Methyl 2-Sulfanylacetate (CAS 2365-48-2) – High-Purity Methyl Thioglycolate for Polymer Chain Transfer and Chemical Synthesis

Methyl 2-Sulfanylacetate, commonly referred to as Methyl Thioglycolate, Mercaptoacetic Acid Methyl Ester, Methyl Mercaptoacetate, or Thioglycolic Acid Methyl Ester, is a clear, colorless to pale yellow liquid organosulfur compound with a characteristic thiol odor. Bearing CAS number 2365-48-2 and molecular formula C₃H₆O₂S (molecular weight 106.14 g/mol), this versatile methyl ester of thioglycolic acid excels as a reactive intermediate and performance additive in polymerization and fine chemical applications.

Key Properties-Methyl 2-Sulfanylacetate(Mercaptoacetic Acid Methyl Ester)

  • Appearance: Colorless to slightly yellow clear liquid
  • Purity: Typically ≥95–98% (GC)
  • Density: ~1.187 g/mL at 25°C
  • Boiling Point: 42–43°C at 10 mmHg; ~148–149°C at atmospheric pressure
  • Flash Point: ~30°C (closed cup, flammable)
  • Melting Point: ~-24°C
  • Refractive Index: ~1.465–1.467
  • Solubility: Soluble in organic solvents (alcohols, ethers, ketones); partially soluble in water
  • Characteristic Feature: Highly reactive -SH (thiol) group enabling radical chain transfer, nucleophilic addition, and metal coordination

Primary Applications-Methyl 2-Sulfanylacetate(Mercaptoacetic Acid Methyl Ester)

Methyl Thioglycolate is prized for its efficiency in controlling polymer molecular weight and structure:

  • Chain Transfer Agent (CTA) in Polymerization — Widely used in free-radical polymerization (e.g., acrylics, methacrylates, vinyl acetate, styrene-based polymers) to regulate chain length, reduce molecular weight, narrow polydispersity, and improve processability. Essential for producing low-viscosity resins, adhesives, coatings, and specialty polymers with consistent performance.
  • PVC and Polymer Stabilizers — Serves as an intermediate or co-stabilizer in the synthesis of organotin mercaptide heat stabilizers; enhances thermal stability in PVC processing by mitigating degradation.
  • Organic Synthesis Intermediate — Key building block for synthesizing heterocyclic compounds (e.g., tetrahydrothiopyran and thiophene derivatives), thiol-functionalized materials, and pharmaceutical/fine chemical intermediates.
  • Other Uses — Employed in photoinitiated polymerization, cross-linking agents, pigment dispersion aids, thiol-ene click chemistry, and as a precursor in organocatalysis or gold nanorod functionalization.

Its methyl ester structure offers lower volatility and better handling compared to free thioglycolic acid, while maintaining high thiol reactivity.

Advantages

  • Highly effective chain transfer constant for precise molecular weight control in radical systems
  • Improves polymer properties such as viscosity, solubility, and film formation
  • Versatile in both aqueous and solvent-based polymerization recipes
  • High reactivity for thiol-based reactions with minimal side products
  • Reliable purity and consistency for industrial-scale applications

Frequently Asked Questions (FAQs)

What is the primary function of Methyl Thioglycolate in polymerization?

It acts as a chain transfer agent (CTA) that transfers growing radical chains to the thiol group, terminating one chain and initiating a new one. This controls average molecular weight, reduces gel formation, and tailors polymer rheology without significantly affecting conversion rates.

How does Methyl Thioglycolate compare to other chain transfer agents like thioglycolic acid or dodecanethiol?

Methyl Thioglycolate offers a balanced chain transfer constant suitable for many acrylate/vinyl systems, with the advantage of lower odor intensity and better compatibility than free thioglycolic acid. It is often preferred over longer-chain thiols for applications requiring minimal impact on final properties.

Is Methyl Thioglycolate used in cosmetic or hair care products?

While related thioglycolates (e.g., ammonium or monoethanolamine salts) are common in perms and straighteners, the methyl ester form is primarily industrial/polymer-grade due to its ester nature and higher volatility. It is not typically used in direct cosmetic formulations.

What safety considerations apply to Methyl Thioglycolate?

It is flammable (flash point ~30°C), has a strong thiol odor, and can cause skin/eye irritation or sensitization. Handle with appropriate PPE (gloves, goggles, ventilation), avoid ignition sources, and store under inert atmosphere if needed to prevent oxidation.

How should Methyl Thioglycolate be stored?

Store in tightly sealed containers in a cool, dry, well-ventilated area away from heat, sparks, strong oxidizers, and bases. Protect from light and air to maintain thiol integrity; shelf life is typically 12–24 months under recommended conditions.

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