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{{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
⚫ |Section1={{Chembox Identifiers
⚫ | CASNo = 552-89-6
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| ChEBI = 66927
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | 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 | InChI = 1/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H
⚫ | SMILES = O=()c1ccccc1C=O
| InChIKey = CMWKITSNTDAEDT-UHFFFAOYAD | InChIKey = CMWKITSNTDAEDT-UHFFFAOYAD
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 166559
| 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>

'''2-Nitrobenzaldehyde''' is an organic ] compound containing a ] ] ortho to ]. 2-Nitrobenzaldehyde once was produced as an intermediate in the synthesis of the popular dye ].


==Synthesis== ==Synthesis==
The main routes to nitrobenzaldehyde begin with the nitration of ] and ] followed by the conversions of the resulting 2-nitrostyrene and 2-nitrocinnamic acids. ] can also be ], e.g. in a solution of ] in ], in high-yield to ].<ref></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>, Bo Feng, Zhenshan Hou, Xiangrui Wang, Yu Hu, Huan Li and Yunxiang Qiao</ref> 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=
In one synthetic process, ] is mono-nitrated at cold temperatures to ], with about 58% being converted to the ortho- isomer, the remaining forming meta- and para- isomers.<ref>http://www.thecatalyst.org/experiments/AndersonS/AndersonS.html Product Distribution in the Nitration of Toluene, Steven W. Anderson, January 7, 1999</ref> The 2-nitrotoluene can then be ] to yield 2-nitrobenzaldehyde.<ref>, Alexander Popkov</ref><ref>{{cite web|title= o-Nitrobenzaldehyde|url=http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0641|work=|archiveurl=http://www.webcitation.org/5iUG3LUdZ|archivedate=2009-07-23|deadurl=no|accessdate=2009-07-21}}</ref>
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=http://www.google.com/patents?hl=en&lr=&vid=USPAT4297519&id=uOwBAAAAEBAJ&oi=fnd&dq=2-nitrobenzyl+bromide&printsec=abstract#v=onepage&q=2-nitrobenzyl%20bromide&f=false|accessdate=2010-10-18|deadurl=no}}</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>

The nitration of ] produces mostly ], with yields being about 19% for the ortho-, 72% for the meta- and 9% for the para isomer.<ref></ref> For this reason, the nitration of benzaldehyde to yield 2-nitrobenzaldehyde is not cost-effective.


==Uses== ==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>See ]</ref><ref></ref><ref></ref><ref></ref> The method was abandoned in the early part of the 20th century, being replaced by routes from ].<ref>Elmar Steingruber “Indigo and Indigo Colorants” Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim. {{DOI| 10.1002/14356007.a14_149.pub2}}</ref> 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}} :]{{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 ]. 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 funcionalities.<ref>Peter Šebej, Tomáš Šolomek, Ľubica Hroudná, Pavla Brancová and Petr Klán: J. Org. Chem., 2009, 74 (22), pp 8647–8658; DOI: 10.1021/jo901756r {{DOI| 10.1021/jo901756r}}</ref> 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==
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{{DEFAULTSORT:Nitrobenzaldehyde, 2-}} {{DEFAULTSORT:Nitrobenzaldehyde, 2-}}
] ]
] ]

]
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Latest revision as of 17:32, 17 November 2024

2-Nitrobenzaldehyde
Skeletal formula of 2-nitrobenzaldehyde
Ball-and-stick model of the 2-nitrobenzaldehyde molecule
Names
Preferred IUPAC name 2-Nitrobenzaldehyde
Other names Nitrobenzaldehyde
ortho-Nitrobenzaldehyde
o-Nitrobenzaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.206 Edit this at Wikidata
EC Number
  • 209-025-3
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5HKey: CMWKITSNTDAEDT-UHFFFAOYSA-N
  • InChI=1/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5HKey: CMWKITSNTDAEDT-UHFFFAOYAD
SMILES
  • O=()c1ccccc1C=O
Properties
Chemical formula C7H5NO3
Molar mass 151.12 g/mol
Appearance Pale yellow crystalline powder
Melting point 43 °C (109 °F; 316 K)
Boiling point 152 °C (306 °F; 425 K)
Solubility in water Insoluble
Magnetic susceptibility (χ) -68.23·10 cm/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Harmful, Potentially mutagenic
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H319, H335, H412
Precautionary statements P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

2-Nitrobenzaldehyde is an organic compound with the formula O2NC6H4CHO. It is one of three isomers of nitrobenzaldehyde. It contains a nitro group adjacent to the formyl group.

Synthesis

The nitration of benzaldehyde produces mostly 3-nitrobenzaldehyde. Partly for this reason, 2-nitrobenzaldehyde is prepared by indirect routes. The main routes to nitrobenzaldehyde begin with the nitration of styrene or cinnamic acid followed by the conversions of the resulting 2-nitrostyrene and 2-nitrocinnamic acids, respectively. Cinnamaldehyde can also be nitrated in high-yield to 2-nitrocinnamaldehyde. This compound is then oxidized to 2-nitrocinnamic acid, which is decarboxylated to the 2-nitrostyrene. The vinyl group can be oxidized in a number of different ways to yield 2-nitrobenzaldehyde.

2-Nitrotoluene can be oxidized to yield 2-nitrobenzaldehyde.

Alternatively, 2-nitrotoluene as formed above can be halogenated to a 2-nitrobenzyl halide followed by oxidation with DMSO and sodium bicarbonate to yield 2-nitrobenzaldehyde, which is subsequently purified with the creation of a bisulfite adduct.

Uses

2-Nitrobenzaldehyde is an intermediate in an early route to indigo, a water-insoluble dye commonly used to dye jeans and other fabrics. In the Baeyer-Drewson indigo synthesis, 2-nitrobenzaldehyde condenses with acetone in basic aqueous solution to yield indigo in a one-pot synthesis The method was abandoned in the early part of the 20th century, being replaced by routes from aniline.

Baeyer-Drewson Indigo Synthesis

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 indigo carmine.

2-Nitrobenzaldehyde has been shown to be a useful photoremovable protecting group for various functions.

References

  1. "2-Nitrobenzaldehyde". pubchem.ncbi.nlm.nih.gov.
  2. Brühne, Friedrich; Wright, Elaine (2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_463.pub2. ISBN 978-3-527-30385-4.
  3. Brühne, Friedrich; Wright, Elaine (2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_463.pub2. ISBN 978-3-527-30385-4.
  4. Robert E. Buckles, M. Peter Bellis (1953). "o-Nitrocinnamaldehyde". Org. Synth. 33: 60. doi:10.15227/orgsyn.033.0060.
  5. Feng, Bo; Hou, Zhenshan; Wang, Xiangrui; Hu, Yu; Li, Huan; Qiao, Yunxiang (2009-09-01). "Selective aerobic oxidation of styrene to benzaldehyde catalyzed by water-soluble palladium(II) complex in water". Green Chemistry. 11 (9): 1446–1452. doi:10.1039/B900807A. ISSN 1463-9270.
  6. Alexander Popkov (2005). "Synthesis of 2-Nitrobenzaldehyde from 2-Nitrotoluene". Acta Chim. Slov. 52: 460–462. Archived 2011-06-05 at the Wayback Machine, Alexander Popkov
  7. S. M. Tsang; Ernest H. Wood; John R. Johnson (1944). "o-Nitrobenzaldehyde". Org. Synth. 24: 75. doi:10.15227/orgsyn.024.0075.
  8. "Process for the Preparation of 2-Nitrobenzaldehyde". Retrieved 2010-10-18.
  9. "Indigo Synthesis". Archived from the original on 2011-07-20. Retrieved 2009-07-18.
  10. "Synthesis of Indigo and Vat Dyeing" (PDF). Archived from the original (PDF) on 2011-07-20. Retrieved 2009-07-18.
  11. Wiley-VCH, ed. (2003-03-11). "Indigo and Indigo Colorants". Ullmann's Encyclopedia of Industrial Chemistry (1 ed.). Wiley. doi:10.1002/14356007.a14_149.pub2. ISBN 978-3-527-30385-4.
  12. Šebej, Peter; Šolomek, Tomáš; Hroudná, Ľubica; Brancová, Pavla; Klán, Petr (2009). "Photochemistry of 2-Nitrobenzylidene Acetals". J. Org. Chem. 74 (22): 8647–8658. doi:10.1021/jo901756r. PMID 19824651.
  13. Kristine L. Willett; Ronald A. Hites (2000). "Chemical Actinometry: Using o-Nitrobenzaldehyde to Measure Lamp Intensity in Photochemical Experiments". J. Chem. Educ. 77 (7): 900. Bibcode:2000JChEd..77..900W. doi:10.1021/ed077p900.
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