15074-54-1

Usage

Uses

Used in Oligonucleotide Synthesis:
2-Chlorophenyl phosphorodichloridate is used as a phosphorylating reagent for the synthesis of oligonucleotides via the triester method. This application is crucial in the development of various molecular biology techniques and the creation of synthetic genes and gene fragments.
Used in Monoand Oligonucleotide Preparation:
In the field of molecular biology, 2-chlorophenyl phosphorodichloridate is used as a reagent for the preparation of mononucleotide building blocks, which are essential components in the construction of oligonucleotides and oligonucleotide phosphorothioates. These molecules play a vital role in various research and therapeutic applications, such as gene regulation, drug discovery, and the development of novel diagnostic tools.
Used in Pharmaceutical Industry:
2-Chlorophenyl phosphorodichloridate is also utilized in the pharmaceutical industry for the synthesis of oligonucleotide-based drugs. These drugs have the potential to treat a wide range of diseases, including genetic disorders, viral infections, and cancer, by modulating gene expression or directly targeting specific molecular pathways.

InChI:InChI=1/C6H4Cl3O2P/c7-5-3-1-2-4-6(5)11-12(8,9)10/h1-4H

Upstream product

• 35535-81-0 sodium 2-chlorophenoxide 
• 10026-13-8 phosphorus pentachloride 
• 95-57-8 2-monochlorophenol 

Downstream Products

• 26507-20-0 2-(2-chloro-phenoxy)-[1,3,2]diazaphosphinane 2-oxide 
• 30203-59-9 O-ethyl-O-(2-chlorophenyl) chlorophosphate 
• 77244-72-5 2-Dibromomethyl-benzoic acid (2R,3R,4R,5R)-5-(6-benzoylamino-purin-9-yl)-4-[(2-chloro-phenoxy)-[1,2,4]triazol-1-yl-phosphinoyloxy]-2-(9-phenyl-9H-xanthen-9-yloxymethyl)-tetrahydro-furan-3-yl ester 
• 72351-28-1 2-chlorophenyl phosphordi(1H-1-[1,2,4]triazolide) 
• 125440-28-0 2-chlorophenyl bis(3'-O-acetylthymidin-5'-yl) phosphate 
• 81196-20-5 2-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl phosphate 
• 79258-44-9 5'-O-(9-phenylxanthen-9-yl)thymidine-3'-(2-chlorophenyl) phosphate 
• 112104-81-1 (1,2:4,6-Di-O-benzyliden-α-D-glucopyranose-3)-(2-chlorphenyl)-(triethylammonium)-phosphat 
• 112104-79-7 (1,2:3,5-Di-O-benzyliden-α-D-glucofuranose-6)-(2-chlorphenyl)-(triethylammonium)-phosphat 
• 134009-25-9 Phosphoric acid (2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester; compound with triethyl-amine 
• 127553-47-3 5'-O-DMTr-2'-O-TBDMS-uridine-3'-O-(2-chlorophenyl)phosphate triethylammonium salt 
• 133990-21-3 Phosphoric acid (2R,3R,4R,5R)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester; compound with triethyl-amine 
• 127578-31-8 5'-O-DMTr-2'-O-TBDMS-N-Bz-cytidine-3'-O-(2-chlorophenyl)phosphate triethylammonium salt 
• 132776-89-7 5'-O--5-<3-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-<1-<(1,1-di-methylethoxy)carbonyl>-1H-imidazol-4-yl>-1-oxopropyl>-amino>ethyl>amino>-3-oxopropyl>-2'-deoxyuridine 3'-(o-chlorophenyl phosphate) triethylamine 

Relevant academic research and scientific papers

Pd(II)-catalyzed ortho-arylation of aryl phosphates and aryl hydrogen phosphates with diaryliodonium triflates

Functionalized biaryl compounds were successfully synthesized using phosphates as the ortho-directing group in the Pd(II)/Pd(IV) catalytic cycle.

Hydrogen phosphates: Self initiated organocatalysts for the controlled ring-opening polymerization of cyclic esters

A series of arylhydrogenphosphates and aryldihydrogenphosphates was synthesized and characterized using spectroscopic methods and single crystal X-ray diffraction. These compounds were assessed as catalysts towards the ring-opening polymerization and proved to be potent organocatalysts for the ring-opening polymerization of cyclic esters. The bulk polymerizations were performed in the absence of external initiator. The polymerization proceeds in a controlled fashion which leads to well defined polyesters with narrow molecular weight distributions. In the post polymerization experiments, kinetics, mechanism and monomer concentration effects were investigated. The kinetic results have confirmed the pseudo-living character of the polymerizations and mechanistic studies suggest that the polymerization operates through a cationic mechanism.

New phosphoroamidate compounds: Synthesis, structural characterization and studies on ZnCl2 assisted hydrolysis of the P-N bond

A variety of phosphorodiamidate compounds were synthesized from the corresponding phosphorodichloridate intermediates and phosphorus oxychloride. These were completely characterized using different spectroscopic methods and single crystal X-ray diffraction studies on one of them. Studies revealed that water in the presence of a mild Lewis acid like ZnCl2 was found to assist the hydrolysis of the P-N linkage. The proof of this concept was effectively realized through the hydrolysis of hexamethylphosphoramide.

Anti-proliferative and anti-leukemic activity of DDE46 (compound WHI-07), a novel bromomethoxylated arylphosphate derivative of zidovudine, and related compounds: Studies using human acute lymphoblastic leukemia cells and the zebrafish model

The anti-proliferative effects of a novel bromomethoxylated arylphosphate derivative of zidovudine (compound DDE46, CAS 213982-96-8) were first examined in a zebra fish embryo model. DDE46 blocked the cell division at the 2-cell stage of the embryonic development followed by total cell fusion. DDE46 also inhibited the proliferation of the leukemic cell lines NALM-6 and MOLT-3. DDE46 enhanced the activity of the pro-apoptotic enzymes Caspase-3, Caspase-6, Caspase-8, and Caspase-9 leading to the apoptotic death of the leukemic cell line Jurkat. These results justify the further development of this agent as a new anti-leukemic drug candidate. ECV · Editio Cantor Verlag, Aulendorf (Germany).

Syntheses and spectral characterization of 2-aryloxy - 5,5′- bis(bromomethyl)-1,3,2P-dioxaphosphorinane 2-oxides

2-Aryloxy-5,5′-bis(bromomethyl)-1,3,2-dioxaphosphorinane 2-oxides 3 have been synthesized by the reaction of 2,2′-bis(bromomethyl)-1,3- propanediol 1 with various arvlphosphorodichloridates 2a-h in the presence of triethylamine in dry tetrahydrofuran at room temperatuure. Their 1H, 13C, 31P NMR and mass spectral data are discussed.

Synthesis of aryl dichlorophosphates using phase transfer catalysts

Synthesis of aryl dichlorophosphates has been carried out using phase transfer method.Two strategies, one involving solid-liquid and the other liquid-liquid phase transfer catalysts, have been used to synthesize phenyl, p-nitrophenyl and o-chlorophenyl phosphorodichloridates.In either case, the phenoxide ions are carried from the solid or aq. phase with the help of a phase transfer catalyst into the organic phase where the reaction with phosphoryl chloride occurs efficiently.A possible mechanism has been proposed.

Synthesis of potential UDP-glucuronosyltransferase inhibitors containing a diphosphate function

The synthesis of potential inhibitors of UDP-glucuronosyltransferase, in which the β-phosphate moiety of uridine 5'-diphosphate is linked to phenolic or alcoholic hydroxyl groups, is described.Key intermediates in the formation of the diphosphate function are S-(4-methylphenyl) 2-cyanoethyl phosphorothioate triesters which, after conversion into the corresponding S-(4-methylphenyl) phosphorothioate diesters, react with phosphate monoesters, in the presence of iodine, to give the target molecules.

Preparation of 3-substituted cephalosporins

There is described a process for preparing an enamine of formula (IX): STR1 where R2 is a carboxylic acid protecting group and R3 is the residue of a carboxylic acid derived acyl group and where R5 and R6 are the same or different C1-4 alkyl or C7-10 aralkyl groups; or taken together with the adjacent nitrogen atom form a heterocyclic ring containing from 4 to 8 carbon atoms and optionally a further heteroatom selected from oxygen and nitrogen; by reacting a compound of formula (XII): STR2 with an amine of formula HNR5 R6, the reactant of formula (XII) being prepared by reaction of an appropriate enol derivative with a phosphorus reagent. The enamines of formula (IX) are useful in the preparation of 3-hydroxycephalosporins.