Dibenzylphosphoryl chloride

• CAS: 538-37-4
• Catalog Number: ACM538374
• Category: Main Products
• Molecular Weight: 296.69
• Molecular Formula: C₁₄H₁₄ClO₃P
• Synonyms: CHLOROPHOSPHORIC ACID DIBENZYL ESTER;DIBENZYLPHOSPHORYL CHLORIDE;Dibenzylphosphoryl Chloride, [95%], in benzene - 10% w/v;dibenzyl phosphorochloridate;95%,inbenzene10%w/v;DBPCl;Dibenzyl chlorophosphonate;Dibenzyl=chlorophosphonate
• IUPAC Name: [chloro(phenylmethoxy)phosphoryl]oxymethylbenzene
• SMILES: C1=CC=C(C=C1)COP(=O)(OCC2=CC=CC=C2)Cl
• InChI Key: YADJFRGSGWGMNH-UHFFFAOYSA-N
• Boiling Point: 428.2ºC at 760mmHg
• Flash Point: 339.9ºC
• Density: 1.283
• Application: This product, Dibenzylphosphoryl chloride, is commonly used in solutions with inert solvents such as chloroform, carbon tetrachloride, benzene, and ether for the phosphorylation of nucleosides and amino acids. It is important to note that this product is shipped in a cooler to maintain its quality.
• Exact Mass: 296.03700
• Stability: Store in freezer at -20ºC

Case Study

Utilization of Dibenzylphosphoryl Chloride in the Synthesis of Indole Chalcone Derivatives

Yan, Jun, et al. Journal of medicinal chemistry, 2016, 59(11), 5264-5283.

Jun Yan, et al. synthesized 29 indole chalcone derivatives and evaluated their ability to inhibit cell proliferation. The antiproliferative analysis revealed compound 14k had the strongest activity among all tested indole chalcone derivatives. The compound showed minimal toxic effects on normal human cells but retained its effectiveness against drug-resistant cancer cells which suggests it could be used in cancer therapy. Compound 14k's solubility was improved through the introduction of phosphoramidate at its N position which created 14k-P.
Dibenzylphosphoryl chloride (22) played a crucial role as an intermediate in the synthesis of 14k-P. The synthesis process involved several steps: Initially, a mixture of dimethylaniline and benzyl alcohol was gradually added to a stirred and cooled solution of phosphorus trichloride dissolved in benzene, yielding dibenzyl phosphite (21). Subsequently, compound 21 was reacted with N-chlorosuccinimide to produce the intermediate dibenzylphosphoryl chloride (DBPCl, 22). Following this, compound 14k underwent phosphorylation with 22 in the presence of NaHMDS to create the N-phosphorylated derivative (23). The final deprotection of 23 and neutralization with NaOH resulted in the desired compound 14k-P.

Utilization of Dibenzylphosphoryl Chloride in the Synthesis of Ribosyl Pyrophosphate Derivatives

Gopinath, Purushothaman, et al. Proceedings of the National Academy of Sciences, 2015, 112(39), 12011-12014.

The synthesis of ribosyl pyrophosphate derivatives, key intermediates in nucleotide biosynthesis (catalyzed by enzymes and Mg2+), was investigated to explore their role in coupling ribose units with nucleophiles.
Within the synthetic pathway, dibenzylphosphoryl chloride (7) played an essential role, where compound 6 (dibenzylphosphonate) reacted with N-chlorosuccinimide to produce 7. This compound was then coupled with 2,3,5-tribenzoylribose 1-phosphate (5), resulting in the formation of ribosyl dibenzyl pyrophosphate (8). Following this, catalytic hydrogenation using Pd-C and triethylamine converted 8 into 2,3,5-tribenzoylribose 1-pyrophosphate (9).
To circumvent interference from benzoyl protecting groups during C-N bond formation studies, an alternative route synthesized 2,3,5-tris(phenylpropyl)-substituted ribose 1-pyrophosphate (19). Starting with D-ribose (11), methanol combined with catalytic H2SO4 yielded methyl ribofuranoside (12/14). Sodium hydride and phenylpropyl bromide (13) further reacted to form the tris-protected methyl ribofuranoside (14/15). STreatment with HBr-AcOH (16) converted 14 to ribosyl bromide 15, which reacted with dibenzyl phosphate (3) to form ribose-dibenzylphosphate (16). Reduction with Pd-C provided the protected ribose phosphate (17), and its coupling with 7 resulted in dibenzylpyrophosphate (18). The final hydrogenation of 18 led to the formation of phenylpropyl-substituted ribosyl pyrophosphate (19).