3-Nitrotoluene

{{Chembox

| Name = 3-Nitrotoluene

| ImageFile = M-Nitrotoluol.svg

| ImageSize = 100

| PIN = 1-Methyl-3-nitrobenzene

| OtherNames = m-Nitrotoluene

|Section1={{Chembox Identifiers

| CASNo = 99-08-1

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 29A9W826KQ

| PubChem = 7422

| ChemSpiderID = 21106146

| ChEBI = 39931

| SMILES = O=[N+]([O-])c1cccc(C)c1

| InChI =1S/C7H7NO2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3

}}

|Section2={{Chembox Properties

| C=7 | H=7 | N=1 | O=2

| Appearance = yellow liquid

| Odor = mild, aromatic

| Density = 1.1581 g·cm−3 @ 20°C

| MeltingPtC = 15.5

| MeltingPt_ref = {{Cite book | editor = Lide DR | title = CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data | year = 2004 | edition = 85 | publisher = CRC Press | location = Boca Ratan Florida | isbn = 0-8493-0485-7 | url-access = registration | url = https://archive.org/details/crchandbookofche81lide }}

| BoilingPtC = 232

| BoilingPt_ref =

| Solubility = 0.05% (20°C)

| VaporPressure = 0.1 mmHg (20°C)

| MagSus = −72.71·10−6 cm3/mol

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPtF = 223

| FlashPt_ref =

| ExploLimits = 1.6%-?

| AutoignitionPt =

| IDLH = 200 ppm{{PGCH|0463}}

| REL = TWA 2 ppm (11 mg/m3) [skin]

| PEL = TWA 5 ppm (30 mg/m3) [skin]

}}

}}

{{distinguish|TNT}}

3-Nitrotoluene or meta-nitrotoluene is an organic compound with the formula {{Chem2|CH3C6H4NO2}}. It is one of three isomers of nitrotoluene. A yellow liquid, it is used in the manufacture of meta-toluidine, which is an intermediate in the production of various dyes.

Synthesis and reactions

It is made by nitrating toluene by conventional mixed acid (acetyl nitrate doesn't produce it{{Cite Wikidata|Q61714426}}): this reaction mainly affords a 2:1 mixture of 2-nitro and 4-nitro isomers, but after removal of the 2-isomer, the 3-nitrotoluene can be purified by distillation. It is a precursor to toluidine, which is used in producing azo dyes.{{Ullmann|author=Gerald Booth|title=Nitro Compounds, Aromatic|year=2007|doi=10.1002/14356007.a17_411}}

References

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