2-Nitrotoluene

2-Nitrotoluene
Names
	IUPAC name 1-methyl-2-nitro-benzene
	Other names o-Nitrotoluene, o-Methylnitrobenzene, 2-Methylnitrobenzene, ortho-Nitrotoluene
Identifiers
CAS Number	88-72-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:33098 ;
ChEMBL	ChEMBL47047 ;
ChemSpider	21106144 ;
ECHA InfoCard	100.001.685
	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	137.14 g·mol−1
Appearance	yellow liquid[1]
Odor	weak, aromatic[1]
Density	1.1611 g·cm−3 @ 19°C [2]
Melting point	−10.4 °C (13.3 °F; 262.8 K)[2]
Boiling point	222 °C (432 °F; 495 K)[2]
Solubility in water	0.07% (20°C)[1]
Vapor pressure	0.1 mmHg (20°C)[1]
Magnetic susceptibility (χ)	-72.28·10−6 cm3/mol
Hazards
Flash point	106 °C; 223 °F; 379 K [1]
Explosive limits	2.2%-?[1]
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	891 mg/kg (oral, rat); 970 mg/kg (oral, mouse); 1750 mg/kg (oral, rabbit)[3]
	US health exposure limits (NIOSH):
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).
	verify (what is ?)
	Infobox references

2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH₃C₆H₄NO₂. It is pale yellow liquid that is a versatile 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 gives two isomers of the chloronitrotoluenes. Similarly nitration gives two isomers of dinitrotoluene.

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

References

1 2 3 4 5 6 7 8 9 "NIOSH Pocket Guide to Chemical Hazards #0462". National Institute for Occupational Safety and Health (NIOSH).
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.
↑ "Nitrotoluene (o-, m-, p-isomers)". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
1 2 3 Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.

External links

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

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[PGCH-1] 1 2 3 4 5 6 7 8 9 "NIOSH Pocket Guide to Chemical Hazards #0462". National Institute for Occupational Safety and Health (NIOSH).

[CRC_85-2] 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 (o-, m-, p-isomers)". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Booth-4] 1 2 3 Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.