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N,N-Dimethylaniline acts as a precursor to triarylmethane dyes such as crystal violet and malachite green. It is also used in the synthesis of vanillin, methyl violet, and Michler's ketone. Further, it is used as a hardener for plastic resins and an acid scavenger in the manufacture of semisynthetic penicillins and cephalosporins. In addition to this, it is used as a promoter in the curing of polyester and vinyl ester resins.
Base for acylation reactions; see, e.g.: Org. Synth. Coll., 3, 142 (1955), 4, 263 (1963); 5, 171 (1973).
For an example of ortho-lithiation, followed by Pd-catalyzed coupling wth a vinyl bromide, see: Org. Synth. Coll., 7, 172 (1990).
The AlCl3 complex with has been used to cleave benzyl and allyl ethers: Tetrahedron Lett., 32, 1321 (1991).
Brown, T. A.; Chen, H.; Zare, R. N. Detection of the Short-Lived Radical Cation Intermediate in the Electrooxidation of N, N-Dimethylaniline by Mass Spectrometry. Angew. Chem. Int. Ed. 2015, 127 (38), 11335-11337.
Watode, B. D.; Hudge, P. G.; Shinde, M. N.; Talware, R. B.; Kumbharkhane, A. C. Dielectric relaxation study of aniline, N-methylaniline and N,N-dimethylaniline and alcohol in 1, 4-dioxane using picosecond time-domain reflectometry. Phys. Chem. Liq. 2015, 53 (2), 252-263.
Hazard Statements: H227-H301-H311-H331-H351
Combustible liquid. Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Suspected of causing cancer.
Precautionary Statements: P210u-P201-P261-P301+P310a-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER/doctor Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.