2-Nitroaniline

changed changed 477214789 2-Nitroaniline 2-nitroaniline chemical structure.png 130 Skeletal formula of 2-nitroaniline 2-Nitroaniline-3D-balls.png 130 Ball-and-stick model of the 2-nitroaniline molecule 2-Nitroaniline 2-Nitroaniline ortho-Nitroanilineo-Nitroaniline correct chemspider correct CAS 88-74-4 correct EBI 274009 13853943 6946 201-855-4 BY6650000 1661 2519U0541L O=[N+]([O-])c1ccccc1N 1/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 DPJCXCZTLWNFOH-UHFFFAOYAV changed chemspider 1S/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 changed chemspider DPJCXCZTLWNFOH-UHFFFAOYSA-N 6 6 2 2 Orange solid 1.442 g/ml 71.5 284 0.117 g/100 ml (20°C) (SIDS) −0.3 (of anilinium salt) −66.47·10−6 cm3/mol 06 08 Danger 301 311 331 373 412 260 261 264 270 271 273 280 301+310 302+352 304+340 311 312 314 321 322 330 361 363 403+233 405 501 168 3-Nitroaniline, 4-Nitroaniline 2-Nitroaniline is an organic compound with the formula H2NC6H4NO2. It is a derivative of aniline, carrying a nitro functional group in position 2.http://msds.chem.ox.ac.uk/NI/o-nitroaniline.html Safety data for o-nitroaniline 2011-01-17 2009-06-28 https://web.archive.org/web/20090628152854/http://msds.chem.ox.ac.uk/NI/o-nitroaniline.html dead It is mainly used as a precursor to o-phenylenediamine. Synthesis 2-Nitroaniline is prepared commercially by the reaction of 2-nitrochlorobenzene with ammonia: ClC6H4NO2 + 2 NH3 → H2NC6H4NO2 + NH4Cl Many other methods exist for the synthesis of this compound. Direct nitration of aniline is inefficient since anilinium is produced instead. Nitration of acetanilide gives only traces of 2-nitro isomer is obtained due to the great steric effect of the amide. Sulfonation is usually used to block the 4 position and increases the effectiveness to 56%.Organic chemistry T. W. Grahan Solomons Craig B. Fryhle Scott A. Snyder 2011 978-1119077251 11 606–607 John Wiley & Sons Louis Ehrenfeld, Milton Puterbaugh 10.15227/orgsyn.009.0064 free o-Nitrianiline Organic Syntheses 1929 9 64 alt=|center|thumb|488x488px|Laboratory routes to produce 2-nitroaniline Uses and reactions 2-Nitroaniline is the main precursor to phenylenediamines, which are converted to benzimidazoles, a family of heterocycles that are key components in pharmaceuticals.Gerald Booth Nitro Compounds, Aromatic 2007 10.1002/14356007.a17_411 thumb|left|142px|Intramolecular hydrogen-bonding results in a very low basicity for 2-nitroaniline. Aside from its reduction to phenylenediamine, 2-nitroaniline undergoes other reactions anticipated for aromatic amines. It is protonated to give the anilinium salts. Owing to the influence of the nitro substituent, the amine exhibits a basicity nearly 100,000x lower than aniline itself. Diazotization gives diazonium derivative,1,2,3-Benzothiadiazole 1,1-Dioxide G. Wittig R. W. Hoffmann Org. Synth. 1967 47 4 10.15227/orgsyn.047.0004 free which is a precursor to some diazo dyes. Acetylation affords 2-nitroacetanilide. See also 3-Nitroaniline 4-Nitroaniline References External links Analysis of 2-Nitroaniline https://web.archive.org/web/20140808035151/http://faculty.ycp.edu/~jforesma/educ/pchem/stojowski/ona.htm 2014-08-08 Category:2-Aminophenyl compounds Category:Nitrobenzene derivatives