Sodium thiomethoxide CAS 5188-07-8

What is Sodium thiomethoxide CAS 5188-07-8?

Sodium thiomethoxide CAS 5188-07-8, also known as sodium methanethiolate, is the sodium conjugate base of methanethiol. Commercially available as a white to off-white solid powder (or as a very faint yellowish-red clear liquid when in aqueous solution), it is a powerful nucleophile extensively used in organic synthesis. It is highly valued for the preparation of methyl thioethers, active pharmaceutical ingredients, and agrochemical intermediates. Because it is highly sensitive to air and moisture, it must be handled carefully; exposure to moist air causes hydrolysis, releasing methanethiol, which has a noxious, distinctive odor.

Specifications

Features

• Powerful Nucleophilic Agent: Acts as a strong nucleophile, making it highly efficient for the SN2 dealkylation of esters and aryl ethers, as well as the synthesis of methyl aryl sulfides from halo-arenes.
• High Chemical Reactivity: Rapidly reacts with various compounds (including trifluoroacetic acid and water) to form active complexes. It is highly moisture-sensitive and requires strict storage under inert gas.
• Broad Synthetic Utility: Serves as a versatile building block and reagent for creating complex sulfur-containing organic compounds, thioethers, and active pharmaceutical forms.
• Predictable Hydrolysis: Undergoes rapid hydrolysis upon exposure to moist air to produce methanethiol (methyl mercaptan), a trait requiring specialized handling but useful in specific controlled reactions.

Applications

• Organic Synthesis & Intermediates: Extensively used as a nucleophile to prepare methylthioethers and other organic compounds (such as ethyl bromide), and for the efficient dealkylation of esters and aryl ethers.
• Pharmaceutical Manufacturing: Functions as a critical reagent in the synthesis of thiol-based suberoylanilide hydroxamic acid (SAHA) analogues (potent histone deacetylase inhibitors) and is used to prepare the C-21 thioether of methyl 16-prednisolonecarboxylate via mesylate displacement.
• Agrochemical Production: Serves as a fundamental raw material and intermediate in the manufacturing of various herbicides and insecticides, including Prometryn, Ametryn, Aldicarb, and Simetryne.
• Antibacterial & Biological Research: Used in reactions with trifluoroacetic acid and water to produce the active form of sodium trifluoroacetate, forming bicyclic heterocycles proven effective against various strains of bacteria.

Packaging

Mikem offers flexible packaging options, including 25 kg of fiber drums for liquid products and 15–25 kg PP/PE bags for powder products, all customizable to meet your specific needs.