3-Nitrotoluene

3-Nitrotoluene
Names
	Preferred IUPAC name 1-Methyl-3-nitrobenzene
	Other names m-Nitrotoluene
Identifiers
CAS Number	99-08-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:39931;
ChemSpider	21106146;
ECHA InfoCard	100.002.480
PubChem CID	7422;
UNII	29A9W826KQ ;
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
Odor	mild, aromatic
Density	1.1581 g·cm−3 @ 20°C
Melting point	15.5 °C (59.9 °F; 288.6 K)
Boiling point	232 °C (450 °F; 505 K)
Solubility in water	0.05% (20°C)
Vapor pressure	0.1 mmHg (20°C)
Magnetic susceptibility (χ)	-72.71·10−6 cm3/mol
Hazards
Flash point	106 °C; 223 °F; 379 K
Explosive limits	1.6%-?
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 5 ppm (30 mg/m3) [skin]
REL (Recommended)	TWA 2 ppm (11 mg/m3) [skin]
IDLH (Immediate danger)	200 ppm
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

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]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ NIOSH Pocket Guide to Chemical Hazards. "#0463". 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.
^ ^a ^b Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
^ Amé Pictet; Eug. Khotinsky (January 1907). "Über Acetylnitrat". Berichte der Deutschen Chemischen Gesellschaft (in German). 40 (1): 1163–1166. doi:10.1002/CBER.190704001172. ISSN 0365-9496. Wikidata Q61714426.

External links

CDC - NIOSH Pocket Guide to Chemical Hazards - m-Nitrotoluene

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[PGCH-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ NIOSH Pocket Guide to Chemical Hazards. "#0463". National Institute for Occupational Safety and Health (NIOSH).

[CRC_85-2] 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.

[Booth-3] Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.

[4] Amé Pictet; Eug. Khotinsky (January 1907). "Über Acetylnitrat". Berichte der Deutschen Chemischen Gesellschaft (in German). 40 (1): 1163–1166. doi:10.1002/CBER.190704001172. ISSN 0365-9496. Wikidata Q61714426.

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