Bis(p-nitrophenyl) phosphate

Bis(p-nitrophenyl) phosphate
Names
	IUPAC name Bis(4-nitrophenyl) hydrogen phosphate
	Other names Phosphoric acid, bis(4-nitrophenyl) ester; Phosphoric acid, bis(p-nitrophenyl) ester; Di-p-nitrophenyl phosphate; BNPP; Bis-PNPP;
Identifiers
CAS Number	645-15-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:3122;
ChEMBL	ChEMBL1231178;
ChemSpider	250;
DrugBank	DB07418;
ECHA InfoCard	100.010.396
EC Number	211-434-7;
KEGG	C03779;
PubChem CID	255;
UNII	1MF77LEI63;
CompTox Dashboard (EPA)	DTXSID20870742 ;
	InChI InChI=1S/C12H9N2O8P/c15-13(16)9-1-5-11(6-2-9)21-23(19,20)22-12-7-3-10(4-8-12)14(17)18/h1-8H,(H,19,20) Key: MHSVUSZEHNVFKW-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1[N+](=O)[O-])OP(=O)(O)OC2=CC=C(C=C2)[N+](=O)[O-];
Properties
Chemical formula	C12H9N2O8P
Molar mass	340.184 g·mol−1
Melting point	175 °C (347 °F; 448 K)
Acidity (pKa)	1.04 (predicted)
Conjugate base	(C6H4NO2)2PO−4
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300
Precautionary statements	P264, P270, P301+P310+P330, P405, P501
Safety data sheet (SDS)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bis(p-nitrophenyl) phosphate or BNPP is an organophosphate. It is an enzyme inhibitor for carboxylesterase^[1] and glycosyltransferases,^[2] and a model compound for the hydrolysis of DNA by phosphodiesterases.^[3] The neutral compound has the chemical formula (C₆H₄NO₂)₂PO₃OH; at physiological pH, it exists as the conjugate base (C₆H₄NO₂)₂PO−4.

Applications

BNPP is used as a substitute for DNA to study the enzymatic hydrolysis of phosphodiesters, and to evaluate synthetic enzyme mimics. While the compound was first synthesised in the 1950s or 1960s, it only became widely used beginning in the 1990s. It has several advantages as a model compound for this reaction: it reacts more quickly than many natural phosphodiesters, and the leaving group, nitrophenol, is readily identified using spectrophotometry.^[3]

Sources

↑ Kolassa, Norbert; Tuisl, Elisabeth; Kraupp, Otto (1977). "Effects of the carboxylesterase inhibitor bis-(p-nitrophenyl)-phosphate on disposition and metabolism of hexobendine". Biochemical Pharmacology. 26 (3): 223–228. doi:10.1016/0006-2952(77)90307-0. PMID 843391.
↑ Guette, Frédérique; Cacan, René; Montreuil, Jean; Verbert, André (1983). "Inhibition of glycosyltransferases by bis-(p-nitrophenyl)phosphate: General effect and relation to their membrane integration". Biochimie. 65 (10): 563–567. doi:10.1016/s0300-9084(83)80106-0. PMID 6228260.
1 2 Casnati, Alessandro; Salvio, Riccardo (2025). "An equal terms comparison of the proficiency of artificial phosphodiesterases by using simple models of RNA or DNA as benchmarks–the takeaway to design next generation supramolecular catalysts". Coordination Chemistry Reviews. 531 216479. doi:10.1016/j.ccr.2025.216479. hdl:2108/408643.

[1] Kolassa, Norbert; Tuisl, Elisabeth; Kraupp, Otto (1977). "Effects of the carboxylesterase inhibitor bis-(p-nitrophenyl)-phosphate on disposition and metabolism of hexobendine". Biochemical Pharmacology. 26 (3): 223–228. doi:10.1016/0006-2952(77)90307-0. PMID 843391.

[2] Guette, Frédérique; Cacan, René; Montreuil, Jean; Verbert, André (1983). "Inhibition of glycosyltransferases by bis-(p-nitrophenyl)phosphate: General effect and relation to their membrane integration". Biochimie. 65 (10): 563–567. doi:10.1016/s0300-9084(83)80106-0. PMID 6228260.

[casnati_et_al-3] 1 2 Casnati, Alessandro; Salvio, Riccardo (2025). "An equal terms comparison of the proficiency of artificial phosphodiesterases by using simple models of RNA or DNA as benchmarks–the takeaway to design next generation supramolecular catalysts". Coordination Chemistry Reviews. 531 216479. doi:10.1016/j.ccr.2025.216479. hdl:2108/408643.

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