1806-49-1

Usage

Uses

Used in Pharmaceutical Industry:
(ChloroMethyl)diphenylphosphine Oxide is used as a reagent for the production of peptide thioesters. These peptide thioesters are essential intermediates in the synthesis of various bioactive peptides and peptidomimetics, which have potential applications in drug development and therapeutics.
Additionally, (ChloroMethyl)diphenylphosphine Oxide is also used for the production of peptide thioesters in the context of analogous alkyl bromides. These alkyl bromides are valuable synthetic building blocks in organic chemistry, particularly for the synthesis of complex organic molecules and pharmaceutical compounds.

Upstream product

• 50-00-0 formaldehyd 
• 1079-66-9 chloro-diphenylphosphine 
• 1499-21-4 Diphenylphosphinic chloride 
• 100-58-3 phenylmagnesium bromide 
• 1983-26-2 chloromethylphosphonic dichloride 
• 593-71-5 Chloroiodomethane 
• 829-85-6 diphenylphosphane 
• 4559-70-0 Diphenylphosphine oxide 
• 57137-53-8 (chloromethyl)diphenylphosphane 
• 884-74-2 (diphenylphosphinoyl)methanol 

Downstream Products

• 13119-15-8 methylthiodiphenylphosphine oxide 
• 31238-57-0 diphenyl(phenylthiomethyl)phosphine oxide 
• 31238-56-9 C₂₀H₁₉OPS 
• 20920-23-4 methyltriphenylphosphonium perchlorate 
• 31238-55-8 diphenyl iodomethyl phosphine oxide 
• 23896-98-2 (Chlormethyl)bis-m-nitrophenylphosphin oxid 
• 69783-53-5 Methyl-diphenyl--phosphoniumchlorid 
• 2071-21-8 bis(diphenylphosphoryl)methane 
• 92465-86-6 1-(Diphenyl-phosphinoylmethoxy)-4-nitro-benzene 
• 95651-31-3 ethylene glycol mono<(diphenylphosphinyl)methyl> ether 
• 89302-50-1 C₁₃H₁₂OP 
• 89302-51-2 C₁₃H₁₁ClOP 
• 89302-49-8 C₁₃H₁₃ClOP^(1-) 

Relevant academic research and scientific papers

Direct and straightforward transfer of C1 functionalized synthons to phosphorous electrophiles for accessinggem-P-containing methanes

The direct transfer of different α-substituted methyllithium reagents to chlorinated phosphorous electrophiles of diverse oxidation state (phosphates, phosphine oxides and phosphines) is proposed as an effective strategy to synthesize geminal P-containing

Reduction of Tertiary Phosphine Oxides by BH 3 Assisted by Neighboring Activating Groups

Tertiary sulfanylphosphine and aminoalkylphosphine oxides can be easily converted into the corresponding tertiary sulfanylphosphine- and aminoalkylphosphine-boranes, respectively, through the facile P=O bond reduction by borane complexes. The easy reduction of the strong P=O bond by BH 3, a mild reducing agent, has been achieved through an intramolecular P=O - B complexation directed by proximal SH or NH activating groups located at the α- or β-position to the P=O bond. A generalized reduction mechanism has been proposed.

A Versatile Approach for Site-Specific Lysine Acylation in Proteins

Using amber suppression in coordination with a mutant pyrrolysyl-tRNA synthetase-tRNAPylpair, azidonorleucine is genetically encoded in E. coli. Its genetic incorporation followed by traceless Staudinger ligation with a phosphinothioester allows the convenient synthesis of a protein with a site-specifically installed lysine acylation. By simply changing the phosphinothioester identity, any lysine acylation type could be introduced. Using this approach, we demonstrated that both lysine acetylation and lysine succinylation can be installed selectively in ubiquitin and synthesized histone H3 with succinylation at its K4 position (H3K4su). Using an H3K4su-H4 tetramer as a substrate, we further confirmed that Sirt5 is an active histone desuccinylase. Lysine succinylation is a recently identified post-translational modification. The reported technique makes it possible to explicate regulatory functions of this modification in proteins.

A Photo-Triggered Traceless Staudinger–Bertozzi Ligation Reaction

The use of light to control the course of a chemical/biochemical reaction is an attractive idea because of its ease of administration with high precision and fine spatial resolution. Staudinger ligation is one of the commonly adopted conjugation processes that involve a spontaneous reaction between azides and arylphosphines to form iminophosphoranes, which further hydrolyze to give stable amides. We designed an anthracenylmethyl diphenylphosphinothioester (1) that showed promising Staudinger ligation reactivity upon photo-excitation. Broadband photolysis at 360–400 nm in aqueous organic solvents induced heterolytic cleavage of its anthracenylmethyl–phosphorus bond, releasing a diphenylphosphinothioester (2) as an efficient traceless Staudinger–Bertozzi ligation reagent. The quantum yield of such a photo-induced heterolytic bond-cleavage at the optimal wavelength of photolysis (376 nm) at room temperature is ≥0.07. This work demonstrated the feasibility of photocaging arylphosphines to realize the photo-triggering of the Staudinger ligation reaction.

Diarylphosphine- and dialkylphosphine-containing compounds, processes of preparing same and uses thereof as tridentate ligands

A novel process of preparing tridentate ligands containing one or more of a diarylphosphine and/or dialkylphosphine electron donating groups are disclosed. Use of this process for preparing a combinatorial library of such tridentate ligands and of organometallic complexes containing same is also disclosed. Further disclosed are novel diarylphosphine-containing and dialkylphosphine-containing compounds that can serve as tridentate ligands (e.g., pincer ligands), combinatorial libraries of such tridentate ligands, organometallic complexes containing these ligands (e.g., pincer complexes), and combinatorial libraries of such complexes. Methods utilizing these libraries for screening for candidate organometallic catalysts are also disclosed. Novel precursor molecules useful for preparing the tridentate ligands and processes of preparing same are also disclosed.

Staudinger ligation of peptides at non-glycyl residues

The Staudinger ligation provides a means to form an amide bond between a phosphinothioester and azide. This reaction holds promise for the ligation of peptides en route to the total chemical synthesis of proteins. (Diphenylphosphino)methanethiol is the mo

The synthesis of benzylphosphine oxidesvia vicarious nucleophilic substitution and alkenes via VNS-Horner-Wittig reactions

A range of substituted nitrobenzenes react with the anion of (chloromethyl)diphenylphosphinoyl oxide to give the substituted nitrobenzyldiphenylphosphine oxide by vicarious nucleophilic substitution. The novel stereoselective synthesis of E-stilbenes via a one-pot vicarious nucleophilic substitution-Horner-Wittig reaction is described.

High-yielding staudinger ligation of a phosphinothioester and azide to form a peptide

(eqution presented) The Staudinger ligation can be used to couple a peptide with a C-terminal phosphinothioester to another with an N-terminal α-azido group to form a single peptide that contains no residual atoms. Here, diphenylphosphinomethanethiol thio

The effect of the phosphoryl group on the rate and mechanism of SN-substitution at the saturated carbon atoms

The reactivity of diarylphosphine oxides RR'P(O)CH2X with p-O2NC6H4ONa in DMF have been studied.The reaction rate increases with the electrodrawing properties of the substituents on R and R' in the following way: p-Me2NC6H4 2 reaction rate of diphenylphosphine oxides has been investigated.The reactivity increases as follows Cl I Br OTs.A reaction mechanism is suggested.

PHOSPHANE OXIDES AS INTERMEDIATES IN THE SYNTHESIS OF POTENTIALLY BIOACTIVE COMPOUNDS

New chloromethylphosphane oxides, as well as phosphane oxide-substituted benzyl alcohols, benzaldehydes, aromatic nitro compounds, anilines, and phenols were synthesized as intermediates for the introduction of the phosphane oxide function into bioactive