2-Nitrochlorobenzene

2-Chlornitrobenzol.svg 150px 1-Chloro-2-nitrobenzene 2-Chloronitrobenzene 13853953 C1=CC=C(C(=C1)[N+](=O)[O-])Cl 1/C6H4ClNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H BFCFYVKQTRLZHA-UHFFFAOYAA 1S/C6H4ClNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H BFCFYVKQTRLZHA-UHFFFAOYSA-N 88-73-3 34270 6945 201-854-9 CZ0875000 1578 D1YI9R2K8O C14407 53330 1 6 4 1 2 Yellow crystals 1.368 g/mL 33 245.5 Insoluble Highly soluble in diethyl ether, benzene, and hot ethanol other solvents 06 07 08 09 Danger 301 302 311 312 317 331 332 350 351 361 372 411 201 202 260 261 264 270 271 272 273 280 281 301+310 301+312 302+352 304+312 304+340 308+313 311 312 314 321 322 330 333+313 361 363 391 403+233 405 501 Toxic, Irritant 124 2-Nitrochlorobenzene is an organic compound with the formula ClC6H4NO2. It is one of three isomeric nitrochlorobenzenes.10.1002/14356007.a17_411 Nitro Compounds, Aromatic Ullmann's Encyclopedia of Industrial Chemistry 2000 Booth Gerald 978-3-527-30385-4 Wiley-VCH Weinheim It is a yellow crystalline solid that is important as a precursor to other compounds due to its two functional groups. Synthesis Nitrochlorobenzene is typically synthesized by nitration of chlorobenzene in the presence of sulfuric acid: C6H5Cl + HNO3 → O2NC6H4Cl + H2O This reaction affords a mixture of isomers. Using an acid ratio of 30% nitric acid, 56% sulfuric acid and 14% water, the product mix is typically 34-36% 2-nitrochlorobenzene and 63-65% 4-nitrochlorobenzene, with only about 1% 3-nitrochlorobenzene. Reactions 2-Nitrochlorobenzene can be reduced to the 2-chloroaniline with Fe/HCl mixture, the Bechamp reduction. 2-Nitrochlorobenzene, like its isomers, is reactive toward nucleophiles, resulting in chloride substitution. With polysulfide, it reacts to give di-orthonitrophenyl disulfide:10.15227/orgsyn.008.0064 free Di-o-Nitrophenyl Disulfide Organic Syntheses 1928 8 64 Marston T. Bogert Arthur Stull 2 O2NC6H4Cl + Na2S2 -> (O2NC6H4S)2 + 2 NaCl Similarly, it reacts with sodium methoxide to give 2-nitroanisole. Substitution of chloride by fluoride is also practiced commercially to convert 2-nitrochlorobenzene to 2-fluoronitrobenzene. The Halex process uses potassium fluoride in polar solvents like sulfolane : O2NC6H4Cl + KF -> O2NC6H4F + KCl Applications 2-Nitrochlorobenzene is useful because both of its reactive sites can be utilized to create further compounds that are mutually ortho. Its derivative 2-chloroaniline is a precursor to 3,3’-dichlorobenzidine, a precursor to dyes and pesticides. Some of the recognized uses of 2-nitrochlorobenzene include in the synthesis loxapine,((Lednicer, D.)) 2009 Strategies for organic drug synthesis and design Wiley 2nd 9780470190395 quetiapine,((Saadatjoo, N.)), ((Javaheri, M.)), ((Saemian, N.)), ((Amini, M.)) Journal of Radioanalytical and Nuclear Chemistry Synthesis of 11-14C-quetiapine, 11-14C-isoclotiapine and 10-(4-methylpiperazin-1-yl)pyrido[4,3-b][1,4]benzothiazepine[10-14C] 310 1 433–439 October 2016 http://link.springer.com/10.1007/s10967-016-4798-1 10.1007/s10967-016-4798-1 28 August 2026 subscription amoxapine,((Castañer, J.)), ((Playle, A. C.)) Drugs of the Future Amoxapine 1 11 511 1976 http://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=313544&p_IsPs=N 0377-8282 10.1358/dof.1976.001.11.313544 28 August 2026 subscription clotiapine, metiapine & methopromazine.Charpentier, P. et al, C.R. Hebd. Seances Acad. Sci., 1952, 235, 59. References Category:Nitrobenzene derivatives Category:2-Chlorophenyl compounds