1560-54-9 Usage
Description
Allyltriphenylphosphonium bromide is a white crystalline powder that belongs to the class of phosphonium salts. It is a versatile reagent with a wide range of applications in various chemical reactions and industries.
Uses
1. Antiviral Applications:
Allyltriphenylphosphonium bromide is used as an antiviral agent for its activity against influenza virus A. It plays a crucial role in the development of new antiviral treatments and strategies to combat viral infections.
2. Wittig Olefination:
Used in Organic Chemistry:
Allyltriphenylphosphonium bromide is used as a reagent for the Wittig olefination of aldehydes, which is a widely employed method for the preparation of conjugated dienes. This reaction is essential in the synthesis of various organic compounds and pharmaceuticals.
3. Preparation of DES:
Used in the Pharmaceutical Industry:
Allyltriphenylphosphonium bromide is used as a reactant for the preparation of a diol and carbamate chemistry library for common functional groups. It is also utilized in the synthesis of deep eutectic solvents (DES), which are environmentally friendly alternatives to traditional solvents.
4. Regioselective Synthesis of Alkenes:
Used in Chemical Synthesis:
Allyltriphenylphosphonium bromide is used as a reactant for the regioselective synthesis of alkenes via semihydrogenation and semihydrogenation-oxidation of dienes. This process is vital for the production of specific alkene isomers with desired properties.
5. Alkene Addition of Frustrated Lewis Pairs:
Used in Organometallic Chemistry:
Allyltriphenylphosphonium bromide is used as a reactant in the alkene addition of frustrated Lewis pairs, which are important in the development of new catalytic systems and the synthesis of complex organic molecules.
6. Olefination of N-Sulfonyl Imines:
Used in Stereoselective Synthesis:
Allyltriphenylphosphonium bromide is used as a reagent for the olefination of N-sulfonyl imines, which is a key step in the stereoselective synthesis of vinyl arenes. This reaction is crucial for the production of chiral compounds with specific configurations.
7. Tandem Michael Addition / Ylide Olefination:
Used in Advanced Synthesis:
Allyltriphenylphosphonium bromide is used as a reactant in tandem Michael addition/ylide olefination reactions, which are employed for the synthesis of highly functionalized cyclohexadienes. These reactions are essential for the preparation of complex organic molecules with multiple functional groups.
8. Reaction with Garner's Aldehyde:
Used in Organic Synthesis:
The reaction of allyltriphenylphosphonium bromide and Garner's aldehyde in basic media provides β-hydroxy-1,3-dienes, which are valuable intermediates in the synthesis of various organic compounds.
Preparation
Allyltriphenylphosphonium bromide was synthesized from the reaction of triphenylphosphine and allyl bromide in dry toluene.
Check Digit Verification of cas no
The CAS Registry Mumber 1560-54-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,6 and 0 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1560-54:
(6*1)+(5*5)+(4*6)+(3*0)+(2*5)+(1*4)=69
69 % 10 = 9
So 1560-54-9 is a valid CAS Registry Number.
InChI:InChI=1/C21H20P/c1-2-18-22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21/h2-17H,1,18H2/q+1
1560-54-9Relevant articles and documents
Supramolecular Recognition of Quaternary Phosphonium Cations
Walsh, Mark P.,Kitching, Matthew O.
, (2021/12/06)
The modes of supramolecular recognition of quaternary phosphonium cations mediated by 1,1′-bi-2-naphthol (BINOL) are identified and characterized. In contrast to our previous work on ammonium cations, the recognition of the quaternary phosphonium cations via the formation of a PR4+·Br–·BINOL ternary complex was found to be mediated by a hydrogen bond from an α-carbon center of the phosphonium cation, encapsulation within a continuous hydrogen bond network between the halide–BINOL network, or a combination of these effects working in tandem. The solid state structures of these ternary complexes were analyzed by X-ray crystallography, aided by Hirshfeld surface analysis, to confirm the presence of characteristic intermolecular interactions for the identified modes. In all cases, the quaternary phosphonium cation acts as a hydrogen bond donor (HBD) in these supramolecular interactions, and thus this is the key to the recognition process with BINOL. The characterization of such mechanisms offers insight into the supramolecular and crystal engineering communities in the future design of agents capable of the supramolecular recognition of phosphonium cations and their abstraction from the solution phase.
Cascade 8πElectrocyclization/Benzannulation to Access Highly Substituted Phenylpyridines
Du, Luan,Gong, Yiliang,Han, Jingpeng,Li, Baosheng,Li, You,Luo, Han,Tian, Yi,Xin, Xiaolan
supporting information, p. 7966 - 7971 (2021/10/25)
A cascade 8πelectrocyclization/benzannulation reaction was developed to obtain the synthetically important highly substituted phenyl-pyridines. This method shows great potential in the rapid and inexpensive application of the scalable and operationally simple production of accessible substrates. On the basis of the resulting phenyl-pyridine products, a new Ru catalyst and bidentate ligand were designed and prepared, further demonstrating its high practicability.
Radical-Mediated Heck-Type Alkylation: Stereoconvergent Synthesis of Functionalized Polyenes
Zhang, Hong,Wu, Xinxin,Wei, Yunlong,Zhu, Chen
supporting information, p. 7568 - 7572 (2019/10/02)
The stereospecific synthesis of polyenes is of great synthetic value. Disclosed herein is a new, efficient, stereoconvergent approach for the synthesis of functionalized polyenes via a radical-mediated Heck-type alkylation. The easily accessed Z- and E-mixed alkenes are harnessed as starting material, leading to a unique stereoisomer of polyenes. In addition, the transformation features mild reaction conditions and broad functional group compatibility. A variety of valuable 1,3-dienes and 1,3,5-trienes are afforded in useful yields.