3-Nitrotoluene

3-Nitrotoluene or meta-nitrotoluene is an organic compound with the formula 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.^[3]

3-Nitrotoluene

Names
Preferred IUPAC name 1-Methyl-3-nitrobenzene
Other names m-Nitrotoluene
Identifiers
CAS Number	99-08-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:39931
ChemSpider	21106146
ECHA InfoCard	100.002.480
PubChem CID	7422
UNII	29A9W826KQ Y
CompTox Dashboard (EPA)	DTXSID5021831
InChI InChI=1S/C7H7NO2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3
SMILES O=[N+]([O-])c1cccc(C)c1
Properties
Chemical formula	C7H7NO2
Molar mass	137.138 g·mol−1
Appearance	yellow liquid[1]
Odor	mild, aromatic[1]
Density	1.1581 g·cm−3 @ 20°C [2]
Melting point	15.5 °C (59.9 °F; 288.6 K)[2]
Boiling point	232 °C (450 °F; 505 K)[2]
Solubility in water	0.05% (20°C)[1]
Vapor pressure	0.1 mmHg (20°C)[1]
Magnetic susceptibility (χ)	−72.71·10−6 cm3/mol
Hazards
Flash point	106 °C; 223 °F; 379 K[1]
Explosive limits	1.6%-?[1]
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). Infobox references

Not to be confused with TNT.

Synthesis and reactions

It is made by nitrating toluene by conventional mixed acid (acetyl nitrate doesn't produce it^[4]): 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.^[3]