abstract from: http://www.nsc.org/library/chemical/aniline.htm (http://www.nsc.org/library/chemical/aniline.htm)
Aniline (CAS #62-53-3) is a colorless to brown oily liquid with an aromatic, pungent odor. It is used in the manufacturing of resins, varnishes, perfumes, printing inks, cloth marking inks, paint removers, photographic chemicals, explosives, herbicides, fungicides, rigid polyurethanes, optical whitening agents, and shoe blacks. It is used as a solvent, and as a chemical intermediate for rubber processing, accelerators, corrosion inhibitors, dyes and pigments, speciality resins, cyclohexylamine, hydroquinine, pesticides such as alachlor, pharmaceuticals such as sulfonamides, 4-anilinophenol, and methylenediisocyanate. It is a component of lacquers, wood stains, and skin stains. It is an analytical reagent in paper chemistry, and an azeotropic agent in the manufacturing of anhydrous hydrazine. It is used in the synthesis of intermediates for artificial sweeteners and isocyanate; it is also a catalyst and stabilizer in the synthesis of hydrogen peroxide and cellulose.
That come up with 2 seconds of looking in google.
It is an analytical reagent in paper chemistry.
Can anybody here elaborate on, paper chemistry? :)
First, a link to org. syn., because we like them best:
http://www.orgsyn.org/orgsyn/prep.asp?rxntypeid=217&prep=CV2P0044 (http://www.orgsyn.org/orgsyn/prep.asp?rxntypeid=217&prep=CV2P0044)
Note that in this modern era, we do not make our hypochlorite by bubbling chlorine gas through NaOH solution, rather we buy it in 5.25 or 15% solutions at the grocery store.
Second, here is a hofmann rearrangement on a delicate substrate using bleach (probably this can be much simplified)
4-(15N)-Amino-2,6-dinitrotoluene
To 5.2 g (20.7 mmol) 3,5-dinitro-4-methylbenz-15N-amide in 250 ml methanol was added 34 mL 5.25% NaOCl (Chlorox) dropwise over a period of 10 min while stirring with a magnetic stir bar. During the addition, the reaction mixture became homogeneous. After the addition, the solution was concentrated to dryness using a vacuum pump at < 30 C. The resulting solid was dissolved in 350 mL water containing 2.5 g NaHCO3 and heated on a steam bath. After 10 min, solid began to precipitate from solution. Heating was continued for 1 hr. The flask was cooled in an ice-water bath and the solid was filtered, washed with water, and dried under vacuum to yield 4.1 g of a brown solid. The solid was dissolved in 30 mL of dioxane and dry HCl was bubbled into the solution. Blah blah, yield 3.5 g, 85%.
this was from J. Labelled. Cpd. Radiopharm. XLI; 1998, 615
More to come on the use of urea, etc.