479-22-1

Basic information

• Product Name: NITRANILIC ACID
• Synonyms: NITRANILIC ACID;2,5-DIHYDROXY-3,6-DINITRO-1,4-BENZOQUINONE;2,5-DIHYDROXY-3,6-DINITROQUINONE;Nitranilic Acid Hexahydrate;2,5-Dihydroxy-3,6-dinitro-2,5-cyclohexadiene-1,4-dione;2,5-Dihydroxy-3,6-dinitro-p-benzoquinone;2,5-Dinitro-3,6-dihydroxy-1,4-benzoquinone;3,6-Dinitro-2,5-dihydroxy-1,4-benzoquinone
• CAS NO: 479-22-1
• Molecular Formula: C₆H₂N₂O₈
• Molecular Weight: 230.09
• Mol File: 479-22-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 170°C (rough estimate)
• Boiling Point: 372.06°C (rough estimate)
• Flash Point: 159.2°C
• Appearance: /
• Density: 2.1g/cm³
• Vapor Pressure: 2.27E-06mmHg at 25°C
• Refractive Index: 1.4738 (estimate)
• PKA: -0.14±0.50(Predicted)
• CAS DataBase Reference: NITRANILIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: NITRANILIC ACID(479-22-1)
• EPA Substance Registry System: NITRANILIC ACID(479-22-1)

Safety Data

• Hazardous Substances Data: 479-22-1(Hazardous Substances Data)

Usage

Chemical Properties

Flat, yellow crystals.Loses H2O at 100C, decomposes explosively at 170C. Soluble in water and alcohol; insoluble in ether.

Hazard

Fire risk when heated. Evolves toxic fumes on decomposition.

InChI:InChI=1/C6H2N2O8/c9-3-1(7(13)14)4(10)6(12)2(5(3)11)8(15)16/h9,12H

Upstream product

• 118-75-2 chloranil 
• 123-31-9 hydroquinone 
• 106-51-4 p-benzoquinone 
• 610-92-4 2,5-dihydroxy-1,4-benzenedicarboxylic acid 
• 613-03-6 1,2,4-triacetoxybenzene 
• 3117-03-1 2,5-dimethoxyquinone 
• 13985-45-0 2,6-dinitrohydroquinone 
• 1205-91-0 benzene-1,4-diyl diacetate 

Downstream Products

• 98135-14-9 3,6-diamino-benzene-1,2,4,5-tetraol 
• 74-90-8 hydrogen cyanide 
• 144-62-7 oxalic acid 

Relevant articles and documents

Structures of Charge-Perturbed Molecules, 47. Disodium and Dipotassium Nitranilates: The Cyanine Distortion of the Six-Membered Carbon Ring

Crystals of lemon yellow dipotassium nitranilate and of yellow disodium nitranilate dihydrate have been grown and their structures determined at 290 and 200 K.The six-membered.O2N-disubstituted rings show a pronounced cyanine distortion with all four CO bonds identical and the two (OCC(NO2)CO)(1-) chains connected by single CC bonds of each 156 pm length.In the anhydrous K(1+) salt, the ring is planar, but in the Na(1+) hydrate salt it exhibits a twist conformation.Quantum chemical calculations allow to reproduce the structure in every detail, demonstrate strong charge alternation along the cyanine with considerable delocalozation into the O2N acceptor substituents, and suggest that the rather long connecting CC bonds contain positively charged carbon centers on both ends.In addition, metal ion coordination effects as well as the rather high pKa value of nitranilic acid are rationalized. - Keywords: Cyanine Distortion of C6-Rings, Single Crystal Structures, Semiempirical Calculations