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Dinitroaniline

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Dinitroanilines are a class of chemical compounds with the chemical formula C6H5N3O4. They are derived from both aniline and dinitrobenzenes. There are six isomers: 2,3-dinitroaniline, 2,4-dinitroaniline, 2,5-dinitroaniline, 2,6-dinitroaniline, 3,4-dinitroaniline, and 3,5-dinitroaniline.

Dinitroanilines are intermediates in the preparation of various industrially important chemicals including dyes and pesticides. Herbicides which are derivatives of dinitroanilines include benfluralin, butralin, chlornidine, dinitramine, dipropalin, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin, and trifluralin.

2,4-Dinitroaniline can be prepared by reaction of 1-chloro-2,4-dinitrobenzene with ammonia or by acid hydrolysis of 2,4-dinitroacetanilide.[1]

Dinitroanilines are explosive and flammable with heat or friction.

Dinitroanilines
Chemical name 2,3-Dinitroaniline 2,4-Dinitroaniline 2,5-Dinitroaniline 2,6-Dinitroaniline 3,4-Dinitroaniline 3,5-Dinitroaniline
Alternate name 2,3-Dinitro-1-aminobenzene
2,3-Dinitrophenylamine
2,3-Dinitraniline
2,4-Dinitro-1-aminobenzene
2,4-Dinitrophenylamine
2,4-Dinitraniline
2,5-Dinitro-1-aminobenzene
2,5-Dinitrophenylamine
2,5-Dinitraniline
2,6-Dinitro-1-aminobenzene
2,6-Dinitrophenylamine
2,6-Dinitraniline
3,4-Dinitro-1-aminobenzene
3,4-Dinitrophenylamine
3,4-Dinitraniline
3,5-Dinitro-1-aminobenzene
3,5-Dinitrophenylamine
3,5-Dinitraniline
Chemical structure
CAS Number 602-03-9 97-02-9 619-18-1 606-22-4 610-41-3 618-87-1
26471-56-7 (isomeric mixture)
PubChem CID 136400 from PubChem CID 7321 from PubChem CID 123081 from PubChem CID 69070 from PubChem CID 136407 from PubChem CID 12068 from PubChem
Chemical formula C6H5N3O4
Molar Mass 183.12 g/mol
Appearance colorless to yellowish combustible powder
Melting point 187.8 °C[2] 136 °C (decomp.)[3] 154–158 °C 160–162 °C[4]
Density 1.646 g/cm (50 °C)[5] 1.61 g/cm[2] 1.736 g/cm 1.601 g/cm (50 °C)[5]
Solubility soluble in water (1–2 g/L at 20 °C)
GHS hazard pictograms
GHS hazard pictograms[6]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

GHS hazard pictograms[6]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

GHS hazard pictograms[6]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

GHS hazard pictograms[6]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

GHS hazard pictograms[6]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

GHS hazard pictograms[6]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

GHS hazard pictograms[6]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

GHS hazard pictograms[6]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

GHS hazard pictograms[6]
Pictogram Code Symbol description Image link
GHS01: Explosive GHS01 {{GHS exploding bomb}} Image:GHS-pictogram-explos.svg Explosive
GHS02: Flammable GHS02 {{GHS flame}} Image:GHS-pictogram-flamme.svg
GHS03: Oxidizing GHS03 {{GHS flame over circle}} Image:GHS-pictogram-rondflam.svg
GHS04: Compressed Gas GHS04 {{GHS gas cylinder}} Image:GHS-pictogram-bottle.svg
GHS05: Corrosive GHS05 {{GHS corrosion}} Image:GHS-pictogram-acid.svg Corrosive
GHS06: Toxic GHS06 {{GHS skull and crossbones}} Image:GHS-pictogram-skull.svg Accute Toxic
GHS07: Exclamation mark GHS07 {{GHS exclamation mark}} Image:GHS-pictogram-exclam.svg Irritant
GHS08: Health hazard GHS08 {{GHS health hazard}} Image:GHS-pictogram-silhouette.svg Health Hazard
GHS09: Environmental hazard GHS09 {{GHS environment}} Image:GHS-pictogram-pollu.svg Environment

See also

H- and P-phrases H300, H310, H330, H373, H411 H302, H311, H332, H373 H301, H311, H331, H373 H301, H311, H331, H373
P260, P264, P273, P280, P284, P301+P310 P260, P301+P310, P320, P361, P405, P501 P261, P280, P301+P310, P311 P261, P280, P301+P310, P311
R-phrases Template:R26/27/28 Template:R33 Template:R51/53 Template:R26/27/28 Template:R33 Template:R51/53 Template:R23/24/25 Template:R33 Template:R23/24/25 Template:R33
S-phrases Template:S1/2 Template:S28 Template:S36/37 Template:S45 Template:S61 Template:S28 Template:S36/37 Template:S45 Template:S61 Template:S28 Template:S37 Template:S45 Template:S28 Template:S37 Template:S45

References

  1. ^ WO 1991001292  Method for the Preparation of Nitroanilines
  2. ^ a b c Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ^ a b "3,5-Dinitroaniline". Sigma-Aldrich.
  5. ^ a b C. L. Yaws (2008). Thermophysical properties of chemicals and hydrocarbons (1st ed.). New York: William Andrew Inc. p. 221. ISBN 0-815-51596-0.
  6. ^ a b c d e f g h i "Globally Harmonized System of Classification and Labelling of Chemicals" (pdf). 2021. Annex 3: Codification of Statements and Pictograms (pp 268–385).