Cas no 55791-06-5 (benzyl methanesulfonate)

Benzyl methanesulfonate is an organic sulfonate ester commonly utilized as an alkylating agent in synthetic chemistry. Its key advantages include high reactivity in nucleophilic substitution reactions, making it valuable for introducing benzyl groups in fine chemical and pharmaceutical synthesis. The compound exhibits good stability under controlled conditions, ensuring consistent performance in reactions. Its methanesulfonate leaving group facilitates efficient displacement by nucleophiles, enhancing reaction yields. Benzyl methanesulfonate is particularly useful in the preparation of benzyl-protected intermediates, offering selectivity in complex multi-step syntheses. Proper handling is required due to its potential sensitivity to moisture and heat.
benzyl methanesulfonate structure
benzyl methanesulfonate structure
Product Name:benzyl methanesulfonate
CAS No:55791-06-5
MF:C8H10O3S
MW:186.228201389313
CID:1595314
PubChem ID:148757
Update Time:2025-10-28

benzyl methanesulfonate Chemical and Physical Properties

Names and Identifiers

    • benzyl methanesulfonate
    • benzyl mesylate
    • Methanesulfonic acid, phenylmethyl ester
    • Phenylmethyl methanesulfonate
    • 55791-06-5
    • G71480
    • DTXSID80204362
    • MFCD25964568
    • AKOS026732519
    • ZDKRMIJRCHPKLW-UHFFFAOYSA-N
    • SCHEMBL249386
    • methanesulfonic acid benzyl ester
    • Inchi: 1S/C8H10O3S/c1-12(9,10)11-7-8-5-3-2-4-6-8/h2-6H,7H2,1H3
    • InChI Key: ZDKRMIJRCHPKLW-UHFFFAOYSA-N
    • SMILES: S(C)(=O)(=O)OCC1C=CC=CC=1

Computed Properties

  • Exact Mass: 186.0351
  • Monoisotopic Mass: 186.035
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 3
  • Complexity: 209
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 51.8A^2
  • XLogP3: 1.1

Experimental Properties

  • Density: 1.244
  • Boiling Point: 341.8°C at 760 mmHg
  • Flash Point: 160.5°C
  • Refractive Index: 1.534
  • PSA: 43.37

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Additional information on benzyl methanesulfonate

Benzyl Methanesulfonate (CAS No. 55791-06-5): Properties, Applications, and Market Insights

Benzyl methanesulfonate (CAS No. 55791-06-5) is an organic sulfonate ester widely used in pharmaceutical synthesis, organic chemistry research, and specialty chemical applications. This compound, also known as benzyl mesylate, serves as a versatile alkylating agent and intermediate in the production of various bioactive molecules. With the increasing demand for fine chemicals in the pharmaceutical industry, benzyl methanesulfonate derivatives have gained significant attention from researchers and manufacturers alike.

The molecular structure of benzyl methanesulfonate consists of a benzyl group (C6H5CH2) attached to a methanesulfonate (mesylate) functional group (CH3SO3). This configuration gives the compound its characteristic reactivity as an electrophile in substitution reactions. Recent studies highlight its importance in API synthesis (Active Pharmaceutical Ingredients), particularly in the development of novel drug candidates targeting neurological disorders and anti-inflammatory applications.

In pharmaceutical applications, benzyl methanesulfonate 55791-06-5 demonstrates excellent stability under various reaction conditions, making it preferable to other benzylating agents. Its use in peptide modification and prodrug synthesis has been extensively documented in recent chemical literature. The compound's ability to introduce benzyl groups selectively has made it valuable in creating protected intermediates for complex molecular architectures.

The global market for benzyl mesylate applications shows steady growth, driven by increasing R&D investments in pharmaceutical chemistry. Analytical reports indicate particular demand from contract research organizations (CROs) and academic laboratories focusing on medicinal chemistry innovations. Current manufacturing processes emphasize high-purity production to meet the stringent requirements of pharmaceutical grade materials.

From a safety perspective, proper handling procedures for benzyl methanesulfonate CAS 55791-06-5 follow standard laboratory protocols for organic reagents. While not classified as highly hazardous, appropriate personal protective equipment (PPE) including gloves and eye protection is recommended during handling. The compound's stability profile allows for standard storage conditions, typically at room temperature in airtight containers protected from moisture.

Recent technological advancements have improved the synthesis routes for high purity benzyl methanesulfonate, with many manufacturers now offering customized solutions for specific research needs. These developments align with the growing trend toward green chemistry principles, where efficient synthesis methods minimize waste generation. The compound's role in bioconjugation chemistry has also expanded, particularly in the development of antibody-drug conjugates (ADCs) for targeted cancer therapies.

Quality control standards for benzyl methanesulfonate suppliers typically include rigorous testing for purity (often ≥98% by HPLC), residual solvents, and heavy metal content. Analytical techniques such as NMR spectroscopy, mass spectrometry, and chromatographic methods ensure batch-to-batch consistency. These quality parameters are particularly important for pharmaceutical applications where reagent purity directly impacts reaction outcomes.

The scientific literature contains numerous references to benzyl methanesulfonate uses in asymmetric synthesis and chiral auxiliary chemistry. Its application in constructing complex natural product scaffolds has been demonstrated in several total synthesis projects. Researchers value its predictable reactivity pattern and compatibility with various protecting group strategies in multi-step synthetic sequences.

Looking toward future applications, benzyl methanesulfonate research is exploring its potential in materials science, particularly in polymer modification and surface functionalization. Early studies suggest possible utility in creating specialized coatings and functional materials with tailored properties. These emerging applications could further diversify the market for this versatile chemical intermediate.

For researchers sourcing benzyl methanesulfonate CAS No. 55791-06-5, considerations include supplier reliability, technical support availability, and documentation quality. Many leading chemical providers now offer comprehensive technical data sheets, safety information, and application notes to support experimental work. The compound's commercial availability in various packaging sizes facilitates both small-scale research and larger process development needs.

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