51044-12-3

Basic information

• Product Name: (4-chlorobenzyl)(triphenyl)phosphonium bromide
• Synonyms: (4-Chlorobenzyl)(triphenyl)phosphonium bromide
• CAS NO: 51044-12-3
• Molecular Formula: Br*C₂₅H₂₁ClP
• Molecular Weight: 467.765
• Mol File: 51044-12-3.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (4-chlorobenzyl)(triphenyl)phosphonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: (4-chlorobenzyl)(triphenyl)phosphonium bromide(51044-12-3)
• EPA Substance Registry System: (4-chlorobenzyl)(triphenyl)phosphonium bromide(51044-12-3)

Safety Data

• Hazardous Substances Data: 51044-12-3(Hazardous Substances Data)

Upstream product

• 622-95-7 4-chlorobenzyl bromide 
• 603-35-0 triphenylphosphine 
• 104-88-1 4-chlorobenzaldehyde 
• 6399-81-1 triphenylphosphine hydrobromide 
• 873-76-7 para-Chlorobenzyl alcohol 
• 106-43-4 para-chlorotoluene 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 

Downstream Products

• 14064-55-2 (E)-4-chloro-4'-nitrostilbene 
• 51791-17-4 2-(4-chloro-phenyl)-1-[1,2,4]oxadiazol-3-yl-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 
• 82203-89-2 α-(trifluoroacetyl)-p-chlorobenzylidenetriphenylphosphorane 
• 79926-89-9 trans-1-(4-chlorophenyl)-2-(1-pyrenyl)ethene 
• 344593-36-8 cis-1-(4-chlorophenyl)-2-(1-pyrenyl)ethene 
• 52792-14-0 (E)-4-(4-chlorostyryl)-1,2-dimethoxybenzene 
• 52792-17-3 (α-benzoyl-α-4-chlorophenylmethylene)triphenylphosphorane 
• 5043-91-4 (E)-4-chloro-4'-methoxystilbene 
• 52792-16-2 (E,E)-1,4-bis(4-chlorostyryl)-benzene 
• 62103-03-1 4-(4-chloro-trans-styryl)-3-(4-methoxy-phenyl)-sydnone 
• 62103-02-0 4-(4-chloro-cis-styryl)-3-(4-methoxy-phenyl)-sydnone 
• 62102-95-8 4-(4-chloro-trans-styryl)-3-methyl-sydnone 
• 62102-94-7 4-(4-chloro-cis-styryl)-3-methyl-sydnone 
• 37985-13-0 (1E,3E)-1-chloro-4-(4-phenylbuta-1,3-dien-1-yl)benzene 

Relevant articles and documents

Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.

Synthesis and anti-inflammatory activity of phenylbutenoid dimer analogs

Several phenylbutenoid dimer (PBD) analogs were synthesized and evaluated for their inhibitory activities against nitric oxide (NO) production and TNF-α release. The PBD analogs were synthesized via Diels - Alder and subsequent Schlosser reactions as key steps. Among the tested compounds, two analogs (8c, 8f) exhibited much stronger inhibitory activity against LPS-stimulated NO production and TNF-α release in RAW 264.7 cells than that of wogonin.

Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes

A new simple and efficient method for the synthesis of 2-phenylnaphthalenes from electron-rich 1-styryl-2-methoxybenzenes has been described. The reaction proceeds via TFA catalyzed C-C bond cleavage followed by intermolecular [4+2]-Diels-Alder cycloaddition of an in situ formed styrenyl trifluoroacetate intermediate. The quantum chemical calculations identified the transition state for the cycloaddition reaction and helped in tracing the reaction mechanism. The method has been efficiently utilized for synthesis of the phenanthrene skeleton and a naphthalene-based potent and selective ER-β agonist. This journal is