Cas no 98021-98-8 (oxolan-3-yl chloroformate)

Oxolan-3-yl chloroformate is a reactive chloroformate ester derived from tetrahydrofuran, primarily used as an intermediate in organic synthesis and pharmaceutical applications. Its key advantage lies in its ability to act as an efficient acylating agent, facilitating the introduction of the oxolan-3-yl carbonyl group into target molecules under mild conditions. The compound’s cyclic ether structure enhances reactivity while maintaining stability, making it suitable for selective derivatization of amines, alcohols, and other nucleophiles. Its utility extends to peptide coupling and polymer chemistry, where controlled functionalization is required. Proper handling under anhydrous conditions is recommended due to its moisture sensitivity.
oxolan-3-yl chloroformate structure
oxolan-3-yl chloroformate structure
Product Name:oxolan-3-yl chloroformate
CAS No:98021-98-8
MF:C5H7ClO3
MW:150.560281038284
MDL:MFCD24141282
CID:1989758
PubChem ID:15291007
Update Time:2025-06-08

oxolan-3-yl chloroformate Chemical and Physical Properties

Names and Identifiers

    • Carbonochloridic acid, tetrahydro-3-furanyl ester
    • oxolan-3-yl carbonochloridate
    • [(3S)-oxolan-3-yl] carbonochloridate
    • oxolan-3-yl chloroformate
    • SCHEMBL1622405
    • AKOS020233350
    • BULSKJQNVXVGHX-UHFFFAOYSA-N
    • DTXSID00571048
    • tetrahydrofuran-3-yl carbonochloridate
    • 3-tetrahydrofuranyl chloroformate
    • F2147-1344
    • DB-433721
    • Carbonochloridic acid, (3R)-tetrahydro-3-furanyl ester
    • tetrahydro-furan-3-yl chloroformate
    • tetrahydrofuran-3-ylcarbonochloridate
    • EN300-322657
    • G54196
    • 98021-98-8
    • tetrahydrofuran-3-yl chloridocarbonate
    • MDL: MFCD24141282
    • Inchi: 1S/C5H7ClO3/c6-5(7)9-4-1-2-8-3-4/h4H,1-3H2
    • InChI Key: BULSKJQNVXVGHX-UHFFFAOYSA-N
    • SMILES: ClC(=O)OC1COCC1

Computed Properties

  • Exact Mass: 150.0083718Da
  • Monoisotopic Mass: 150.0083718Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 2
  • Complexity: 115
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.2
  • Topological Polar Surface Area: 35.5?2

Experimental Properties

  • Density: 1.3±0.1 g/cm3
  • Boiling Point: 191.2±29.0 °C at 760 mmHg
  • Flash Point: 82.9±23.3 °C
  • Vapor Pressure: 0.5±0.4 mmHg at 25°C

oxolan-3-yl chloroformate Security Information

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Additional information on oxolan-3-yl chloroformate

Oxolan-3-yl Chloroformate (CAS No. 98021-98-8): An Overview of Its Properties, Applications, and Recent Research

Oxolan-3-yl chloroformate (CAS No. 98021-98-8) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, also known as 3-chloroformyloxolan, is characterized by its unique chemical structure, which includes a chloroformate functional group attached to a five-membered oxolan ring. The combination of these structural features endows the compound with a range of interesting properties and potential applications.

The chemical formula of oxolan-3-yl chloroformate is C6H7ClO3, and it has a molecular weight of approximately 154.57 g/mol. The compound is typically a colorless to pale yellow liquid at room temperature and is soluble in common organic solvents such as dichloromethane, ethyl acetate, and tetrahydrofuran (THF). Its physical and chemical properties make it an attractive candidate for various synthetic transformations and derivatizations.

In the realm of medicinal chemistry, oxolan-3-yl chloroformate has been explored for its potential as a building block in the synthesis of bioactive molecules. The chloroformate functional group can readily react with primary and secondary amines to form carbamates, which are important intermediates in the development of drugs targeting various therapeutic areas. For instance, carbamates have been used in the design of inhibitors for enzymes such as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), which are implicated in neurological disorders like Alzheimer's disease.

Recent research has also highlighted the utility of oxolan-3-yl chloroformate in the synthesis of prodrugs. Prodrugs are biologically inactive compounds that are converted into their active forms through metabolic processes within the body. The oxolan ring structure provides a stable platform for the attachment of various functional groups, allowing for the design of prodrugs with improved pharmacokinetic properties such as enhanced solubility, stability, and bioavailability. For example, a study published in the Journal of Medicinal Chemistry demonstrated that derivatives of oxolan-3-yl chloroformate could be used to enhance the oral bioavailability of poorly soluble drugs.

Beyond its applications in drug development, oxolan-3-yl chloroformate has found use in other areas of chemical research. In polymer science, it has been employed as a monomer or cross-linking agent in the synthesis of functional polymers with tailored properties. The ability to introduce both hydrophilic and hydrophobic functionalities through derivatization makes it a valuable tool for creating materials with specific performance characteristics. For instance, researchers at the University of California have utilized oxolan-3-yl chloroformate-based polymers to develop coatings with enhanced adhesion and durability.

The safety profile of oxolan-3-yl chloroformate is an important consideration in its use. While it is generally considered safe when handled properly under laboratory conditions, appropriate personal protective equipment (PPE) should be used to minimize exposure risks. It is important to follow standard safety guidelines for handling organic solvents and reactive chemicals to ensure safe laboratory practices.

In conclusion, oxolan-3-yl chloroformate (CAS No. 98021-98-8) is a multifaceted compound with significant potential in medicinal chemistry, pharmaceutical research, and polymer science. Its unique chemical structure and reactivity make it an attractive candidate for various synthetic applications, from drug development to materials science. As research continues to advance, it is likely that new applications and insights into the properties of this compound will emerge, further expanding its utility in diverse scientific fields.

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