2-Nitrobenzaldehyde

changed 477214862 2-nitrobenzaldehyde.svg 125 Skeletal formula of 2-nitrobenzaldehyde 2-Nitrobenzaldehyde-3D-balls.png 135 Ball-and-stick model of the 2-nitrobenzaldehyde molecule 2-Nitrobenzaldehyde Nitrobenzaldehydeortho-Nitrobenzaldehydeo-Nitrobenzaldehyde 552-89-6 correct CAS 66927 correct EBI 166559 correct chemspider 10630 209-025-3 11101 correct FDA 48B18Q9B8E 1/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H CMWKITSNTDAEDT-UHFFFAOYAD correct chemspider 1S/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H correct chemspider CMWKITSNTDAEDT-UHFFFAOYSA-N O=[N+]([O-])c1ccccc1C=O C7H5NO3 151.12 g/mol Pale yellow crystalline powder 43 152 Insoluble −68.23·10−6 cm3/mol Harmful, Potentially mutagenic 2-Nitrobenzaldehyde https://pubchem.ncbi.nlm.nih.gov/compound/11101#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov en 07 Warning 302 315 319 335 412 261 264 270 271 273 280 301+312 302+352 304+340 305+351+338 312 330 332+313 337+313 362 403+233 405 501 2 1 0 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.10.1002/14356007.a03_463.pub2 Benzaldehyde Ullmann's Encyclopedia of Industrial Chemistry 2011 Brühne Friedrich Wright Elaine 978-3-527-30385-4 Synthesis The nitration of benzaldehyde produces mostly 3-nitrobenzaldehyde. Partly for this reason, 2-nitrobenzaldehyde is prepared by indirect routes.10.1002/14356007.a03_463.pub2 Benzaldehyde Ullmann's Encyclopedia of Industrial Chemistry 2011 Brühne Friedrich Wright Elaine 978-3-527-30385-4 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.Org. Synth. 1953 33 60 10.15227/orgsyn.033.0060 free o-Nitrocinnamaldehyde Robert E. Buckles, M. Peter Bellis 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.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 https://pubs.rsc.org/en/content/articlelanding/2009/gc/b900807a Green Chemistry en 11 9 1446–1452 10.1039/B900807A 1463-9270 subscription 2-Nitrotoluene can be oxidized to yield 2-nitrobenzaldehyde.Acta Chim. Slov. 2005 52 460–462 Synthesis of 2-Nitrobenzaldehyde from 2-Nitrotoluene Alexander Popkov http://acta.chem-soc.si/52/52-4-460.pdf 2011-06-05 2009-07-18 https://web.archive.org/web/20110605084809/http://acta.chem-soc.si/52/52-4-460.pdf dead, Alexander PopkovOrg. Synth. 1944 24 75 10.15227/orgsyn.024.0075 free o-Nitrobenzaldehyde S. M. Tsang Ernest H. Wood John R. Johnson 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.Process for the Preparation of 2-Nitrobenzaldehyde https://patents.google.com/patent/US4297519 2010-10-18 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–Drewsen indigo synthesis, 2-nitrobenzaldehyde condenses with acetone in basic aqueous solution to yield indigo in a one-pot synthesishttp://www.chem.missouri.edu/chem1100/Indigo%20synthesis.doc Indigo Synthesis 2009-07-18 https://web.archive.org/web/20110720000154/http://www.chem.missouri.edu/chem1100/Indigo%20synthesis.doc 2011-07-20 dead http://courses.chem.psu.edu/chem36/Chem36H/IndivExpt1/863%20Indigo.pdf Synthesis of Indigo and Vat Dyeing 2009-07-18 https://web.archive.org/web/20110720032713/http://courses.chem.psu.edu/chem36/Chem36H/IndivExpt1/863%20Indigo.pdf 2011-07-20 dead The method was abandoned in the early part of the 20th century, being replaced by routes from aniline.https://onlinelibrary.wiley.com/doi/book/10.1002/14356007 Ullmann's Encyclopedia of Industrial Chemistry 2003-03-11 Wiley 978-3-527-30385-4 Wiley-VCH 1 en 10.1002/14356007.a14_149.pub2 Indigo and Indigo Colorants 450px|thumb|left|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.Photochemistry of 2-Nitrobenzylidene Acetals Peter Šebej Tomáš Šolomek Ľubica Hroudná Pavla Brancová Petr Klán J. Org. Chem. 2009 74 22 8647–8658 10.1021/jo901756r 19824651Chemical Actinometry: Using o-Nitrobenzaldehyde to Measure Lamp Intensity in Photochemical Experiments Kristine L. Willett Ronald A. Hites J. Chem. Educ. 2000 77 7 900 10.1021/ed077p900 2000JChEd..77..900W Drug uses of 2-nitrobenzaldehyde: Mepixanox (Pimexone), Nifedipine, Encainide, Iferanserin, Aranidipine, Nisoldipine, DHP-218, Mdl-72567. References Category:Benzaldehydes Category:Nitrobenzene derivatives