to conventional alkylating agents, such as alkyl chlorides or alkyl sulfonates. Among this class, methyl trifluoromethanesulfonate is relatively stable, while other trifluoromethanesulfonate esters are prone to side reactions like elimination or rearrangement. Therefore, their synthesis and workup must be carried out under mild conditions.
◆Chemical Properties
|
Property |
Value |
|---|---|
|
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 Conditions |
2–8 °C |
|
Solubility |
Slightly soluble in chloroform, ethyl acetate |
|
Form |
Liquid |
|
Color |
Transparent colorless to yellow |
|
Specific Gravity |
1.450 |
|
Sensitivity |
Air Sensitive |
|
BRN |
774772 |
|
Stability |
Hygroscopic, Moisture-sensitive, Volatile |
◆Applications
|
Sr. No. |
Description |
Application |
|---|---|---|
|
1 |
Methylating reagent & organic sulfonate intermediate |
Pharmaceutical intermediate synthesis (e.g., for prodrug activation, nucleoside/heterocycle methylation) & chemical derivatization of bioactive molecules |
|
2 |
Activating agent for hydroxyl/amine functional groups |
Facilitates O - methylation / N - methylation in drug candidate synthesis (e.g., for kinase inhibitors, antiviral nucleosides) |
|
3 |
Electrophilic sulfonate ester in organic synthesis |
Enables selective alkylation in multi - step pharmaceutical synthesis (e.g., for peptidomimetics, CNS - active agents) |
|
4 |
Protecting group auxiliary (via methylation) |
Temporarily protects hydroxyl/amine groups during complex molecule assembly (e.g., in peptide - drug conjugate synthesis) |
|
5 |
Catalyst/activator in coupling reactions |
Assists in C - N / C - O bond formation for constructing pharmacologically active scaffolds (e.g., in anti - tumor, anti - viral drug design) |
◆Product Specifications
Methyl trifluoromethanesulfonate (CAS NO.333-27-7) should be handled according to standard chemical industry and pharmaceutical intermediate safety procedures. Appropriate industrial hygiene and protective measures must be followed during handling, storage and operation.
- Use appropriate personal protective equipment (PPE)
- Avoid inhalation of vapor or mist and contact with skin, eyes and clothing
- Handle in controlled, well-ventilated environments
- Keep away from heat, sparks, open flames and hot surfaces
- Protect from moisture and avoid contact with water
- Follow chemical handling, storage and containment protocols
- Refer to Safety Data Sheet (SDS) for detailed safety, handling and storage information
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