Cas no 39061-59-1 (tert-Butyl 2-Chloro-2-oxoacetate)

Tert-Butyl 2-Chloro-2-oxoacetate is a versatile organic compound primarily used as a reagent in synthetic chemistry. Its key advantages include its role as an effective acylating agent, enabling the introduction of the 2-chloro-2-oxoacetyl group into target molecules. The tert-butyl ester moiety enhances stability, facilitating handling and storage compared to more labile derivatives. This compound is particularly valuable in peptide synthesis and the preparation of heterocyclic compounds, where its reactivity allows for selective transformations under mild conditions. Its well-defined chemical properties make it a reliable choice for applications requiring precise control over reaction pathways.
tert-Butyl 2-Chloro-2-oxoacetate structure
39061-59-1 structure
Product Name:tert-Butyl 2-Chloro-2-oxoacetate
CAS No:39061-59-1
MF:C6H9ClO3
MW:164.586861371994
CID:292199
PubChem ID:11126621
Update Time:2025-05-20

tert-Butyl 2-Chloro-2-oxoacetate Chemical and Physical Properties

Names and Identifiers

    • Acetic acid, chlorooxo-, 1,1-dimethylethyl ester
    • tert- butyl 2-chloro-2-oxoacetate
    • tert-Butoxycarbonylcarbonyl chloride
    • TERT-BUTYL CHLORO(OXO)ACETATE
    • 39061-59-1
    • chloro-oxo-acetic acid t-butyl ester
    • tert-butyl2-chloro-2-oxoacetate
    • UDACWKHNECHEBB-UHFFFAOYSA-N
    • 2-chloro-2-oxo-acetic acid tert.butylester
    • AKOS025146393
    • tert-butyl 2-chloro-2-oxoacetate
    • EN300-101862
    • MFCD03788742
    • SCHEMBL836808
    • t-butyl 2-chloro-2-oxoacetate
    • DTXSID00456104
    • C77511
    • t-butyl chlorooxalate
    • BS-13359
    • tert-Butyl 2-Chloro-2-oxoacetate
    • MDL: MFCD03788742
    • Inchi: 1S/C6H9ClO3/c1-6(2,3)10-5(9)4(7)8/h1-3H3
    • InChI Key: UDACWKHNECHEBB-UHFFFAOYSA-N
    • SMILES: ClC(C(=O)OC(C)(C)C)=O

Computed Properties

  • Exact Mass: 164.02407
  • Monoisotopic Mass: 164.0240218g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 3
  • Complexity: 157
  • 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
  • XLogP3: 2
  • Topological Polar Surface Area: 43.4?2

Experimental Properties

  • PSA: 43.37

tert-Butyl 2-Chloro-2-oxoacetate Pricemore >>

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Additional information on tert-Butyl 2-Chloro-2-oxoacetate

tert-Butyl 2-Chloro-2-Oxoacetate: A Comprehensive Overview

tert-Butyl 2-Chloro-2-Oxoacetate, also known by its CAS number CAS No. 39061-59-1, is a versatile organic compound that has garnered significant attention in the fields of organic synthesis and pharmaceutical research. This compound, with the molecular formula C6H9ClO3, is characterized by its unique structure, which includes a tert-butyl group attached to a chloroketone moiety. Its chemical properties make it an invaluable intermediate in the synthesis of various bioactive molecules and pharmaceutical agents.

The structure of tert-butyl 2-chloro-2-oxoacetate consists of a central ketone group (C=O) flanked by a chlorine atom and a tert-butyl ester group. This configuration not only imparts stability to the molecule but also facilitates its reactivity in various chemical transformations. Recent studies have highlighted its role as a key intermediate in the synthesis of β-lactam antibiotics, where it serves as a precursor for the formation of critical intermediates.

One of the most notable applications of tert-butyl 2-chloro-2-oxoacetate is in the field of medicinal chemistry. Researchers have utilized this compound to develop novel inhibitors for enzymes such as β-lactamases, which are responsible for antibiotic resistance in bacteria. By incorporating this compound into drug design strategies, scientists aim to combat the growing threat of antibiotic resistance, a pressing issue in global healthcare.

In addition to its role in pharmaceutical research, tert-butyl 2-chloro-2-oxoacetate has found applications in agrochemicals and material science. For instance, it has been employed as an intermediate in the synthesis of herbicides and fungicides, contributing to advancements in crop protection technologies. Recent advancements in green chemistry have also led to the exploration of more sustainable methods for synthesizing this compound, reducing its environmental footprint while maintaining its high yield and purity.

The synthesis of tert-butyl 2-chloro-2-oxoacetate typically involves multi-step reactions that require precise control over reaction conditions. One common approach involves the chlorination of tert-butyl acetoacetate under specific conditions to introduce the chlorine atom at the α-position. This method has been optimized through recent studies to enhance selectivity and minimize by-products, ensuring a high-quality product suitable for downstream applications.

Recent research has also focused on understanding the reactivity and stability of tert-butyl 2-chloro-2-oxoacetate under various reaction conditions. For example, studies have demonstrated its ability to undergo nucleophilic acyl substitution reactions efficiently, making it an ideal substrate for constructing complex molecules with high functional group tolerance. These findings have expanded its utility in modern organic synthesis methodologies.

Beyond its chemical applications, tert-butyl 2-chloro-2-oxy acetate has also been studied for its potential in biotechnological processes. Researchers are exploring its use as a precursor for bio-based materials and sustainable polymers, aligning with global efforts to transition towards more eco-friendly industrial practices.

In conclusion, tert-butyl 2-chloro-2-oxy acetate, with its unique chemical properties and diverse applications, continues to be a focal point in contemporary research across multiple disciplines. Its role as an intermediate in drug development, agrochemicals, and advanced materials underscores its importance in driving innovation across industries. As scientific advancements continue to unfold, this compound is poised to contribute even more significantly to addressing some of the most pressing challenges in modern science.

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