4-Nitrotoluene
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| Names | |
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| 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 | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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moderately toxic |
| Flash point | 106 °C; 223 °F; 379 K[1] |
| Explosive limits | 1.6%–?[1] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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1231 mg/kg (mouse, oral) 1330 mg/kg (rat, oral) 1450 mg/kg (rabbit, oral)[3] |
| NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 5 ppm (30 mg/m3) [skin][1] |
REL (Recommended)
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TWA 2 ppm (11 mg/m3) [skin][1] |
IDLH (Immediate danger)
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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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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.
Synthesis and reactions
[edit]Together with other isomers, 4-nitrotoluene is prepared by nitration of toluene,[4] commonly using titanium(IV) nitrate.[5] 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,[6] 4-nitrobenzenoic acid,[7] and 4,4'-dinitrobibenzyl.[8] Treatment of 4-nitrotoluene with bromine gives the 4-nitrobenzyl bromide.[9]
Applications
[edit]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,[10] which are used as dyes.[11] 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.[12]
Safety
[edit]Evidence exists for toxicity and carcinogenicity in mice.[13]
References
[edit]- ^ a b c d e f g h i NIOSH Pocket Guide to Chemical Hazards. "#0464". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c 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 or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
- ^ Amos, D.W.; D.A. Baines, G.W. Flewett (1973). "Nitration by titanium (IV) nitrate". Tetrahedron Letters. 14 (34): 3191–3194. doi:10.1016/S0040-4039(00)79808-X. ISSN 0040-4039.
- ^ Tamio Nishimura (1956). "o- and p-Nitrobenzaldiacetate". Organic Syntheses. 36: 58. doi:10.15227/orgsyn.036.0058.
- ^ O. Kamm, A. O. Matthews (1922). "p-Nitrobenzoic Acid". Organic Syntheses. 2: 53. doi:10.15227/orgsyn.002.0053.
- ^ Herbert O. House (1954). "p,p'-Dinitrobibenzyl". Organic Syntheses. 34: 35. doi:10.15227/orgsyn.034.0035.
- ^ G. H. Coleman, G. E. Honeywell (1936). "p-Nitrobenzyl Bromide". Organic Syntheses. 16: 54. doi:10.15227/orgsyn.016.0054.
- ^ Cumming, William M.; Hopper, I. Vance; Wheeler, T. Sherlock (1926). "Preparation 294.—Dinitro-Stilbene-Disulphonic Acid (Na salt)". Systematic Organic Chemistry: Modern Methods of Preparation and Estimation. New York: D. Van Nostrand Company. p. 314.
- ^ Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245. ISBN 3527306730.
- ^ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
- ^ 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.