Dibenzyl phosphite

Base Information

• Chemical Name: Dibenzyl phosphite
• CAS No.: 17176-77-1
• Molecular Formula: C14H15O3P
• Molecular Weight: 262.245
• Hs Code.: 29209090
• European Community (EC) Number: 241-226-1
• UNII: 1O720L5H5A
• DSSTox Substance ID: DTXSID20938038
• Wikidata: Q27252680
• Mol file: 17176-77-1.mol

Synonyms:Dibenzyl phosphite;Dibenzyl phosphonate;17176-77-1;Phosphonic acid dibenzyl ester;oxo-bis(phenylmethoxy)phosphanium;Phosphonic acid, bis(phenylmethyl) ester;MFCD00004774;Phosphonic Acid Bis(phenylmethyl) Ester;UNII-1O720L5H5A;1O720L5H5A;EINECS 241-226-1;Dibenzylphosphit;C14H15O3P;dibenzylphosphonate;SCHEMBL36370;Bis(benzyloxy)(oxo)phosphanium;DIBENZYL PHOSPHITE [MI];DTXSID20938038;MIBXHGZAARWAGI-UHFFFAOYSA-N;Dibenzyl phosphite, technical grade;C14-H15-O3-P;AKOS015964514;CS-W010143;s11959;AS-57330;SY010379;P1016;EN300-80532;Q-200957;Q27252680

Chemical Property of Dibenzyl phosphite

Chemical Property:

• Appearance/Colour: Clear colorless to yellow liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 0 to 5°
• Refractive Index: n20/D 1.555(lit.)
• Boiling Point: 435.3 °C at 760 mmHg
• Flash Point: 217 °C
• PSA: 59.00000
• Density: 1.187 g/mL at 25 °C(lit.)
• LogP: 3.80970
• Storage Temp.: 2-8°C
• Sensitive.: Air & Moisture Sensitive
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in DMSO, Methanol. Reacts with water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 261.06805630
• Heavy Atom Count: 18
• Complexity: 221

Purity/Quality:

99% ^*data from raw suppliers

Dibenzyl phosphite ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CO[P+](=O)OCC2=CC=CC=C2
• Uses: Dibenzyl Phosphite is used in the preparation of phenylalkylphosphonamidates which are then used as probes for a hydrophobic binding register in prostate-specific membrane antigen. In preparation of N-phosphorylated amines. Dibenzyl phosphite is used for the phosphorylation of phenols involves reaction in the presence of N-ethyldiisopropylamine and DMAP to give the dibenzyl phenyl phosphate. It is used in the preparation of phenylalkylphosphonamidates which are then used as probes for a hydrophobic binding register in prostate-specific membrane antigen.

Technology Process of Dibenzyl phosphite

There total 19 articles about Dibenzyl phosphite which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

benzyl alcohol (100-51-6,185532-71-2) → Dibenzyl phosphite (17176-77-1)

Guidance literature:

With N,N-dimethyl-aniline; phosphorus trichloride; In toluene; at 20 ℃; for 1h;

DOI:10.1055/s-2007-990811

Reference yield: 95.0%

→ {2-[5-(3,5-dichloro-phenylsulfanyl)-4-isopropyl-1-pyridin-4-ylmethyl-1H-imidazol-ylmethoxycarbonylamino]-ethyl}-phosphonic acid diphenyl ester + Dibenzyl phosphite (17176-77-1)

Guidance literature:

Reference yield: 95.0%

→ {2-[5-(3,5-dichloro-phenylsulfanyl)-4-isopropyl-1-pyridin-4-ylmethyl-1H-imidazol-2-ylmethoxycarbonylamino]-ethyl}-phosphonic acid diphenyl ester + Dibenzyl phosphite (17176-77-1)

Guidance literature:

upstream raw materials:

phenyldiazomethane

tribenzyl phosphite

triethylamine

N,N-diethylaniline

Downstream raw materials:

benzyl phosphite

N-benzyl-N-methylmorpholinium chloride

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

dibenzyl phosphochloridate

Refernces

Carbon-14 radiosynthesis of combretastatin A-1 (CA1) and its corresponding phosphate prodrug (CA1P)

10.1002/JLCR.1676

The research focuses on the carbon-14 radiosynthesis of combretastatin A-1 (CA1) and its phosphate prodrug CA1P, which are derived from the African bush willow tree and have significant medicinal value due to their ability to inhibit tubulin assembly and act as vascular disrupting agents in cancer treatment. The study details a four-step synthesis process to incorporate carbon-14 into CA1 and CA1P with high specific activity. Key reactants include the CA1 precursor, [14C]methyl iodide for radiolabeling, TiCl4 for deprotection, and dibenzyl phosphite for phosphorylation. The methodology involves methylation of the C-4 protected phenolic moiety, de-isopropylation with TiCl4, and conversion to the phosphate prodrug. Analyses were performed using 1H NMR, analytical HPLC, and radio-TLC to ensure chemical and radiochemical purities, with the final product achieving a specific activity of 55 mCi/mmol.