2,4-Dinitroaniline
The ball-and-stick structure of 2,4-dinitroaniline
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The chemical structure of 2,4-dinitroaniline
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| Names | |
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| Preferred IUPAC name
2,4-Dinitroaniline | |
| Other names
1-Amino-2,4-dinitrobenzene
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.322 |
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| KEGG | |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 1596 |
CompTox Dashboard (EPA)
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| Properties | |
| C6H5N3O4 | |
| Molar mass | 183.123 g·mol−1 |
| Appearance | Colorless to yellowish combustible powder |
| Density | 1.61 g/cm3 |
| Melting point | 187.8 °C (370.0 °F; 460.9 K) |
| Boiling point | Decomposes |
| 0.06 g/L (20 °C) | |
| Solubility | Soluble in acetone, ethyl acetate, acetonitrile and most alcohols · insoluble in water |
| Acidity (pKa) | -4.53 (conjugate acid) ; 18.46 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Toxic, Health and Environmental hazards |
| GHS labelling: | |
| Danger | |
| H300, H310, H330, H373, H411 | |
| P260, P262, P264, P270, P271, P273, P280, P284, P301+P310+P330, P302+P350, P304+P340+P310, P314, P362, P391, P403+P233, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 224 °C (435 °F; 497 K) |
| 350 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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285 mg/kg (oral, rat) |
| Related compounds | |
Related compounds
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2,4,6-Trinitroaniline |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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2,4-Dinitroaniline is an organic compound with a formula of (O2N)2C6H3NH2. It is used as an intermediate in the manufacturing and production of pesticides, herbicides, pharmaceuticals, and dyes.[3] Compared to aniline, the basicity of 2,4-dinitroaniline is even weaker.
Preparation and reactions
2,4-Dinitroaniline can be prepared by reaction of 1-chloro-2,4-dinitrobenzene with ammonia.[4] It can be also prepared by the nitration of aniline.
2,4-Dinitroaniline can be reduced to 1,2-diamino-4-nitrobenzene and further reduced to 1,2,4-triaminobenzene.
Uses
It is 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
2,4-Dinitroaniline is toxic, with a lethal dose of 285 mg/kg. It is also reported to penetrate through skin leading to acute dermal toxicity ratings.[5] Unlike other nitroaromatics, it is not classified as an explosive.
See also
References
- ^ "2,4-Dinitroaniline CAS#: 97-02-9". www.chemicalbook.com. Archived from the original on 2019-03-23. Retrieved 2019-03-23.
- ^ PubChem. "2,4-Dinitroaniline". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-03-23.
- ^ https://www.chembk.com/en/chem/benzenamine,%202,4-dinitro-
- ^ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
- ^ https://www.sigmaaldrich.com/US/en/sds/sial/45963