Cas no 22651-87-2 (Cyclohexanecarboxylic anhydride)

Cyclohexanecarboxylic anhydride is a cyclic anhydride derived from cyclohexanecarboxylic acid, commonly used as an intermediate in organic synthesis and polymer chemistry. Its key advantages include high reactivity as an acylating agent, making it valuable in the production of esters, amides, and other derivatives. The cyclic structure enhances thermal stability, allowing for use in high-temperature applications. It is also employed in the synthesis of specialty chemicals, pharmaceuticals, and coatings due to its ability to introduce cyclohexyl functionalities. The anhydride's low volatility and solid form at room temperature facilitate handling and storage. Its compatibility with various reagents and solvents further broadens its utility in industrial and laboratory settings.
Cyclohexanecarboxylic anhydride structure
22651-87-2 structure
Product Name:Cyclohexanecarboxylic anhydride
CAS No:22651-87-2
MF:C14H22O3
MW:238.322684764862
MDL:MFCD12404944
CID:284637
PubChem ID:253659566
Update Time:2025-06-08

Cyclohexanecarboxylic anhydride Chemical and Physical Properties

Names and Identifiers

    • Cyclohexanecarboxylicacid, 1,1'-anhydride
    • Cyclohexanecarboxylic Anhydride
    • cyclohexanecarbonyl cyclohexanecarboxylate
    • CYCLOHEXANECARBOXYLIC ACID ANHYDRIDE
    • Cyclohexancarbonsaeure-anhydrid
    • EINECS 245-146-8
    • Cyclohexanecarboxylic acid, anhydride
    • NSC75109
    • cyclohexane carboxylic anhydride
    • Bis(cyclohexanecarboxylic)anhydride
    • JOHUAELJNSBTGS-UHFFFAOYSA-N
    • MFCD12404944
    • NS00027237
    • AKOS025396908
    • DTXSID90177194
    • A925523
    • NSC 75109
    • CHZ4DJ2FT2
    • SCHEMBL248821
    • NSC-75109
    • C2735
    • 22651-87-2
    • E76387
    • CYCLOHEXANECARBOXYLIC ACID, 1,1'-ANHYDRIDE
    • SY051256
    • CS-0155338
    • UNII-CHZ4DJ2FT2
    • cyclohexanecarboxylicanhydride
    • DTXCID2099685
    • Cyclohexanecarboxylic anhydride
    • MDL: MFCD12404944
    • Inchi: 1S/C14H22O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h11-12H,1-10H2
    • InChI Key: JOHUAELJNSBTGS-UHFFFAOYSA-N
    • SMILES: O(C(C1CCCCC1)=O)C(C1CCCCC1)=O

Computed Properties

  • Exact Mass: 238.15700
  • Monoisotopic Mass: 238.15689456g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 4
  • Complexity: 245
  • 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: 43.4
  • XLogP3: 4.1

Experimental Properties

  • Boiling Point: 156°C/0.7mmHg(lit.)
  • Refractive Index: 1.4740-1.4780
  • PSA: 43.37000
  • LogP: 3.21680

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Cyclohexanecarboxylic anhydride Production Method

Cyclohexanecarboxylic anhydride Related Literature

Additional information on Cyclohexanecarboxylic anhydride

Recent Advances in the Application of Cyclohexanecarboxylic Anhydride (CAS: 22651-87-2) in Chemical Biology and Pharmaceutical Research

Cyclohexanecarboxylic anhydride (CAS: 22651-87-2) is a cyclic anhydride derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound, characterized by its unique reactivity and structural properties, has been employed in various synthetic and medicinal chemistry applications, including drug design, peptide modification, and polymer synthesis. Recent studies have explored its potential as a key intermediate in the development of novel therapeutic agents and biomaterials, highlighting its importance in advancing the field.

One of the most notable applications of cyclohexanecarboxylic anhydride is its role in the synthesis of peptide-based therapeutics. Researchers have utilized its reactivity to introduce cyclohexyl groups into peptide backbones, thereby enhancing the stability and bioavailability of peptide drugs. A 2023 study published in the Journal of Medicinal Chemistry demonstrated the successful incorporation of cyclohexanecarboxylic anhydride into cyclic peptides, resulting in improved pharmacokinetic properties and resistance to enzymatic degradation. This breakthrough has opened new avenues for the development of peptide-based drugs targeting complex diseases such as cancer and autoimmune disorders.

In addition to its applications in peptide chemistry, cyclohexanecarboxylic anhydride has also been investigated for its potential in polymer science. Recent research has shown that this compound can serve as a cross-linking agent in the synthesis of biodegradable polymers with tunable mechanical and thermal properties. A 2024 study in Biomacromolecules reported the development of a novel polymer network using cyclohexanecarboxylic anhydride, which exhibited exceptional biocompatibility and controlled degradation rates. These findings suggest promising applications in drug delivery systems and tissue engineering scaffolds.

Furthermore, the pharmaceutical industry has explored the use of cyclohexanecarboxylic anhydride as a building block for small-molecule drug candidates. Its ability to form stable covalent bonds with nucleophilic groups makes it a valuable tool for the design of prodrugs and targeted therapeutics. For instance, a recent study in ACS Chemical Biology highlighted the use of this anhydride in the development of a prodrug system for the controlled release of anti-inflammatory agents, demonstrating enhanced efficacy and reduced side effects in preclinical models.

Despite these advancements, challenges remain in the large-scale production and application of cyclohexanecarboxylic anhydride. Issues such as reagent stability, reaction selectivity, and environmental impact require further investigation. However, ongoing research efforts are addressing these limitations, with a focus on optimizing synthetic protocols and exploring greener alternatives. The continued exploration of this compound's potential is expected to yield significant contributions to the fields of chemical biology and pharmaceutical sciences in the coming years.

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