4-Nitrotoluene

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4-Nitrotoluene
P-Nitrotoluol.svg
Names
Preferred IUPAC name
1-Methyl-4-nitrobenzene
Other names
p-nitrotoluene
p-mononitrotoluene, p-methylnitrobenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.553 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H7NO2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3
    Key: ZPTVNYMJQHSSEA-UHFFFAOYSA-N
  • O=[N+]([O-])c1ccc(C)cc1
Properties
C7H7NO2
Molar mass 137.138 g·mol−1
Appearancecrystalline 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
moderately toxic
Flash point 106 °C; 223 °F; 379 K [1]
Explosive limits 1.6%–? [1]
Lethal dose or concentration (LD, LC):
1231 mg/kg (mouse, oral)
1330 mg/kg (rat, oral)
1450 mg/kg (rabbit, oral) [3]
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).

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.

Contents

Synthesis and reactions

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

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

Evidence exists for toxicity and carcinogenicity in mice. [13]

Related Research Articles

<i>p</i>-Phenylenediamine Chemical compound

p-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna.

Hydroiodic acid Solution of hydrogen iodide (HI) in water

Hydroiodic acid is an aqueous solution of hydrogen iodide (HI). It is a strong acid, one that is ionized completely in an aqueous solution. It is colorless. Concentrated solutions are usually 48% to 57% HI.

In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.

Chlorobenzene Aromatic organochlorine compound

Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

There are three isomers of toluidine, which are organic compounds. These isomers are o-toluidine, m-toluidine, and p-toluidine, with the prefixed letter abbreviating, respectively, ortho; meta; and para. All three are aryl amines whose chemical structures are similar to aniline except that a methyl group is substituted onto the benzene ring. The difference between these three isomers is the position where the methyl group (–CH3) is bonded to the ring relative to the amino functional group (–NH2); see illustration of the chemical structures below.

2,4-Dinitrotoluene Organic chemical compound

2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.

Chlorotoluene is a group of three isomeric chemical compounds. They consist of a disubstituted benzene ring with one chlorine atom and one methyl group.

<i>para</i>-Cresidine Chemical compound

para-Cresidine is an organic compound with the formula CH3OC6H3(CH3)NH2. It is a white solid that is soluble in organic solvents. The compound features both amine and methoxy functional groups. It is used as an intermediate in preparation of dyes and pigments.

Durene Chemical compound

Durene, or 1,2,4,5-tetramethylbenzene, is an organic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as an alkylbenzene. It is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and isodurene (1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.

Tolidine Chemical compound

2-Tolidine (orthotolidine, o-tolidine; not to be confused with o-toluidine) is an organic compound with the chemical formula (C6H4(CH3)NH2)2. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorless compound although commercial samples are often colored. It is slightly soluble in water. It forms salts with acids, such as the hydrochloride, which is commercially available.

<i>o</i>-Anisidine Chemical compound

o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

2-Nitrobenzaldehyde Chemical compound

2-Nitrobenzaldehyde is an organic aromatic compound containing a nitro group ortho to formyl. 2-Nitrobenzaldehyde once was produced as an intermediate in the synthesis of the popular dye Indigo.

Nitrobenzoic acid Index of chemical compounds with the same name

Nitrobenzoic acids are derivatives of benzoic acid. Two are commercially important. They are about ten times more acidic than the parent benzoic acid.

4-Nitrochlorobenzene Chemical compound

4-Nitrochlorobenzene is the organic compound with the formula ClC6H4NO2. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including common antioxidants found in rubber. Other isomers with the formula ClC6H4NO2 include 2-nitrochlorobenzene and 3-nitrochlorobenzene.

Dinitro-<i>ortho</i>-cresol Chemical compound

Dinitro-ortho-cresol (DNOC) is an organic compound with the structural formula CH3C6H2(NO2)2OH. It is a yellow solid that is only slightly soluble in water. DNOC and some related derivatives have been used as herbicides.

3-Nitrotoluene or meta-nitrotoluene is a yellow liquid. It is used in the manufacture of meta-toluidine. It is an intermediate in the production of various dyes.

2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes.

2,4-Diaminotoluene Chemical compound

2,4-Diaminotoluene is an organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. It is a white solid although commercial samples are often yellow-tan.

1,4-Dichloro-2-nitrobenzene Chemical compound

1,4-Dichloro-2-nitrobenzene is an organic compound with the formula C6H3Cl2NO2. One of several isomers of dichloronitrobenzene, it is a yellow solid that is insoluble in water. It is produced by nitration of 1,4-dichlorobenzene. It is a precursor to many derivatives of commercial interest. Hydrogenation gives 1,4-dichloroaniline. Nucleophiles displace the chloride adjacent to the nitro group: ammonia gives the aniline derivative, aqueous base gives the phenol derivative, and methoxide gives the anisole derivative. These compounds are respectively 4-chloro-2-nitroaniline, 4-chloro-2-nitrophenol, and 4-chloro-2-nitroanisole.

4,4′-Diamino-2,2′-stilbenedisulfonic acid Chemical compound

4,4′-Diamino-2,2′-stilbenedisulfonic acid is the organic compound with the formula (H2NC6H3SO3H)2C2H2. It is a white, water-soluble solid. Structurally, it is a derivative of trans-stilbene, containing amino and sulfonic acid functional groups on each of the two phenyl rings.

References

  1. 1 2 3 4 5 6 7 8 9 NIOSH Pocket Guide to Chemical Hazards. "#0464". National Institute for Occupational Safety and Health (NIOSH).
  2. 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.
  3. ↑ "Nitrotoluene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.
  5. ↑ 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.
  6. ↑ Tamio Nishimura (1956). "o- and p-Nitrobenzaldiacetate". Organic Syntheses. 36: 58. doi:10.15227/orgsyn.036.0058.
  7. ↑ O. Kamm, A. O. Matthews (1922). "p-Nitrobenzoic Acid". Organic Syntheses. 2: 53. doi:10.15227/orgsyn.002.0053.
  8. ↑ Herbert O. House (1954). "p,p'-Dinitrobibenzyl". Organic Syntheses. 34: 35. doi:10.15227/orgsyn.034.0035.
  9. ↑ G. H. Coleman, G. E. Honeywell (1936). "p-Nitrobenzyl Bromide". Organic Syntheses. 16: 54. doi:10.15227/orgsyn.016.0054.
  10. ↑ 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.
  11. ↑ Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys (2005). Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245.
  12. ↑ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN   978-3527306732.
  13. ↑ 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.
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