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Revision as of 09:25, 31 January 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_t		Latest revision as of 02:58, 9 January 2024 edit Michael7604 (talk | contribs)Extended confirmed users8,895 editsNo edit summary
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	{{Chembox		{{Chembox
			| Verifiedfields = changed
	| verifiedrevid = 411132746
			| verifiedrevid = 411133631
	| Name = 2-Nitrotoluene
			| Name = 2-Nitrotoluene
	| ImageFile = O-Nitrotoluol.svg
			| ImageFileL1 = O-Nitrotoluol.svg
	| ImageSize = 100
			| ImageSizeL1 = 100
	| IUPACName = 1-methyl-2-nitro-benzene
	| OtherNames = ''o''-Nitrotoluene		| ImageFileR1 = 2-Nitrotoluene-3D-balls.png
			| ImageSizeR1 = 100
	| Section1 = {{Chembox Identifiers
			| PIN = 1-Methyl-2-nitrobenzene
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| OtherNames = ''o''-Nitrotoluene, ''o''-Methylnitrobenzene, 2-Methylnitrobenzene, ''ortho''-Nitrotoluene
			|Section1={{Chembox Identifiers
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 47047		| ChEMBL = 47047
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 13:		Line 16:
	| InChIKey = PLAZTCDQAHEYBI-UHFFFAOYSA-N		| InChIKey = PLAZTCDQAHEYBI-UHFFFAOYSA-N
	| InChI = 1S/C7H7NO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3		| InChI = 1S/C7H7NO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3
			| CASNo_Ref = {{cascite|correct|PubChem}}
	| CASNo =
	| PubChem =		| CASNo = 88-72-2
			| PubChem = 6944
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 21106144		| ChemSpiderID = 21106144
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| SMILES = Cc1ccccc1(=O)
			| ChEBI = 33098
	| StdInChI1 =1S/C7H7NO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3
			| EC_number = 201-853-3
			| DTXSID = DTXSID4025791
			| KEGG = C19597
			| RTECS = XT3150000
			| UNNumber = 1664
			| UNII = 6Q9N88YIAY
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = PLAZTCDQAHEYBI-UHFFFAOYSA-N
			| SMILES = Cc1ccccc1(=O)
			| InChI3 =1S/C7H7NO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=7 | H=7 | N=1 | O=2
	| Formula = C<sub>7</sub>H<sub>7</sub>NO<sub>2</sub>
			| Appearance = yellow liquid<ref name=PGCH/>
	| MolarMass = 137.136
			| Odor = weak, aromatic<ref name=PGCH/>
	| Appearance =
			| Density = 1.1611 g·cm<sup>−3</sup> @ 19°C <ref name="CRC_85"/>
	| Density =
	| MeltingPt = -9.3&deg;C		| MeltingPtC = -10.4
			| MeltingPt_ref = <ref name="CRC_85">{{Cite book | editor = Lide DR | title = CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data | year = 2004 | edition = 85 | publisher = CRC Press | location = Boca Ratan Florida | isbn = 0-8493-0485-7 | url-access = registration | url = https://archive.org/details/crchandbookofche81lide }}</ref>
	| BoilingPt =
	| Solubility =		| BoilingPtC = 222
			| BoilingPt_ref = <ref name="CRC_85"/>
	}}
			| Solubility = 0.07% (20°C)<ref name=PGCH/>
	| Section3 = {{Chembox Hazards
			| VaporPressure = 0.1 mmHg (20°C)<ref name=PGCH/>
	| MainHazards =
			| MagSus = -72.28·10<sup>−6</sup> cm<sup>3</sup>/mol
	| FlashPt =
	| Autoignition =
	}}		}}
			|Section3={{Chembox Hazards
			| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|302|340|350|361|411}}
			| PPhrases = {{P-phrases|201|202|264|270|273|281|301+312|308+313|330|391|405|501}}
			| MainHazards =
			| FlashPtF = 223
			| FlashPt_ref = <ref name=PGCH/>
			| AutoignitionPt =
			| IDLH = 200 ppm<ref name=PGCH>{{PGCH|0462}}</ref>
			| LD50 = 891 mg/kg (oral, rat)<br/>970 mg/kg (oral, mouse)<br/>1750 mg/kg (oral, rabbit)<ref>{{IDLH|88722|Nitrotoluene (o-, m-, p-isomers)}}</ref>
			| REL = TWA 2 ppm (11 mg/m<sup>3</sup>) <ref name=PGCH/>
			| PEL = TWA 5 ppm (30 mg/m<sup>3</sup>) <ref name=PGCH/>
			| ExploLimits = 2.2%-?<ref name=PGCH/>
			| NFPA-F = 1
			| NFPA-H = 3
			| NFPA-R = 1
			}}
	}}		}}
			'''2-Nitrotoluene''' or '''''ortho''-nitrotoluene''' is an ] with the formula CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>NO<sub>2</sub>. 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.<ref name=Booth/>
	{{Chembox
	| Name = 3-Nitrotoluene
	| ImageFile = M-Nitrotoluol.svg
	| ImageSize = 100
	| IUPACName = 1-methyl-3-nitro-benzene
	| OtherNames = ''m''-Nitrotoluene
	| Section1 = {{Chembox Identifiers
	| CASNo =
	| PubChem =
	| ChemSpiderID = 21106146
	| SMILES = O=()c1cccc(C)c1
	| InChI = InChI=1S/C7H7NO2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3
	}}
	| Section2 = {{Chembox Properties
	| Formula = C<sub>7</sub>H<sub>7</sub>NO<sub>2</sub>
	| MolarMass = 137.136
	| Appearance =
	| Density =
	| MeltingPt = 16.1&deg;C
	| BoilingPt =
	| Solubility =
	}}
	| Section3 = {{Chembox Hazards
	| MainHazards =
	| FlashPt =
	| Autoignition =
	}}
	}}
	{{Chembox
	| Name = 4-Nitrotoluene
	| ImageFile = P-Nitrotoluol.svg
	| ImageSize = 50
	| IUPACName = 1-methyl-4-nitrobenzene
	| OtherNames = ''p''-Nitrotoluene
	| Section1 = {{Chembox Identifiers
	| CASNo =
	| PubChem =
	| ChemSpiderID = 13863774
	| SMILES = O=()c1ccc(C)cc1
	| InChI = InChI=1S/C7H7NO2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3
	}}
	| Section2 = {{Chembox Properties
	| Formula = C<sub>7</sub>H<sub>7</sub>NO<sub>2</sub>
	| MolarMass = 137.136
	| Appearance =
	| Density =
	| MeltingPt = 51.7&deg;C
	| BoilingPt =
	| Solubility =
	}}
	| Section3 = {{Chembox Hazards
	| MainHazards =
	| FlashPt =
	| Autoignition =
	}}
	}}
	'''Mononitrotoluene''', or '''methylnitrobenzene''' or '''nitrotoluene''' ('''MNT''' or '''NT'''), is a group of 3 ]s, a ] derivative of ] (or alternatively a methyl derivative of ]). Its ] is C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)(NO<sub>2</sub>).
	Mononitrotoluene comes in three ]s, differing by the relative position of the ] and ] groups:
	* '''''ortho''-nitrotoluene''' ('''ONT'''), '''''o''-nitrotoluene''', or '''2-nitrotoluene''', ] {{CASREF|CAS=88-72-2}}. It is a pale yellow liquid with a subtle, characteristic smell. It is non-] and noncorrosive.
	* '''''meta''-nitrotoluene''' ('''MNT'''), '''''m''-nitrotoluene''', or '''3-nitrotoluene''', CAS number {{CASREF|CAS=99-08-1}}. It is a yellowish-greenish to yellow liquid with weak fragrance.
			==Synthesis and reactions==
	* '''''para''-nitrotoluene''' ('''PNT'''), '''''p''-nitrotoluene''', or '''4-nitrotoluene''', CAS number {{CASREF|CAS=99-99-0}}. It is a pale yellow material forming ] crystals and has a somewhat pleasant, characteristic smell. It is almost insoluble in water.
			It is made by ] ] at above -10&nbsp;°C. This reaction affords a 2:1 mixture of 2-nitro and 4-nitro isomers.<ref name=Booth/>
			Chlorination of 2-nitrotoluene gives two isomers of the chloronitrotoluenes. Similarly nitration gives two isomers of dinitrotoluene.
	Typical use of nitrotoluene is in production of ]s, ]s, agricultural chemicals, and photographic chemicals.
			2-Nitrotoluene is mainly consumed in the production of ], a precursor to dyes.<ref name=Booth>{{Ullmann|author=Gerald Booth|title=Nitro Compounds, Aromatic|year=2007|doi=10.1002/14356007.a17_411}}</ref>
	''ortho''-Mononitrotoluene and ''para''-mononitrotoluene can be also used as ]s for ].
	==See also==		== References ==
			{{reflist}}
	*]
	*]
	*]
	*]
			==External links==
	]
			*
	]
	]
			{{DEFAULTSORT:Nitrotoluene, 2-}}
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			]
	{{Organic-compound-stub}}
			]
			{{aromatic-stub}}
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	]
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