Dinitrobisphenol A

Dinitrobisphenol A
Names
	IUPAC name 2,2'-Dinitro-4,4'-(propane-2,2-di-yl)diphenol],
	Other names 3,3'-Dinitro-bisphenol A; 4,4'-Propane-2,2-diylbis(2-nitrophenol); Dinitro-bisphenol A; 2,2-Bis(4-hydroxy-3-nitrophenyl)propane; 4-[2-(4-Hydroxy-3-nitrophenyl)propan-2-yl]-2-nitrophenol
Identifiers
CAS Number	5329-21-5;
3D model (JSmol)	Interactive image;
ChemSpider	190706;
PubChem CID	219958;
CompTox Dashboard (EPA)	DTXSID40277355 ;
	SMILES CC(C)(C1=CC(=C(C=C1)O)[N+](=O)[O-])C2=CC(=C(C=C2)O)[N+](=O)[O-];
Properties
Chemical formula	C15H14N2O6
Molar mass	318.285 g·mol−1
Appearance	Yellow powder
Melting point	130 °C (266 °F; 403 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

3,3'-Dinitrobisphenol A is an organic compound with the formula (HO(O₂N)C₆H₃)₂C(CH₃)₂. It is a yellow-orange solid prepared by nitration of bisphenol A [1][1][2]

Carcinogenicity

3,3'-Dinitrobisphenol A is found to be genotoxic in male ICR mice on a micronucleus test.[3] Its estrogenic potential is not known however shown some binding to estrogen-related receptor gamma to an extent.[4]

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References

Sulzberg, Theodore; Cotter, Robert J. (1969). "Synthesis and polymerization of a dinitrobisphenol a: A new polycarbonate synthesis". Journal of Polymer Science Part B: Polymer Letters. 7 (3): 185. Bibcode:1969JPoSL...7..185S. doi:10.1002/pol.1969.110070303.
Babu, Sainath; Pathak, Chintan; Uppu, Satvika; Jones, Conrad; Fronczek, Frank R.; Uppu, Rao M. (2011). "3,3′-Dinitrobisphenol A". Acta Crystallographica Section E. 67 (10): o2556. doi:10.1107/S1600536811035458. PMC 3201564. PMID 22065402.
Toyoizumi, Tomoyasu; Deguchi, Yuya; Masuda, Shuichi; Kinae, Naohide (2014). "Genotoxicity and Estrogenic Activity of 3,3′-Dinitrobisphenol a in Goldfish". Bioscience, Biotechnology, and Biochemistry. 72 (8): 2118. doi:10.1271/bbb.80193.
Babu, Sainath; Vellore, Nadeem A.; Kasibotla, Agasthya V.; Dwayne, Harlan J.; Stubblefield, Michael A.; Uppu, Rao M. (2012). "Molecular docking of bisphenol a and its nitrated and chlorinated metabolites onto human estrogen-related receptor-gamma". Biochemical and Biophysical Research Communications. 426 (2): 215. doi:10.1016/j.bbrc.2012.08.065. PMID 22935422.

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[Sulzberg-1] Sulzberg, Theodore; Cotter, Robert J. (1969). "Synthesis and polymerization of a dinitrobisphenol a: A new polycarbonate synthesis". Journal of Polymer Science Part B: Polymer Letters. 7 (3): 185. Bibcode:1969JPoSL...7..185S. doi:10.1002/pol.1969.110070303.

[Babu-2] Babu, Sainath; Pathak, Chintan; Uppu, Satvika; Jones, Conrad; Fronczek, Frank R.; Uppu, Rao M. (2011). "3,3′-Dinitrobisphenol A". Acta Crystallographica Section E. 67 (10): o2556. doi:10.1107/S1600536811035458. PMC 3201564. PMID 22065402.

[Toyoizumi-3] Toyoizumi, Tomoyasu; Deguchi, Yuya; Masuda, Shuichi; Kinae, Naohide (2014). "Genotoxicity and Estrogenic Activity of 3,3′-Dinitrobisphenol a in Goldfish". Bioscience, Biotechnology, and Biochemistry. 72 (8): 2118. doi:10.1271/bbb.80193.

[BabuS-4] Babu, Sainath; Vellore, Nadeem A.; Kasibotla, Agasthya V.; Dwayne, Harlan J.; Stubblefield, Michael A.; Uppu, Rao M. (2012). "Molecular docking of bisphenol a and its nitrated and chlorinated metabolites onto human estrogen-related receptor-gamma". Biochemical and Biophysical Research Communications. 426 (2): 215. doi:10.1016/j.bbrc.2012.08.065. PMID 22935422.