777-52-6

Basic information

• Product Name: 4-NITROPHENYL PHOSPHORODICHLORIDATE
• Synonyms: phosphorodichloridicacid,4-nitrophenylester;4-nitrophenyl dichlorophosphonate;4-Nitrophenylphosphorodichloridate,97%;Dichloridophosphoric acid p-nitrophenyl;Dichloridophosphoric acid p-nitrophenyl ester;Dichlorophosphinic acid=p-nitrophenyl ester;Dichloridophosphoric Acid P-Nitrop;1-dichlorophosphoryloxy-4-nitrobenzene
• CAS NO: 777-52-6
• Molecular Formula: C₆H₄Cl₂NO₄P
• Molecular Weight: 255.98
• EINECS: 212-289-2
• Mol File: 777-52-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 44-45 °C(lit.)
• Boiling Point: 182-183 °C13 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /solid
• Density: 1.644
• Vapor Pressure: 0.000342mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: 2-8°C
• BRN: 1468239
• CAS DataBase Reference: 4-NITROPHENYL PHOSPHORODICHLORIDATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROPHENYL PHOSPHORODICHLORIDATE(777-52-6)
• EPA Substance Registry System: 4-NITROPHENYL PHOSPHORODICHLORIDATE(777-52-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 777-52-6(Hazardous Substances Data)

Usage

Uses

4-Nitrophenyl phosphorodichloridate was used to phosphorylate the derivatized resin.

Application

4-Nitrophenyl Phosphorodichloridate is used as a reagent in the synthesis of dihydrobenzodioxaphosphocine oxide derivatives which have antioxidant activity.

InChI:InChI=1/C6H4Cl2NO4P/c7-14(8,12)13-6-3-1-5(2-4-6)9(10)11/h1-4H

Upstream product

• 100-02-7 4-nitro-phenol 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 824-78-2 4-nitrophenol sodium salt 

Downstream Products

• 26315-44-6 bis-aziridin-1-yl-phosphinic acid-(4-nitro-phenyl ester) 
• 950-35-6 methyl paraoxon 
• 311-45-5 paraoxon 
• 60886-35-3 phosphoric acid diisopentyl ester-(4-nitro-phenyl ester) 
• 7284-47-1 phosphoric acid diisobutyl ester-(4-nitro-phenyl ester) 
• 3254-66-8 phosphoric acid diisopropyl ester-(4-nitro-phenyl ester) 
• 16562-50-8 thymidine 3'-O-(4-nitrophenyl)phosphate 
• 54113-53-0 Phosphoramidic acid methyl ester 4-nitro-phenyl ester 
• 54638-64-1 Phosphoric acid 4-nitro-phenyl ester bis-(2,2,2-trichloro-1-methoxy-ethyl) ester 
• 68521-35-7 6-(4-nitro-phenoxy)-6,7-dihydro-5H-dibenzo[d,f][1,3,2]diazaphosphepine 6-oxide 
• 71771-35-2 2-p-nitrophenoxy-2-oxo-trans-5,6-tetramethylene-1,3,2-oxazaphosphorinane 
• 5297-73-4 Methyl-(4-nitro-phenyl)-N-cyclohexyl-phosphoramidat 
• 70545-01-6 p-nitrophenyl phosphoethanolamine 
• 79838-05-4 4-nitrophenyl-4-morpholinylphosphonochloridate 

Relevant articles and documents

Catalytic signal amplification for the discrimination of ATP and ADP using functionalised gold nanoparticles

Diagnostic assays that incorporate a signal amplification mechanism permit the detection of analytes with enhanced selectivity. Herein, we report a gold nanoparticle-based chemical system able to differentiate ATP from ADP by means of catalytic signal amplification. The discrimination between ATP and ADP is of relevance for the development of universal assays for the detection of enzymes which consume ATP. For example, protein kinases are a class of enzymes critical for the regulation of cellular functions, and act to modulate the activity of other proteins by transphosphorylation, transferring a phosphate group from ATP to give ADP as a byproduct. The system described here exploits the ability of cooperative catalytic head groups on gold nanoparticles to very efficiently catalyze chromogenic reactions such as the transphosphorylation of 2-hydroxypropyl-4-nitrophenyl phosphate (HPNPP). A series of chromogenic substrates have been synthesized and evaluated by means of Michaelis-Menten kinetics (compounds 2, 4-6). 2-Hydroxypropyl-(3-trifluoromethyl-4-nitro)phenyl phosphate (5) was found to display higher reactivity (kcat) and higher binding affinity (KM) when compared to HPNPP. This higher binding affinity allows phosphate 5 to compete with ATP and ADP to different extents for binding on the monolayer surface, thus enabling a catalytically amplified signal only when ATP is absent. Overall, this represents a viable new approach for monitoring the conversion of ATP into ADP with high sensitivity.

Application of phosphoramidate ProTide technology significantly improves antiviral potency of carbocyclic adenosine derivatives

We report the application of phosphoramidate pronucleotide (ProTide) technology to the antiviral agent carbocyclic L-d4A (L-Cd4A). The phenyl methyl alaninyl parent ProTide of L-Cd4A was prepared by Grignard-mediated phosphorochloridate reaction and resulted in a compound with significantly improved anti-HIV (2600-fold) and HBV activity. We describe modifications of the aryl, ester, and amino acid regions of the ProTide and how these changes affect antiviral activity and metabolic stability. Separate and distinct SARs were noted for HIV and HBV. Additionally, ProTides were prepared from the D-nucleoside D-Cd4A and the dideoxy analogues L-CddA and D-CddA. These compounds showed more modest potency improvements over the parent drug. In conclusion, the ProTide approach is highly successful when applied to L-Cd4A with potency improvements in vitro as high as 9000-fold against HIV. With a view to preclinical candidate selection we carried out metabolic stability studies using cynomolgus monkey liver and intestinal S9 fractions.