32597-92-5

Usage

Uses

Used in Organic Synthesis:
(3-Chlorobenzyl)triphenylphosphonium chloride is used as a phase transfer catalyst to facilitate the transfer of reactants from one phase to another, particularly in reactions involving organic and aqueous phases. It enhances the solubility of reactants in a different phase, which in turn increases the efficiency and yield of the reaction.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3-Chlorobenzyl)triphenylphosphonium chloride is used as a catalyst to improve the synthesis of various drugs. Its ability to act as a phase transfer catalyst allows for more efficient production processes and can lead to higher quality end products.
Used in Chemical Research:
(3-Chlorobenzyl)triphenylphosphonium chloride is also utilized in chemical research for studying reaction mechanisms and developing new synthetic methods. Its unique properties as a phase transfer catalyst make it a valuable tool for chemists working on complex organic reactions.

InChI:InChI=1/C25H21ClP/c26-22-12-10-11-21(19-22)20-27(23-13-4-1-5-14-23,24-15-6-2-7-16-24)25-17-8-3-9-18-25/h1-19H,20H2/q+1

Upstream product

• 603-35-0 triphenylphosphine 
• 620-20-2 1-Chloro-3-chloromethyl-benzene 

Downstream Products

• 75840-91-4 5-[(Z)-2-(3-Chloro-phenyl)-vinyl]-1H-imidazole 
• 75840-92-5 5-[(E)-2-(3-Chloro-phenyl)-vinyl]-1H-imidazole 
• 86983-58-6 (E)-1-chloro-3-(3-methyl-3-phenylbut-1-en-1-yl)benzene 
• 1011029-55-2 (E)-2-[2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid 
• 878801-20-8 [(benzylsulfonyl)(3-chlorophenyl)methylene](triphenyl)phosphorane 

Relevant academic research and scientific papers

Development of Novel Inhibitors for Histone Methyltransferase SET7/9 based on Cyproheptadine

The histone methyltransferase SET7/9 methylates not only histone but also non-histone proteins as substrates, and therefore, SET7/9 inhibitors are considered candidates for the treatment of diseases. Previously, our group identified cyproheptadine, used clinically as a serotonin receptor antagonist and histamine receptor (H1) antagonist, as a novel scaffold of the SET7/9 inhibitor. In this work, we focused on dibenzosuberene as a substructure of cyproheptadine and synthesized derivatives with various functional groups. Among them, the compound bearing a 2-hydroxy group showed the most potent activity. On the other hand, a 3-hydroxy group or another hydrophilic functional group such as acetamide decreased the activity. Structural analysis clarified a rationale for the improved potency only by tightly restricted location and type of the hydrophilic group. In addition, a SET7/9 loop, which was only partially visible in the complex with cyproheptadine, became more clearly visible in the complex with 2-hydroxycyproheptadine. These results are expected to be helpful for further structure-based development of SET7/9 inhibitors.

Synthesis of novel sulfonyl-stabilized phosphorus ylides, and the kinetics and mechanism of their conventional and flash vacuum pyrolysis reactions

Nine substituted sulfonyl-stabilized phosphorus ylides were prepared by treating their intermediate ylide analogues with phenylmethanesulfonyl fluoride. The stoichiometric ratio of the reactants for each preparation needed to be adjusted according to the basicity of each ylide intermediate. The nine ylide compounds were then subjected to conventional (sealed-tube) gas-phase pyrolysis at 470-545 K. The pyrolytic reactions were homogeneous and obeyed a first-order rate equation. The values of the Arrhenius log A (s-1) and E a (kJ mol-1) obtained for these reactions averaged 11.12 ± 2.00 and 131.8 ± 24.4, respectively. Analysis of the pyrolysates from conventional pyrolysis and from flash vacuum pyrolysis at 600 K showed the products to be complex mixtures of triphenylphosphine, triphenylphosphine oxide, triphenylphosphine sulfide, and symmetric and unsymmetric alkenes. Conventional pyrolysis also gave novel mixed sulfones and, for the p-methoxyaryl substituent, p-anisaldehyde. The products of the reactions under study are explained on the basis of a mechanism involving a sulfonyl carbene intermediate, and the reaction mechanism is used to rationalize the kinetic results and molecular reactivities.

Kinetic Study of the Substitution Reactions of Triphenylphosphine with Chlorobenzyl Chlorides, Dimethylbenzyl Chloride, and Methylbenzyl Bromides in Various Two-Phase Organic Solvent/Water Media

The kinetics of the substitution reactions of triphenylphosphine (TP) with chlorobenzyl chlorides (CBC), 2,5-dimethylbenzyl chloride (DMBC), and methylbenzyl bromides (MBB) in aprotic organic solvent was studied under the extraction by water. The effects of water, agitation, organic solvent, reactant, and temperature were investigated. These reactions take place via the SN2 mechanism and exhibit large and negative entropy of activation. The order of relative activity of solvents is CHCl3 > CH2Cl2 >> C6H6. In CHCl3, the order of relative reactivity of benzyl chloride (BC), benzyl bromide (BB), CBC, DMBC, and MBB toward reaction with TP is 2-MBB > 4-MBB > 3-MBB > BB > DMBC > BC > 2-CBC > 4-CBC > 3-CBC. These reactions produce quantitatively benzyltriphenylphosphonium salts, which are useful for synthesizing Z-form isomers of stilbenes via the two-phase Wittig reaction.

Synthesis and Photocylization of some 4-(5)Arylethenylimidazoles

The synthesis of eleven 4-(5)arylethenylimidazoles and their separation into cis and trans isomers is described.Ir, uv, nmr, and mass spectrometric data of the compounds are given.The photocyclization of the unsubstituted and p-substituted compounds is reported.