16893-58-6

Basic information

• Product Name: benzyltriphenyphosphonium tetraphenylborate
• Synonyms: benzyltriphenyphosphonium tetraphenylborate;BENZYLTRIPHENYLPHOSPHONIUM TETRAPHENYLBORATE
• CAS NO: 16893-58-6
• Molecular Formula: C₂₄H₂₀B*C₂₅H₂₂P
• Molecular Weight: 672.642541
• Mol File: 16893-58-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: benzyltriphenyphosphonium tetraphenylborate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyltriphenyphosphonium tetraphenylborate(16893-58-6)
• EPA Substance Registry System: benzyltriphenyphosphonium tetraphenylborate(16893-58-6)

Safety Data

• Hazardous Substances Data: 16893-58-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Benzyltriphenyphosphonium tetraphenylborate is used as a phase transfer catalyst for facilitating the transfer of ions between immiscible solvents, which is crucial in various organic synthesis reactions.
Used in the Preparation of Phosphonium and Borate Compounds:
benzyltriphenyphosphonium tetraphenylborate serves as a reactant in the synthesis of other phosphonium and borate compounds, contributing to the development of new materials and chemical intermediates.
Used in Antimicrobial Applications:
Benzyltriphenyphosphonium tetraphenylborate has been investigated for its potential antimicrobial properties, indicating its possible use in applications where microbial control is necessary.
Used in Antitumor Research:
benzyltriphenyphosphonium tetraphenylborate has also been studied for its potential antitumor properties, suggesting a possible role in cancer research and therapeutic development.
It is important to handle benzyltriphenyphosphonium tetraphenylborate with care due to its strong irritant nature, ensuring proper storage and usage in well-ventilated areas.

Upstream product

• 143-66-8 sodium tetraphenyl borate 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 100-39-0 benzyl bromide 
• 1449-46-3 benzyltriphenylphosphonium bromide 

Relevant articles and documents

Wittig Olefination Using Phosphonium Tetraphenylborate in the Absence of Additional Base

The thermal decomposition of (substituted methyl)triphenylphosphonium tetraphenylborates, which can also be generated in situ from the corresponding phosphonium halide and NaBPh4, with an aldehyde affords olefins in 22-100% yields. This Wittig olefination does not need use additional base to form phosphorus ylide, and is highly tolerant of benzoic acid.

Ion-pairing of phosphonium salts in solution: C-H...halogen and C-H...π hydrogen bonds

The 1HNMR chemical shifts of the C(α)-H protons of arylmethyl triphenylphosphonium ions in CD2Cl2 solution strongly depend on the counteranions X-. The values for the benzhydryl derivatives Ph2CH-PPh3+ X -, for example, range from δH=8.25 (X -=Cl-) over 6.23 (X-=BF4 -) to 5.72ppm (X-=BPh4-). Similar, albeit weaker, counterion-induced shifts are observed for the ortho-protons of all aryl groups. Concentration-dependent NMR studies show that the large shifts result from the deshielding of the protons by the anions, which decreases in the order Cl- > Br- a‰ BF4 - > SbF6-. For the less bulky derivatives PhCH2-PPh3+ X-, we also find C-H...Ph interactions between C(α)-H and a phenyl group of the BPh4- anion, which result in upfield NMR chemical shifts of the C(α)-H protons. These interactions could also be observed in crystals of (p-CF3-C6H4)CH2-PPh 3+ BPh4-. However, the dominant effects causing the counterion-induced shifts in the NMR spectra are the C-H...X- hydrogen bonds between the phosphonium ion and anions, in particular Cl- or Br-. This observation contradicts earlier interpretations which assigned these shifts predominantly to the ring current of the BPh4- anions. The concentration dependence of the 1HNMR chemical shifts allowed us to determine the dissociation constants of the phosphonium salts in CD2Cl2 solution. The cation-anion interactions increase with the acidity of the C(α)-H protons and the basicity of the anion. The existence of C-H...X- hydrogen bonds between the cations and anions is confirmed by quantum chemical calculations of the ion pair structures, as well as by X-ray analyses of the crystals. The IR spectra of the Cl- and Br- salts in CD2Cl2 solution show strong red-shifts of the C-H stretch bands. The C-H stretch bands of the tetrafluoroborate salt PhCH 2-PPh3+ BF4- in CD 2Cl2, however, show a blue-shift compared to the corresponding BPh4- salt.

CH-Anion versus anion-π interactions in the crystal and in solution of pentafluorobenzyl phosphonium salts

A series of phosphonium salts with pentafluorobenzyl substituents have been synthesized and were investigated in the crystal as well as in solution. The solid state structures of 1a, 1b and 2d reveal the presence of anion-π as well as CH-anion interactions. The two attractive, yet competitive forces seem to act in concert and a directing effect of the CH interaction on the relative position between anion and π-system is observed. The search for anion-π interactions in solution failed. Only CH-anion interactions proved to be important in solution.