Dinitrobenzene

Dinitrobenzenes are nitrobenzenes composed of a benzene ring and two nitro group (-NO₂) substituents. The three possible arrangements of the nitro groups afford three isomers, 1,2-dinitrobenzene, 1,3-dinitrobenzene, and 1,4-dinitrobenzene. Each isomer has the chemical formula C₆H₄N₂O₄ and a molar mass of about 168.11 g/mol. 1,3-Dinitrobenzene is the most common isomer and it is used in the manufacture of explosives.

Properties

The dinitrobenzenes are all crystalline solids. The boiling points of the three isomers are relatively close; however, the melting points significantly differ. 1,4-Dinitrobenzene, which has the highest symmetry, has the highest melting point.

class="wikitable sortable float-right" style="text-align:center; font-size:90%"

colspan="4" style="background:#f8eaba" | Dinitrobenzenes

align="left" | IUPAC name

| 1,2-Dinitrobenzene

1,3-Dinitrobenzene

1,4-Dinitrobenzene

class="hintergrundfarbe1" align="left" | Other names

| o-Dinitrobenzene

m-Dinitrobenzene

p-Dinitrobenzene

align="left" | Chemical structure

| 90px

| 45px

rowspan="2" align="left" | CAS number

| 528-29-0

99-65-0

100-25-4

colspan="3" | 25154-54-5 (Unspecified isomers){{GESTIS|ZVG=530034|CAS=25154-54-5}}

align="left" | PubChem

| {{PubChem|10707}}

align="left" | Chemical formula

| colspan="3" | C₆H₄N₂O₄

align="left" | Molar mass

| colspan="3" | 168.11 g/mol

Magnetic Susceptibility

| -65.98·10⁻⁶ cm³/mol

| -70.53·10⁻⁶ cm³/mol

| -68.30·10⁻⁶ cm³/mol

align="left" | Physical state

| colspan="3" | solid

align="left" | Appearance

| white solid

yellowish solid

pale yellow solid{{cite journal|author=E. B. Starkey |title=P-DINITROBENZENE |journal=Organic Syntheses |year=1939 |volume=19 |page=40 |doi=10.15227/orgsyn.019.0040}}

align="left" | Melting point

| 118 °C{{GESTIS|ZVG=19920|CAS=528-29-0|Date=11 March 2008}}

| 89.6 °C{{GESTIS|ZVG=16330|CAS=99-65-0|Date=11 March 2008}}

| 174 °C{{GESTIS|ZVG=38820|CAS=100-25-4|Date=11 March 2008}}

align="left" | Boiling point

| 318 °C

| 297 °C

| 299 °CBrockhaus ABC Chemie, VEB F.A. Brockhaus Verlag, Leipzig 1971.

align="left" | Density

| 1.565 g/cm³ (17 °C)

1.575 g/cm³ (18 °C)

1.625 g/cm³ (18 °C)

rowspan="2" align="left" | Vapor pressure

| 0.08 Pa (30 °C){{cite journal | doi = 10.1016/j.tca.2010.11.034 | title=Triacetone triperoxide thermogravimetric study of vapor pressure and enthalpy of sublimation in 303–338K temperature range | journal=Thermochimica Acta | date=2011 | volume=514 | issue=1–2 | pages=37–43 | first=Hilsamar | last=Félix-Rivera}})

| 0.07 Pa (30 °C)

0.34 Pa (50 °C)

| 0.23 Pa (50 °C)

align="left" | Solubility

| colspan="3" | Insoluble in water

align="left" | GHS hazards{{GHS2021|ref|annex=3}}

| colspan="3" | 75px 75px 75px

align="left" | H phrases

| colspan="3" | {{H-phrases|300|310|330|373|410}}

align="left" | P phrases

| colspan="3" | {{P-phrases|260|262|264|270|271|273|280|284|301+310|302+350|304+340|310|314|320|321|322|330|361|363|391|403+233|405|501}}

References

Category:Nitrobenzenes