2,4-Dinitroaniline

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2,4-Dinitroaniline[1][2]
The ball-and-stick structure of 2,4-dinitroaniline
The chemical structure of 2,4-dinitroaniline
Names
Preferred IUPAC name
2,4-Dinitroaniline
Other names
1-Amino-2,4-dinitrobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.322 Edit this at Wikidata
EC Number
  • 202-553-5
KEGG
RTECS number
  • BX9100000
UNII
UN number 1596
  • InChI=1S/C6H5N3O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H,7H2
    Key: LXQOQPGNCGEELI-UHFFFAOYSA-N
  • C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])N
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
 Toxic, Health and Environmental hazards
GHS labelling:
GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
3
1
3
Flash point 224 °C (435 °F; 497 K)
350
Lethal dose or concentration (LD, LC):
285 mg/kg (oral, rat)
Related compounds
Related compounds
 2,4,6-Trinitroaniline

4-Nitroaniline

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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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.[citation needed]

2,4-Dinitroaniline can be reduced to 1,2-diamino-4-nitrobenzene and further reduced to 1,2,4-triaminobenzene.

Uses

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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

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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

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References

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  1. ^ "2,4-Dinitroaniline CAS#: 97-02-9". www.chemicalbook.com. Archived from the original on 2019-03-23. Retrieved 2019-03-23.
  2. ^ PubChem. "2,4-Dinitroaniline". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-03-23.
  3. ^ https://www.chembk.com/en/chem/benzenamine,%202,4-dinitro-
  4. ^ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
  5. ^ https://www.sigmaaldrich.com/US/en/sds/sial/45963

https://www.sigmaaldrich.com/US/en/sds/sial/45963