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20246-81-5

20246-81-5 Structure

20246-81-5 Structure
IdentificationBack Directory
[Name]

4,4'-Dinitrodiphenic acid
[CAS]

20246-81-5
[Synonyms]

4-Dinitrodiphenic acid
4,4'-Dinitrodiphenic acid
4,4'-Dinitro-2,2'-diphenic acid
4,4'-Dinitro-2,2'-biphenyldicarboxylic acid
4,4'-Dinitro-1,1'-biphenyl-2,2'-dicarboxylic acid
[1,1'-Biphenyl]-2,2'-dicarboxylicacid, 4,4'-dinitro-
[1,1-Biphenyl]-2,2-dicarboxylicacid, 4,4-dinitro->99%
[Molecular Formula]

C14H8N2O8
[MDL Number]

MFCD21337356
[MOL File]

20246-81-5.mol
[Molecular Weight]

332.22
Chemical PropertiesBack Directory
[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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[RIDADR ]

UN1325
[HazardClass ]

4.1
Spectrum DetailBack Directory
[Spectrum Detail]

4,4'-Dinitrodiphenic acid(20246-81-5)1HNMR
Hazard InformationBack Directory
[Synthesis]

[1,1'-Biphenyl]-2,2'-dicarboxylic acid, (1R)- (9CI)

863305-32-2

4,4'-Dinitrodiphenic acid

20246-81-5

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
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