15074-54-1

Basic information

• Product Name: 2-CHLOROPHENYL PHOSPHORODICHLORIDATE
• Synonyms: 2-CHLOROPHENYL PHOSPHORODICHLORIDATE;2-CHLOROPHENYLPHOSPHORYL DICHLORIDE;2-CHLOROPHENYL DICHLOROPHOSPATE;2-CHLOROPHENYL DICHLOROPHOSPHATE;(2-Chlorophenyl)phosphoric acid dichloride;2-Chlorophenyl dichloridophosphate;o-Chlorophenylphosphonyl dichloride;Phosphorodichloridic acid, 2-chlorophenyl ester
• CAS NO: 15074-54-1
• Molecular Formula: C₆H₄Cl₃O₂P
• Molecular Weight: 245.43
• EINECS: 239-129-4
• Product Categories: Biochemistry;Nucleosides, Nucleotides & Related Reagents;Phosphorylating and Phosphorothioating Agents;Phosphorylation;Protecting Agents, Phosphorylating Agents & Condensing Agents;Synthetic Organic Chemistry;Building Blocks;Chemical Synthesis;Organic Building Blocks;Phosphorus Compounds;Phosphorus Halides
• Mol File: 15074-54-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 135-137 °C12 mm Hg(lit.)
• Flash Point: 221 °F
• Appearance: Colorless liquid
• Density: 1.491 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0113mmHg at 25°C
• Refractive Index: n20/D 1.538(lit.)
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 911009
• CAS DataBase Reference: 2-CHLOROPHENYL PHOSPHORODICHLORIDATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROPHENYL PHOSPHORODICHLORIDATE(15074-54-1)
• EPA Substance Registry System: 2-CHLOROPHENYL PHOSPHORODICHLORIDATE(15074-54-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 9
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 15074-54-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 15074-54-1 differently. You can refer to the following data:
1. Phosphorylating reagent for oligonucleotide synthesis via the triester method.1
2. 2-Chlorophenyl phosphorodichloridate has been used in the preparation of:mononucleotide building blocksoligonucleotides and oligonucleotide phosphorothioates in solution

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

Upstream product

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

Downstream Products

• 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) 
• 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 
• 134009-27-1 Phosphoric acid (2R,3R,4R,5R)-2-(6-benzoylamino-purin-9-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 
• 127553-42-8 5'-O-DMTr-2'-O-TBDMS-N-Bz-adenosine-3'-O-(2-chlorophenyl)phosphate triethylammonium salt 
• 136136-29-3 1-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl>-5-<<2,2,6,6-tetramethyl-1-(oxyl)piperidin-4-yl>amino>pyrimidine-2,4(1H,3H)-dione 3'<(2-chlorophenyl) triethylammonium phosphate> 
• 77451-39-9 2-Dibromomethyl-benzoic acid (2R,3R,4R,5R)-3-[(2-chloro-phenoxy)-hydroxy-phosphoryloxy]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-ylmethyl ester; compound with triethyl-amine 

Relevant articles and documents

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.

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.

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.