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Revision as of 17:29, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473188357 of page 2-Nitrobenzaldehyde for the Chem/Drugbox validation project (updated: '').  Latest revision as of 17:32, 17 November 2024 edit Davemck (talk | contribs)Extended confirmed users120,169 editsm Clean up duplicate template arguments using findargdups; fix ref error 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 413114560 | verifiedrevid = 477214862
⚫ | ImageFileL1 = 2-nitrobenzaldehyde.svg
| Reference=<ref></ref><ref></ref>
| ImageSizeL1 = 125
⚫ | ImageFile = 2-nitrobenzaldehyde.svg
| ImageAltL1 = Skeletal formula of 2-nitrobenzaldehyde
| ImageSize = 130px
| IUPACName = 2-Nitrobenzaldehyde | ImageFileR1 = 2-Nitrobenzaldehyde-3D-balls.png
| ImageSizeR1 = 135
⚫ | OtherNames = Nitrobenzaldehyde, ortho-nitrobenzaldehyde, ''o''-nitrobenzaldehyde
| ImageAltR1 = Ball-and-stick model of the 2-nitrobenzaldehyde molecule
⚫ | Section1 = {{Chembox Identifiers
| PIN = 2-Nitrobenzaldehyde
⚫ | PubChem = 11101
⚫ | OtherNames = Nitrobenzaldehyde<br />''ortho''-Nitrobenzaldehyde<br />''o''-Nitrobenzaldehyde
⚫ | InChI = 1/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H
⚫ |Section1={{Chembox Identifiers
⚫ | SMILES = O=()c1ccccc1C=O
⚫ | CASNo = 552-89-6
⚫ | InChIKey = CMWKITSNTDAEDT-UHFFFAOYAD
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| ChEBI = 66927
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 166559 | ChEMBL = 166559
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 10630
| EC_number = 209-025-3
⚫ | PubChem = 11101
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 48B18Q9B8E
⚫ | InChI = 1/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H
⚫ | InChIKey = CMWKITSNTDAEDT-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H | StdInChI = 1S/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CMWKITSNTDAEDT-UHFFFAOYSA-N | StdInChIKey = CMWKITSNTDAEDT-UHFFFAOYSA-N
⚫ | SMILES = O=()c1ccccc1C=O
⚫ | CASNo = 552-89-6
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 10630
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>7</sub>H<sub>5</sub>NO<sub>3</sub> | Formula = C<sub>7</sub>H<sub>5</sub>NO<sub>3</sub>
| MolarMass = 151.12 g/mol | MolarMass = 151.12 g/mol
| Appearance = Pale yellow crystalline powder | Appearance = Pale yellow crystalline powder
| Density = | Density =
| MeltingPtC = 43 | MeltingPtC = 43
| BoilingPtC = 152 | BoilingPtC = 152
| Solubility = Insoluble | Solubility = Insoluble
| MagSus = -68.23·10<sup>−6</sup> cm<sup>3</sup>/mol
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| MainHazards = Harmful, Potentially mutagenic | MainHazards = Harmful, Potentially mutagenic
| GHS_ref=<ref>{{cite web |title=2-Nitrobenzaldehyde |url=https://pubchem.ncbi.nlm.nih.gov/compound/11101#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| RPhrases = {{R36}} {{R37}} {{R38}} {{R41}}
| SPhrases = {{S26}} {{S28}} | GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
⚫ | NFPA-H = 2
| HPhrases = {{H-phrases|302|315|319|335|412}}
⚫ | NFPA-F = 1
| PPhrases = {{P-phrases|261|264|270|271|273|280|301+312|302+352|304+340|305+351+338|312|330|332+313|337+313|362|403+233|405|501}}
⚫ | NFPA-R = 0
| NFPA-O = | NFPA-H = 2
⚫ | NFPA-F = 1
⚫ | NFPA-R = 0
⚫ | NFPA-S =
}} }}
}} }}
'''2-Nitrobenzaldehyde''' is an ] with the formula {{chem2|O2NC6H4CHO}}. It is one of three isomers of ]. It contains a ] ] adjacent to the ].<ref>{{cite book |doi=10.1002/14356007.a03_463.pub2 |chapter=Benzaldehyde |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2011 |last1=Brühne |first1=Friedrich |last2=Wright |first2=Elaine |isbn=978-3-527-30385-4 }}</ref>

==Synthesis==
The ] of ] produces mostly ]. Partly for this reason, 2-nitrobenzaldehyde is prepared by indirect routes.<ref>{{cite book |doi=10.1002/14356007.a03_463.pub2 |chapter=Benzaldehyde |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2011 |last1=Brühne |first1=Friedrich |last2=Wright |first2=Elaine |isbn=978-3-527-30385-4 }}</ref> The main routes to nitrobenzaldehyde begin with the nitration of ] or ] followed by the conversions of the resulting 2-nitrostyrene and 2-nitrocinnamic acids, respectively. ] can also be ] in high-yield to ].<ref>{{cite journal|journal=Org. Synth.|year=1953|volume=33|page=60|doi=10.15227/orgsyn.033.0060|title=o-Nitrocinnamaldehyde|author=Robert E. Buckles, M. Peter Bellis}}</ref> This compound is then oxidized to 2-nitrocinnamic acid, which is ] to the 2-nitrostyrene. The ] group can be oxidized in a number of different ways to yield 2-nitrobenzaldehyde.<ref>{{Cite journal |last1=Feng |first1=Bo |last2=Hou |first2=Zhenshan |last3=Wang |first3=Xiangrui |last4=Hu |first4=Yu |last5=Li |first5=Huan |last6=Qiao |first6=Yunxiang |date=2009-09-01 |title=Selective aerobic oxidation of styrene to benzaldehyde catalyzed by water-soluble palladium(II) complex in water |url=https://pubs.rsc.org/en/content/articlelanding/2009/gc/b900807a |journal=Green Chemistry |language=en |volume=11 |issue=9 |pages=1446–1452 |doi=10.1039/B900807A |issn=1463-9270}}</ref>

2-Nitrotoluene can be ] to yield 2-nitrobenzaldehyde.<ref>{{cite journal|journal=Acta Chim. Slov.|year=2005|volume=52|pages=460–462|title=Synthesis of 2-Nitrobenzaldehyde from 2-Nitrotoluene|author=
Alexander Popkov}} {{Webarchive|url=https://web.archive.org/web/20110605084809/http://acta.chem-soc.si/52/52-4-460.pdf |date=2011-06-05 }}, Alexander Popkov</ref><ref>{{cite journal|journal=Org. Synth.|year=1944|volume=24|page=75|doi= 10.15227/orgsyn.024.0075|title=
o-Nitrobenzaldehyde|author1=S. M. Tsang |author2=Ernest H. Wood |author3=John R. Johnson}}</ref>

Alternatively, 2-nitrotoluene as formed above can be ] to a 2-nitrobenzyl halide followed by ] with ] and ] to yield 2-nitrobenzaldehyde, which is subsequently purified with the creation of a ] adduct.<ref>{{cite web|title=Process for the Preparation of 2-Nitrobenzaldehyde|url=https://patents.google.com/patent/US4297519|access-date=2010-10-18}}</ref>

==Uses==
2-Nitrobenzaldehyde is an intermediate in an early route to ], a water-insoluble dye commonly used to dye jeans and other fabrics. In the ], 2-nitrobenzaldehyde condenses with ] in basic aqueous solution to yield indigo in a one-pot synthesis<ref>{{Cite web |url=http://www.chem.missouri.edu/chem1100/Indigo%20synthesis.doc |title=Indigo Synthesis |access-date=2009-07-18 |archive-url=https://web.archive.org/web/20110720000154/http://www.chem.missouri.edu/chem1100/Indigo%20synthesis.doc |archive-date=2011-07-20 |url-status=dead }}</ref><ref>{{Cite web |url=http://courses.chem.psu.edu/chem36/Chem36H/IndivExpt1/863%20Indigo.pdf |title=Synthesis of Indigo and Vat Dyeing |access-date=2009-07-18 |archive-url=https://web.archive.org/web/20110720032713/http://courses.chem.psu.edu/chem36/Chem36H/IndivExpt1/863%20Indigo.pdf |archive-date=2011-07-20 |url-status=dead }}</ref> The method was abandoned in the early part of the 20th century, being replaced by routes from ].<ref>{{Cite book |url=https://onlinelibrary.wiley.com/doi/book/10.1002/14356007 |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2003-03-11 |publisher=Wiley |isbn=978-3-527-30385-4 |editor-last=Wiley-VCH |edition=1 |language=en |doi=10.1002/14356007.a14_149.pub2|chapter=Indigo and Indigo Colorants}}</ref>
:]{{clear-left}}

Given its two relatively reactive groups, 2-nitrobenzaldehyde is a potential starting material for other compounds. Substituted 2-nitrobenzaldehydes can also be used to yield other important compounds based on indigo, such as ].

2-Nitrobenzaldehyde has been shown to be a useful ] for various functions.<ref>{{cite journal|title=Photochemistry of 2-Nitrobenzylidene Acetals|first1=Peter|last1=Šebej|first2=Tomáš|last2=Šolomek|first3=Ľubica|last3=Hroudná|first4=Pavla|last4=Brancová|first5=Petr|last5=Klán|journal=J. Org. Chem.|year=2009|volume=74|issue=22|pages=8647–8658|doi=10.1021/jo901756r|pmid=19824651}}</ref><ref>{{cite journal|title=Chemical Actinometry: Using o-Nitrobenzaldehyde to Measure Lamp Intensity in Photochemical Experiments|author1=Kristine L. Willett |author2=Ronald A. Hites|journal=J. Chem. Educ.|year=2000|volume=77|issue=7 |pages=900|doi=10.1021/ed077p900|bibcode=2000JChEd..77..900W }}</ref>

==References==
<references/>

{{DEFAULTSORT:Nitrobenzaldehyde, 2-}}
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