Cas no 67226-78-2 (Ethyl (tert-Butyldimethylsilyl)oxyacetate)

Ethyl (tert-Butyldimethylsilyl)oxyacetate is a protected form of glycolic acid, featuring a tert-butyldimethylsilyl (TBS) group that enhances stability and selectivity in synthetic applications. The TBS protection prevents unwanted side reactions, making it particularly useful in multi-step organic synthesis, including peptide and carbohydrate chemistry. Its ethyl ester moiety offers improved solubility in organic solvents, facilitating handling and reactivity. This compound is commonly employed as a versatile intermediate in the preparation of complex molecules, where controlled deprotection under mild conditions is required. Its robustness under various reaction conditions makes it a valuable reagent for researchers in medicinal and materials chemistry.
Ethyl (tert-Butyldimethylsilyl)oxyacetate structure
67226-78-2 structure
Product Name:Ethyl (tert-Butyldimethylsilyl)oxyacetate
CAS No:67226-78-2
MF:C10H22O3Si
MW:218.365384578705
MDL:MFCD09835572
CID:395154
PubChem ID:11183578
Update Time:2025-05-25

Ethyl (tert-Butyldimethylsilyl)oxyacetate Chemical and Physical Properties

Names and Identifiers

    • Acetic acid, [[(1,1-dimethylethyl)dimethylsilyl]oxy]-, ethyl ester
    • 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]Acetic acid ethyl ester
    • Ethyl 2-(tert-butyldimethylsilyloxy)acetate
    • ethyl 2-[tert-butyl(dimethyl)silyl]oxyacetate
    • Ethyl [(tert-Butyldimethylsilyl)oxy]acetate
    • (tert-butyl-dimethyl-silanyloxy)-acetic acid ethyl ester
    • (tert-butyldimethylsilyloxy)-acetic acid ethyl ester
    • ethyl 2-((tert-butyldimethylsilyl)oxy)acetate
    • ethyl t-butyldimethylsiloxyacetate
    • ethyl tert-butyldimethylsiloxyacetate
    • tert-butyldimethylsilyloxyacetate
    • MFCD09835572
    • Ethyl 2-(t-butyldimethylsilyloxy)acetate
    • Ethyl glycolate, TBDMS derivative
    • AKOS028112102
    • EN300-8660142
    • Ethyl {[tert-butyl(dimethyl)silyl]oxy}acetate
    • FT-0668183
    • 67226-78-2
    • SCHEMBL6220404
    • SY344975
    • AB10111
    • DTXSID20457971
    • ethyl t-butyldimethylsilyloxyacetate
    • Ethyl[(tert-butyldimethylsilyl)oxy]acetate
    • CS-0119884
    • ETHYL 2-[(TERT-BUTYLDIMETHYLSILYL)OXY]ACETATE
    • DB-313285
    • Ethyl (tert-Butyldimethylsilyl)oxyacetate
    • MDL: MFCD09835572
    • Inchi: 1S/C10H22O3Si/c1-7-12-9(11)8-13-14(5,6)10(2,3)4/h7-8H2,1-6H3
    • InChI Key: VMYQJDCENDEETH-UHFFFAOYSA-N
    • SMILES: [Si](C)(C)(C(C)(C)C)OCC(=O)OCC

Computed Properties

  • Exact Mass: 218.13400
  • Monoisotopic Mass: 218.13382109g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 6
  • Complexity: 194
  • 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: 35.5?2

Experimental Properties

  • Density: 0.912
  • Boiling Point: 40-420C
  • Flash Point: 70.2°C
  • Refractive Index: 1.42
  • Solubility: Acetone, Chloroform, Dichloromethane, Ethyl Acetate, Methanol
  • PSA: 35.53000
  • LogP: 2.57130
  • Vapor Pressure: 0.1±0.4 mmHg at 25°C

Ethyl (tert-Butyldimethylsilyl)oxyacetate Security Information

Ethyl (tert-Butyldimethylsilyl)oxyacetate Pricemore >>

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Additional information on Ethyl (tert-Butyldimethylsilyl)oxyacetate

Comprehensive Guide to Ethyl (tert-Butyldimethylsilyl)oxyacetate (CAS No. 67226-78-2): Properties, Applications, and Industry Insights

Ethyl (tert-Butyldimethylsilyl)oxyacetate (CAS No. 67226-78-2) is a specialized silyl-protected ester widely utilized in organic synthesis and pharmaceutical research. This compound, often abbreviated as TBSO-EtOAc, features a tert-butyldimethylsilyl (TBS) protecting group, which enhances its stability and reactivity in complex chemical transformations. Researchers and manufacturers value this reagent for its role in peptide synthesis, carbohydrate chemistry, and as a building block for advanced intermediates.

In recent years, the demand for Ethyl (tert-Butyldimethylsilyl)oxyacetate has surged due to its applications in green chemistry and sustainable synthesis. With growing interest in eco-friendly reagents, this compound’s ability to minimize side reactions and improve yield efficiency aligns with industry trends. Analytical techniques like NMR spectroscopy and HPLC confirm its high purity (>98%), making it a reliable choice for high-throughput screening and drug discovery projects.

The TBS-protected moiety in 67226-78-2 offers selective deprotection advantages, a feature frequently explored in asymmetric synthesis. This property is critical for developing chiral molecules used in biocatalysis and material science. Users often search for "TBSOEtOAc solubility" or "Ethyl (tert-Butyldimethylsilyl)oxyacetate storage conditions," highlighting practical concerns. The compound is typically stored under inert conditions (argon/nitrogen) at 2–8°C to prevent hydrolysis.

From a commercial perspective, CAS 67226-78-2 is supplied by leading fine chemical vendors with certifications like ISO 9001 and REACH compliance. Its pricing reflects the technical grade (e.g., research-grade vs. GMP-grade), with bulk quantities available for industrial-scale applications. Recent patents involving this compound focus on prodrug design and bioconjugation, further driving its relevance in biopharmaceuticals.

For laboratories optimizing cross-coupling reactions, Ethyl (tert-Butyldimethylsilyl)oxyacetate serves as a versatile electrophile. Its compatibility with palladium catalysts and organometallic reagents is well-documented, addressing common queries like "TBSOEtOAc reaction with Grignard." Additionally, its low toxicity profile (non-hazardous per SDS data) makes it preferable over traditional acylating agents.

Emerging studies explore its utility in nanotechnology, particularly for surface functionalization of nanoparticles. As the chemical industry shifts toward precision synthesis, 67226-78-2 exemplifies how tailored reagents can streamline workflows. Future research may expand its role in click chemistry or photoredox catalysis, areas gaining traction in academic and industrial circles.

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