4-Nitrotoluene
 | |
| Names | |
|---|---|
| IUPAC name
1-Methyl-4-nitrobenzene | |
| Other names
p-Nitrotoluene | |
| Identifiers | |
| 99-99-0 | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 13863774 |
| ECHA InfoCard | 100.002.553 |
| PubChem | 7473 |
| |
| |
| Properties | |
| C7H7NO2 | |
| Molar mass | 137.14 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] |
| Hazards | |
| 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) 1960 mg/kg (rat, oral) 1750 mg/kg (rabbit, oral)[3] |
| US health exposure limits (NIOSH): | |
| 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). | |
| Infobox references | |
4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. This compound is mainly used to prepare dyes.
Synthesis and reactions
Together with other isomers, 4-nitrotoluene is prepared by nitration of toluene.[4] It undergoes the expected reactions, e.g. hydrogenation gives p-toluidine.
Applications
The principle application involves its sulfonation to give the 4-nitrotoluene-2-sulfonic acid (SO3H group adjacent to methyl). This species is produced on a large scale since it can be coupled to make stilbene derivatives which are used as dyes. Representative derivatives include 4,4'-dinitroso- and the 4,4'-dinitro-2,2'-stilbenedisulfonic acids.[4]
Safety
There is some evidence for toxicity and carcinogenecity in mice.[5]
References
- 1 2 3 4 5 6 7 8 9 "NIOSH Pocket Guide to Chemical Hazards #0464". National Institute for Occupational Safety and Health (NIOSH).
- 1 2 3 Lide DR, ed. (2004). CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data (85 ed.). Boca Ratan Florida: CRC Press. ISBN 0-8493-0485-7.
- ↑ "Nitrotoluene". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
- 1 2 Gerald Booth "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411
- ↑ National Toxicology, Program (2002). "Toxicology and carcinogenesis studies of p-nitrotoluene (CAS no. 99-99-0) in F344/N rats and B6C3F(1) mice (feed studies)". National Toxicology Program technical report series (498): 1–277. PMID 12118261.
External links
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