2-Nitrotoluene

2-Nitrotoluene
Names
	Preferred IUPAC name 1-Methyl-2-nitrobenzene
	Other names o-Nitrotoluene, o-Methylnitrobenzene, 2-Methylnitrobenzene, ortho-Nitrotoluene
Identifiers
CAS Number	88-72-2 [PubChem];
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:33098 ;
ChEMBL	ChEMBL47047 ;
ChemSpider	21106144 ;
ECHA InfoCard	100.001.685
EC Number	201-853-3;
KEGG	C19597;
PubChem CID	6944;
RTECS number	XT3150000;
UNII	6Q9N88YIAY;
UN number	1664
CompTox Dashboard (EPA)	DTXSID4025791;
	InChI InChI=1S/C7H7NO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3 Key: PLAZTCDQAHEYBI-UHFFFAOYSA-N ; InChI=1S/C7H7NO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3 Key: PLAZTCDQAHEYBI-UHFFFAOYSA-N; InChI=1S/C7H7NO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3;
	SMILES Cc1ccccc1[N+](=O)[O-];
Properties
Chemical formula	C7H7NO2
Molar mass	137.138 g·mol−1
Appearance	yellow liquid
Odor	weak, aromatic
Density	1.1611 g·cm−3 @ 19°C
Melting point	−10.4 °C (13.3 °F; 262.8 K)
Boiling point	222 °C (432 °F; 495 K)
Solubility in water	0.07% (20°C)
Vapor pressure	0.1 mmHg (20°C)
Magnetic susceptibility (χ)	-72.28·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H340, H350, H361, H411
Precautionary statements	P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, P501
NFPA 704 (fire diamond)	3 1 1
Flash point	106 °C; 223 °F; 379 K
Explosive limits	2.2%-?
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	891 mg/kg (oral, rat); 970 mg/kg (oral, mouse); 1750 mg/kg (oral, rabbit)
	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). verify (what is ?) Infobox references

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.^[4]

Synthesis and reactions

It is made by nitrating toluene at above -10 °C. This reaction affords a 2:1 mixture of 2-nitro and 4-nitro isomers.^[4]

Chlorination of 2-nitrotoluene gives two isomers of the chloronitrotoluenes. Similarly nitration gives two isomers of dinitrotoluene.

2-Nitrotoluene is mainly consumed in the production of o-toluidine, a precursor to dyes.^[4]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ NIOSH Pocket Guide to Chemical Hazards. "#0462". 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 (o-, m-, p-isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.

External links

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

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[PGCH-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ NIOSH Pocket Guide to Chemical Hazards. "#0462". 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.

[3] "Nitrotoluene (o-, m-, p-isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Booth-4] Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.

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