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Trimethylacetyl chloride is used as a precursor in the preparation of tert-butyl peroxypivalate, guttiferon A derivatives, which is potential for the treatment of malaria. It is used as a raw material in the production of synthetic acidamide medicament and phenol ester medicament. In addition to this, it is used for the synthesis of active pharmaceutical ingredients such as aminobenzylpenicilin, cephalexin, cefazolin, dipivefrin and dipivalyl epinephrine. It is also used in heavy polymerization, N-acylating agent for amines, Schiff bases, pyrrolidinones as well as an O-acylating agent for alcohols, lactones and saccharides.
Reacts with sodium formate to give the mixed formic pivalic anhydride, a highly effective reagent for N-formylation: Rec. Trav. Chim., 101, 460 (1982). Similarly, has been used to form mixed anhydrides, particularly of N-protected amino acids and peptides, prior to coupling: Coll. Czech. Chem. Commun., 27, 1273 (1962). The sterically-hindered nature of the pivaloyl group greatly reduces attack at the 'wrong' carbonyl group. For peptide reagents, see Appendix 6.
Has also been used as a reagent for protection of alcohols as their pivaloyl (Pv) esters, allowing selective acylation of a primary over a secondary alcohol: Synthesis, 453 (1986); selective protection of the less hindered of two primary alcohols is possible: J. Chem. Soc., Chem. Commun., 354 (1988). See also Trimethylacetic anhydride, B22983. Cleavage is by room temperature basic hydrolysis: Tetrahedron Lett., 317 (1973); 3561 (1979); J. Org. Chem., 42, 918 (1977), or methanolysis: J. Am. Chem. Soc., 112, 3693 (1990), or a number of other methods, including aqueous methylamine: Tetrahedron, 24, 639 (1968).
In the presence of Cu(I) halides, reacts with Grignard and organolithium reagents to give t-butyl ketones: Tetrahedron Lett., 829 (1971).
Activates heteroaromatic amines to ring-lithiation. For example: Synthesis, 670 (1986):
Moon, S. Y.; Jung, S. H.; Kim, U. B.; Kim, W. S. Synthesis of ketones via organolithium addition to acid chlorides using continuous flow chemistry. RSC Adv. 2015, 5 (97), 79385-79390.
Frömmel, J.; Šebela, M.; Demo, G.; Lenobel, R.; Pospíšil, T.; Soural, M.; Kopečný, D. N-acyl-µ-aminoaldehydes are efficient substrates of plant aminoaldehyde dehydrogenases. Amino Acids 2015, 47 (1), 175-187.
Mentions de danger (UE): H225-H302-H330-H314-H318
Highly flammable liquid and vapour. Harmful if swallowed. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.
Mentions de prudence: P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501a
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.