Cas no 82358-61-0 (Tributyl(cyanomethyl)phosphonium Chloride)

Tributyl(cyanomethyl)phosphonium chloride is a quaternary phosphonium salt with the molecular formula C??H??ClNP. This compound is primarily utilized as a versatile reagent in organic synthesis, particularly in phase-transfer catalysis and nucleophilic substitution reactions. Its phosphonium center and cyanomethyl functional group enhance reactivity, making it effective for the preparation of nitriles and other intermediates. The compound exhibits good solubility in polar organic solvents, facilitating homogeneous reaction conditions. Its stability under typical reaction conditions and efficient catalytic properties make it a valuable tool in pharmaceutical and fine chemical synthesis. Proper handling is required due to its hygroscopic nature and potential irritancy.
Tributyl(cyanomethyl)phosphonium Chloride structure
82358-61-0 structure
Product Name:Tributyl(cyanomethyl)phosphonium Chloride
CAS No:82358-61-0
MF:C14H29ClNP
MW:277.813524007797
MDL:MFCD00671508
CID:729234
PubChem ID:87566443
Update Time:2025-09-27

Tributyl(cyanomethyl)phosphonium Chloride Chemical and Physical Properties

Names and Identifiers

    • Phosphonium,tributyl(cyanomethyl)-, chloride (1:1)
    • Tributyl(cyanomethyl)phosphonium Chloride
    • tributyl(cyanomethyl)phosphanium,chloride
    • (Cyanomethyl)tributylphosphonium Chloride
    • Phosphonium, tributyl(cyanomethyl)-, chloride (9CI)
    • (Cyanomethyl)tributylphosphoniumchloride
    • C 1442
    • NSC 41943
    • MFCD00671508
    • SCHEMBL5145658
    • SY043125
    • CS-0037541
    • 82358-61-0
    • NSC41943
    • Cyanomethyltri-n-butylphosphonium chloride
    • EN300-7372770
    • C14H29ClNP
    • NSC-41943
    • tributyl(cyanomethyl)phosphanium chloride
    • Tributyl(cyanomethyl)phosphanium;chloride
    • A927994
    • W10650
    • AKOS015833117
    • DTXSID30469166
    • MDL: MFCD00671508
    • Inchi: 1S/C14H29NP.ClH/c1-4-7-11-16(14-10-15,12-8-5-2)13-9-6-3;/h4-9,11-14H2,1-3H3;1H/q+1;/p-1
    • InChI Key: JCHWNYYARSRCKZ-UHFFFAOYSA-M
    • SMILES: [Cl-].N#CC[P+](CCCC)(CCCC)CCCC

Computed Properties

  • Exact Mass: 277.17300
  • Monoisotopic Mass: 277.1726146g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 10
  • Complexity: 182
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 23.8?2

Experimental Properties

  • Color/Form: Not determined
  • Melting Point: 97.0 to 101.0 deg-C
  • Boiling Point: No data available
  • Flash Point: No data available
  • PSA: 37.38000
  • LogP: 1.93188
  • Solubility: Not determined
  • Vapor Pressure: No data available

Tributyl(cyanomethyl)phosphonium Chloride Security Information

Tributyl(cyanomethyl)phosphonium Chloride Pricemore >>

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Tributyl(cyanomethyl)phosphonium Chloride Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Nitromethane ;  15 min, < 50 °C; 16 h, rt
Reference
A Convenient Method for the Asymmetric Synthesis of Fluorinated α-Amino Acids from Alcohols
Drouet, Fleur; et al, European Journal of Organic Chemistry, 2014, 2014(6), 1195-1201

Production Method 2

Reaction Conditions
1.1 Solvents: Nitromethane ;  > 50 °C; 16 h, rt
Reference
Preparation of (Cyanomethylene)tributylphosphorane: A new Mitsunobu-type reagent
Sakamoto, Izumi; et al, Chemical & Pharmaceutical Bulletin, 2005, 53(11), 1508-1509

Production Method 3

Reaction Conditions
1.1 Solvents: Nitromethane
Reference
New Narwedine and Galanthamine Derivatives as Potential Alzheimer Therapeutics
Welzig, Stefan, 1997, , ,

Tributyl(cyanomethyl)phosphonium Chloride Raw materials

Tributyl(cyanomethyl)phosphonium Chloride Preparation Products

Additional information on Tributyl(cyanomethyl)phosphonium Chloride

Recent Advances in the Application of Tributyl(cyanomethyl)phosphonium Chloride (CAS: 82358-61-0) in Chemical Biology and Pharmaceutical Research

Tributyl(cyanomethyl)phosphonium Chloride (CAS: 82358-61-0) is a versatile organophosphorus compound that has garnered significant attention in recent years due to its unique chemical properties and potential applications in chemical biology and pharmaceutical research. This research briefing aims to provide an overview of the latest advancements in the utilization of this compound, focusing on its role as a key intermediate in organic synthesis, its biological activities, and its emerging applications in drug discovery and development.

Recent studies have highlighted the importance of Tributyl(cyanomethyl)phosphonium Chloride as a precursor in the synthesis of various biologically active molecules. Its ability to act as a phosphonium ylide precursor has been exploited in the construction of complex molecular architectures, including heterocyclic compounds and functionalized alkenes. A 2023 study published in the Journal of Organic Chemistry demonstrated its efficacy in facilitating the Wittig reaction under mild conditions, yielding high-purity products with excellent stereoselectivity.

In the realm of chemical biology, researchers have explored the compound's potential as a protein modification reagent. The phosphonium moiety's unique reactivity allows for selective labeling of cysteine residues in proteins, enabling the study of protein-protein interactions and post-translational modifications. A recent Nature Chemical Biology paper (2024) reported the development of a novel probe based on Tributyl(cyanomethyl)phosphonium Chloride for real-time monitoring of enzymatic activity in live cells.

Pharmaceutical applications of this compound have expanded significantly, particularly in the development of kinase inhibitors and antimicrobial agents. Its structural features make it an attractive scaffold for designing small molecule modulators of various biological targets. A 2024 study in the European Journal of Medicinal Chemistry described a series of novel anticancer agents derived from Tributyl(cyanomethyl)phosphonium Chloride derivatives, showing promising activity against multiple cancer cell lines with improved selectivity profiles.

The safety profile and pharmacokinetic properties of Tributyl(cyanomethyl)phosphonium Chloride derivatives have been the subject of recent investigations. While the parent compound shows moderate cytotoxicity, structural modifications have been shown to significantly improve biocompatibility. Current research efforts are focused on optimizing the compound's properties for in vivo applications, with particular attention to reducing off-target effects and improving metabolic stability.

Looking forward, the unique chemical properties of Tributyl(cyanomethyl)phosphonium Chloride continue to inspire innovative applications across multiple disciplines. Its combination of synthetic versatility and biological activity makes it a valuable tool for both fundamental research and applied pharmaceutical development. Future research directions may include exploring its potential in targeted drug delivery systems and as a component of novel biomaterials for medical applications.

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