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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Miscible with water, ethanol, ether, acetone, chloroform, benzene and alkaline.
Notes
Incompatible with strong oxidizing agents, Strong acids, acid chlorides, acid anhydrides, chloroformates and halogens.
RUO – Research Use Only
General References:
- 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.