4-Nitrotoluene
Chemical compound
From Wikipedia, the free encyclopedia
4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.
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| Names | |
|---|---|
| Preferred IUPAC name
1-Methyl-4-nitrobenzene | |
| Other names
p-nitrotoluene p-mononitrotoluene p-methylnitrobenzene | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.002.553 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C7H7NO2 | |
| Molar mass | 137.138 g·mol−1 |
| Appearance | crystalline solid[1] |
| Odor | weak, aromatic[1] |
| Density | 1.1038 g·cm−3 (75 °C) [2] |
| Melting point | 51.63 °C (124.93 °F; 324.78 K)[2] |
| Boiling point | 238.3 °C (460.9 °F; 511.4 K)[2] |
| 0.04% (20°C)[1] | |
| Vapor pressure | 0.1 mmHg (20°C)[1] |
| −72.06·10−6 cm3/mol | |
| Hazards[3] | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
moderately toxic |
| GHS labelling: | |
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| Danger | |
| H301, H311, H331, H373, H411 | |
| P260, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, P501 | |
| Flash point | 106 °C; 223 °F; 379 K[1] |
| Explosive limits | 1.6%–?[1] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
1231 mg/kg (mouse, oral) 1330 mg/kg (rat, oral) 1450 mg/kg (rabbit, oral)[4] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) |
TWA 5 ppm (30 mg/m3) [skin][1] |
REL (Recommended) |
TWA 2 ppm (11 mg/m3) [skin][1] |
IDLH (Immediate danger) |
200 ppm[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions
Together with other isomers, 4-nitrotoluene is prepared by nitration of toluene,[5] commonly using titanium(IV) nitrate.[6] It undergoes the reactions typical for nitrobenzene derivatives, e.g. hydrogenation gives p-toluidine.
Oxidation of the methyl substituent of 4-nitrotoluene has been extensively investigated. Depending on the conditions, oxidation yields 4-nitrobenzaldehyde diacetate,[7] 4-nitrobenzenoic acid,[8] and 4,4'-dinitrobibenzyl.[9] Treatment of 4-nitrotoluene with bromine gives the 4-nitrobenzyl bromide.[10]
Applications
The principal application involves its sulfonation to give the 4-nitrotoluene-2-sulfonic acid (with the –SO3H group adjacent to methyl). This species can be oxidatively coupled to produce stilbene derivatives,[11] which are used as dyes.[12] Representative derivatives include the molecular and salt forms of 4,4'-dinitroso- and the 4,4'-dinitro-2,2'-stilbenedisulfonic acids, e.g. disodium 4,4'-dinitrostilbene-2,2'-disulfonate.[13]
Safety
Evidence exists for toxicity and carcinogenicity in mice.[14]