1100-88-5 Usage
Description
Benzyltriphenylphosphonium chloride is a quaternary phosphonium salt that appears as a white to off-white powder. It is highly soluble in water and polarizable solvents, making it a versatile compound for various applications in organic synthesis.
Uses
Used in Organic Synthesis:
Benzyltriphenylphosphonium chloride is used as a reagent for the synthesis of stabilized phosphonium ylides containing saturated oxygen heterocycles. It is also utilized in the synthesis of novel substituted cis-stilbene derivatives, which exhibit antimicrobial activity.
Used in Pharmaceutical Applications:
Benzyltriphenylphosphonium chloride serves as a reactant for the synthesis of achiral N-hydroxyformamide inhibitors of ADAM-TS4 and ADAM-TS5, which are potential treatments for osteoarthritis.
Used in Material Science:
In the material science industry, benzyltriphenylphosphonium chloride is used as a crosslinking agent for tube-like natural halloysite/fluoroelastomer nanocomposites, enhancing the properties of these materials for various applications.
Used in Platinum Complex Synthesis:
Benzyltriphenylphosphonium chloride is used as a reactant for the synthesis of platinum chloro-tetrazole complexes via azidation, which are important in the field of coordination chemistry and catalysis.
Used in Wittig Olefination:
Benzyltriphenylphosphonium chloride is employed as a reactant in the Wittig olefination process to synthesize trans-stilbenes and cinnamates, which are valuable intermediates in the pharmaceutical and chemical industries.
Used in Light-Driven Molecular Brakes:
Benzyltriphenylphosphonium chloride is used as a reactant for the synthesis of pentiptycenes, which are utilized as light-driven molecular brakes in the development of molecular machines and switches.
Used in Petroleum Industry:
In the petroleum industry, benzyltriphenylphosphonium chloride is used as a reactant for the formation of archipelago structures for the production of petroleum asphaltenes, which are essential for the construction and road paving industries.
Used as a Phase Transfer Catalyst:
Benzyltriphenylphosphonium chloride is also used as a phase transfer catalyst in the production of fluoroelastomers and printing inks, facilitating the transfer of reactants between different phases and improving the efficiency of these processes.
Flammability and Explosibility
Notclassified
Purification Methods
Wash it with Et2O and crystallise it from EtOH (six-sided plates). It is hygroscopic and forms crystals with one molecule of H2O. [Michaelis & Soden Justus Liebigs Ann Chem 229 320 1885, Kr.hnke Chem Ber 83 291 1950, Beilstein 16 IV 994.]
Check Digit Verification of cas no
The CAS Registry Mumber 1100-88-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,0 and 0 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1100-88:
(6*1)+(5*1)+(4*0)+(3*0)+(2*8)+(1*8)=35
35 % 10 = 5
So 1100-88-5 is a valid CAS Registry Number.
InChI:InChI=1/C25H22P.ClH/c1-5-13-22(14-6-1)21-26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1
1100-88-5Relevant articles and documents
Stereospecific on-Surface Cyclodehydrogenation of Bishelicenes: Preservation of Handedness from Helical to Planar Chirality
Irziqat, Bahaaeddin,Cebrat, Aleksandra,Baljozovi?, Milo?,Martin, Kévin,Parschau, Manfred,Avarvari, Narcis,Ernst, Karl-Heinz
, p. 13523 - 13526 (2021)
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Grayson,M.,Keough,P.T.
, p. 3919 - 3924 (1960)
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Arylmethyloxyphenyl derivatives: Small molecules displaying P-glycoprotein inhibition
Colabufo, Nicola Antonio,Berardi, Francesco,Perrone, Roberto,Rapposelli, Simona,Digiacomo, Maria,Balsamo, Aldo
, p. 6607 - 6613 (2006)
Some arylmethyloxyphenyl derivatives were prepared as simplified structures of analogous arylpiperazines with high affinity toward dopaminergic D 2 and serotonergic 5-HT1A receptors and inhibiting P-glycoprotein (P-gp). The compounds 5b and 8b displayed good P-gp inhibition activity measured as [3H]vinblastine transport inhibition in the Caco-2 cell monolayer and intracellular doxorubicin accumulation in MCF7/Adr cells by flow cytometry. Compounds 5b and 8b also inhibited, dose-dependently, ATP-ase activation induced by P-gp substrate vinblastine.
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Wittig,G.,Schlosser,M.
, p. 1023 - 1028 (1962)
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Structure-Activity-Relationship-Aided Design and Synthesis of xCT Antiporter Inhibitors
Cirillo, Davide,Sarowar, Shahin,?yvind Enger, Per,Bj?rsvik, Hans-René
, p. 2650 - 2668 (2021/06/01)
The xCT antiporter is a cell membrane protein involved in active counter-transportation of glutamate (outflux) with cystine (influx) over the human cell membrane. This feature makes the xCT antiporter a crucial element of the biosynthesis of the vital free radical scavenger glutathione. The prodrug sulfasalazine, a medication for the treatment of ulcerative colitis, was previously proven to inhibit the xCT antiporter. Starting from sulfasalazine, a molecular scaffold jumping followed by SAR-assisted design and synthesis provided a series of styryl hydroxy-benzoic acid analogues that were biologically tested in vitro for their ability to decrease intracellular glutathione levels using four different cancer cell lines: A172 (glioma), A375 (melanoma), U87 (glioma) and MCF7 (breast carcinoma). Depletion of glutathione levels varied among the compounds as well as among the cell lines. Flow cytometry using propidium iodide and the annexin V marker demonstrated minimal toxicity in normal human astrocytes for a promising candidate molecule (E)-5-(2-([1,1′-biphenyl]-4-yl)vinyl)-2-hydroxybenzoic acid.