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| | 4,4'-Dinitrodiphenic acid Basic information |
| Product Name: | 4,4'-Dinitrodiphenic acid | | Synonyms: | 4,4'-Dinitrodiphenic acid;4,4'-Dinitro-1,1'-biphenyl-2,2'-dicarboxylic acid;4,4'-Dinitro-2,2'-biphenyldicarboxylic acid;4,4'-Dinitro-2,2'-diphenic acid;[1,1'-Biphenyl]-2,2'-dicarboxylicacid, 4,4'-dinitro-;[1,1-Biphenyl]-2,2-dicarboxylicacid, 4,4-dinitro->99%;4-Dinitrodiphenic acid;4,4'-Dinitrodiphenic acid (Stellar-2020) [Under Development] | | CAS: | 20246-81-5 | | MF: | C14H8N2O8 | | MW: | 332.22 | | EINECS: | | | Product Categories: | | | Mol File: | 20246-81-5.mol |  |
| | 4,4'-Dinitrodiphenic acid Chemical Properties |
| Melting point | 258-259℃ | | Boiling point | 539.5±50.0 °C(Predicted) | | density | 1.632 | | storage temp. | Sealed in dry,Room Temperature | | pka | 2.61±0.22(Predicted) | | Appearance | White to off-white Solid | | InChI | InChI=1S/C14H8N2O8/c17-13(18)11-5-7(15(21)22)1-3-9(11)10-4-2-8(16(23)24)6-12(10)14(19)20/h1-6H,(H,17,18)(H,19,20) | | InChIKey | CDYUHLLQUAYYHD-UHFFFAOYSA-N | | SMILES | C1(C2=CC=C([N+]([O-])=O)C=C2C(O)=O)=CC=C([N+]([O-])=O)C=C1C(O)=O |
| RIDADR | UN1325 | | HazardClass | 4.1 |
| | 4,4'-Dinitrodiphenic acid Usage And Synthesis |
| Synthesis | General procedure for the synthesis of 4,4'-dinitro-1,1'-biphenyl-2,2'-dicarboxylic acid (DNBPDC) from the compound (CAS: 863305-32-2): 12.1 g of DPA (diphenylacetylene) was dissolved in 75 mL of concentrated sulfuric acid, and 25 mL of fuming nitric acid was slowly added at a temperature of less than 50 °C. The reaction was completed by stirring for 10 minutes. After addition, the reaction mixture was continued to be stirred for 10 minutes, followed by a rapid temperature increase to 60 °C, and the reaction was maintained at this temperature for 2 hours. Upon completion of the reaction, the mixture was carefully poured into a small amount of crushed ice. After a few hours, the resulting light yellow solid was collected by filtration, washed with water and dried at 60 °C to give 14.2 g DNBPDC. the product has a melting point of 236 °C (decomposition). The compound is insoluble in ether, chloroform and cold water, but soluble in ethanol and DMF.When recrystallized from DMF at high temperature, very fine needle-like crystals were obtained. Elemental analysis results (calculated value, C16H15N3O8): C, 50.93%; H, 4.01%; N, 11.14%. Measured values: C, 50.90%; H, 3.99%; N, 11.05%. Infrared spectra (IR) characteristic absorption peaks: νas(CO2-) 1709 (s) cm-1, νs(NO2) 1344 (s) cm-1, νas(NO2) 1533 (m) cm-1. | | References | [1] Patent: WO2013/50121, 2013, A1. Location in patent: Page/Page column 82; 83
[2] Patent: WO2013/50122, 2013, A1. Location in patent: Page/Page column 99
[3] Journal of the American Chemical Society, 2001, vol. 123, # 24, p. 5768 - 5776
[4] Justus Liebigs Annalen der Chemie, 1878, vol. 193, p. 131
[5] Organic Letters, 2007, vol. 9, # 2, p. 235 - 238 |
| | 4,4'-Dinitrodiphenic acid Preparation Products And Raw materials |
| Raw materials | [1,1'-Biphenyl]-2,2'-dicarboxylic acid, (1R)- (9CI)-->4,4'-Dinitro-2,2'-dicarbonylbiphenyl-->2,7-Dinitro-9,10-phenanthrenedione-->BIPHENYL-2,2'-DICARBOXALDEHYDE-->[1,1'-Biphenyl]-2,2'-dicarboxylicacid, 4,4'-dinitro-, 2,2'-diMethyl ester-->Methyl 2-iodo-5-nitrobenzoate-->2-BROMO-5-NITROBENZOIC ACID-->Methyl 2-bromo-5-nitrobenzoate-->3-(N,N-DIMETHYLAMINO)ANILINE-->Sulfuric acid-->1-Iodonaphthalene-->2-Chloro-5-nitrobenzoic acid-->3-Nitrobenzoic acid-->Phenanthrene |
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