2,4-Dinitroaniline is a chemical compound with a formula of C6H5N3O4. It is used as an explosive and as a reagent to detect and characterize aldehydes and ketones.
It can be also prepared by the electrophilic aromatic substitution of aniline. Direct nitration should not be used due to the reactivity of aniline. (i.e. It can be protonated to anilinium or oxidized easily.) Instead the acetyl protection should be used.
Basicityedit
Compared to aniline, the basicity of 2,4-dinitroaniline is even weaker. It is due to the electron-withdrawing nature of the nitro groups. This makes the pKa of conjugate acid of 2,4-dinitroaniline being even lower than that of hydronium ions, meaning that it is a strong acid.
The protons in the amino group is also much more acidic than that of aniline.
Usesedit
2,4-Dinitroaniline is usually used as an explosive, although the material possess a negative oxygen balance and can be improved by combining it with an oxidizer such as ammonium nitrate. When in pure form, 2,4-Dinitroaniline has a VoD of 4,800 m/s at 1.61 g/cm3 molecular density.
2,4-Dinitroaniline is moderately toxic, with a lethal dose of 285 mg/kg. However, the main danger is that it is explosive and flammable with heat or friction encouraging these properties.
note 1 Calculated from the detonation velocity of 2,4,6-trinitroaniline by multiplying 2/3
March 07, 2024
dinitroaniline, chemical, compound, with, formula, c6h5n3o4, used, explosive, reagent, detect, characterize, aldehydes, ketones, ball, stick, structure, dinitroanilinethe, chemical, structure, dinitroanilinenamespreferred, iupac, name, other, names, amino, din. 2 4 Dinitroaniline is a chemical compound with a formula of C6H5N3O4 It is used as an explosive and as a reagent to detect and characterize aldehydes and ketones 2 4 Dinitroaniline 1 2 The ball and stick structure of 2 4 dinitroanilineThe chemical structure of 2 4 dinitroanilineNamesPreferred IUPAC name 2 4 DinitroanilineOther names 1 Amino 2 4 dinitrobenzeneIdentifiersCAS Number 97 02 93D model JSmol Interactive imageChEBI CHEBI 34242ChEMBL ChEMBL354318ChemSpider 7045ECHA InfoCard 100 002 322EC Number 202 553 5KEGG C14713PubChem CID 7321RTECS number BX9100000UNII 5BI780R6W6UN number 1596CompTox Dashboard EPA DTXSID1021823InChI InChI 1S C6H5N3O4 c7 5 2 1 4 8 10 11 3 6 5 9 12 13 h1 3H 7H2Key LXQOQPGNCGEELI UHFFFAOYSA NSMILES C1 CC C C C1 N O O N O O NPropertiesChemical formula C 6H 5N 3O 4Molar mass 183 123 g mol 1Appearance Colorless to yellowish combustible powderDensity 1 61 g cm3Melting point 187 8 C 370 0 F 460 9 K Boiling point DecomposesSolubility in water 0 06 g L 20 C Solubility Soluble in acetone ethyl acetate acetonitrile and most alcohols insoluble in waterAcidity pKa 4 53 conjugate acid 18 46Explosive dataShock sensitivity LowFriction sensitivity LowDetonation velocity 4 800 m s note 1 HazardsOccupational safety and health OHS OSH Main hazards Explosive Flammable Toxic Health and Environmental hazardsGHS labelling PictogramsSignal word DangerHazard statements H228 H300 H310 H330 H373 H411Precautionary statements P260 P262 P264 P270 P271 P273 P280 P284 P301 P310 P302 P350 P304 P340 P310 P314 P320 P321 P322 P330 P361 P363 P391 P403 P233 P405 P501NFPA 704 fire diamond 313Flash point 224 C 435 F 497 K Lethal dose or concentration LD LC LD50 median dose 285 mg kg oral rat Related compoundsRelated compounds 2 4 6 Trinitroaniline 4 NitroanilineExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Preparation 2 Basicity 3 Uses 4 Safety 5 See also 6 ReferencesPreparation edit2 4 Dinitroaniline can be prepared by reaction of 1 chloro 2 4 dinitrobenzene with ammonia It can be also prepared by the electrophilic aromatic substitution of aniline Direct nitration should not be used due to the reactivity of aniline i e It can be protonated to anilinium or oxidized easily Instead the acetyl protection should be used Basicity editCompared to aniline the basicity of 2 4 dinitroaniline is even weaker It is due to the electron withdrawing nature of the nitro groups This makes the pKa of conjugate acid of 2 4 dinitroaniline being even lower than that of hydronium ions meaning that it is a strong acid C 6 H 3 NH 3 NO 2 2 H 2 O C 6 H 3 NH 2 NO 2 2 H 3 O displaystyle ce C6H3 NH3 NO2 2 H2O gt C6H3 NH2 NO2 2 H3O nbsp The protons in the amino group is also much more acidic than that of aniline Uses edit2 4 Dinitroaniline is usually used as an explosive although the material possess a negative oxygen balance and can be improved by combining it with an oxidizer such as ammonium nitrate When in pure form 2 4 Dinitroaniline has a VoD of 4 800 m s at 1 61 g cm3 molecular density It is also used for the manufacture of certain azo dyes and disperse dyes as well as in printing ink toner and the preparation of preservatives The compound also finds applications as an intermediate in the synthesis of neutral dyes sulfur dyes and organic pigments Safety edit2 4 Dinitroaniline is moderately toxic with a lethal dose of 285 mg kg However the main danger is that it is explosive and flammable with heat or friction encouraging these properties See also edit2 4 6 Trinitroaniline 4 NitroanilineReferences edit 2 4 Dinitroaniline CAS 97 02 9 www chemicalbook com Retrieved 2019 03 23 PubChem 2 4 Dinitroaniline pubchem ncbi nlm nih gov Retrieved 2019 03 23 note 1 Calculated from the detonation velocity of 2 4 6 trinitroaniline by multiplying 2 3 Retrieved from https en wikipedia org w index php title 2 4 Dinitroaniline amp oldid 1155103292, wikipedia, wiki, book, books, library,
