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2-Nitrotoluene

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]

2-Nitrotoluene
Names
Preferred IUPAC name
1-Methyl-2-nitrobenzene
Other names
o-Nitrotoluene, o-Methylnitrobenzene, 2-Methylnitrobenzene, ortho-Nitrotoluene
Identifiers
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:33098 Y
ChEMBL
  • ChEMBL47047 Y
ChemSpider
  • 21106144 Y
ECHA InfoCard 100.001.685
EC Number
  • 201-853-3
KEGG
  • C19597
  • 6944
RTECS number
  • XT3150000
UNII
  • 6Q9N88YIAY
UN number 1664
  • DTXSID4025791
  • InChI=1S/C7H7NO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3 Y
    Key: PLAZTCDQAHEYBI-UHFFFAOYSA-N 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
  • Cc1ccccc1[N+](=O)[O-]
Properties
C7H7NO2
Molar mass 137.138 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]
0.07% (20°C)[1]
Vapor pressure 0.1 mmHg (20°C)[1]
-72.28·10−6 cm3/mol
Hazards
GHS labelling:
Danger
H302, H340, H350, H361, H411
P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, P501
NFPA 704 (fire diamond)
Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
Flash point 106 °C; 223 °F; 379 K[1]
Explosive limits 2.2%-?[1]
Lethal dose or concentration (LD, LC):
891 mg/kg (oral, rat)
970 mg/kg (oral, mouse)
1750 mg/kg (oral, rabbit)[3]
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).
N verify (what is YN ?)

Synthesis and reactions edit

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 edit

  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).
  2. ^ 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.
  3. ^ "Nitrotoluene (o-, m-, p-isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ 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 edit

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

nitrotoluene, ortho, nitrotoluene, organic, compound, with, formula, ch3c6h4no2, pale, yellow, liquid, that, crystallizes, forms, called, mainly, precursor, toluidine, which, intermediate, production, various, dyes, names, preferred, iupac, name, methyl, nitro. 2 Nitrotoluene or ortho nitrotoluene is an organic compound with the formula CH3C6H4NO2 It is pale yellow liquid that crystallizes in two forms called a 9 27 C and b 3 17 C It is mainly a precursor to o toluidine which is an intermediate in the production of various dyes 4 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 Y PubChem 3D model JSmol Interactive image ChEBI CHEBI 33098 Y ChEMBL ChEMBL47047 Y ChemSpider 21106144 Y 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 YKey PLAZTCDQAHEYBI UHFFFAOYSA N NInChI 1S C7H7NO2 c1 6 4 2 3 5 7 6 8 9 10 h2 5H 1H3Key PLAZTCDQAHEYBI UHFFFAOYSA NInChI 1S C7H7NO2 c1 6 4 2 3 5 7 6 8 9 10 h2 5H 1H3 SMILES Cc1ccccc1 N O O Properties Chemical formula C 7H 7N O 2 Molar mass 137 138 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 x 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 311 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 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 N verify what is Y N Infobox referencesSynthesis and reactions editIt 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 edit 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 editCDC NIOSH Pocket Guide to Chemical Hazards o Nitrotoluene nbsp This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 2 Nitrotoluene amp oldid 1194458271, wikipedia, wiki, book, books, library,

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