L00431 N,N-Dimethylformamide di-tert-butyl acetal, tech. 90%
SDS
N,N-Dimethylformamide di-tert-butyl acetal, tech. 90%
Chemical Properties
Applications
N,N-Dimethylformamide di-tert-butyl acetal is used as a reagent in the synthesis of (S)-2-(1-tert-butoxycarbonyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}ethylamino)benzoic acid methyl ester, 3-O-tert-butylmorphine, tert-butylesters of pyrrole and indolecarboxylic acids. Further, it is used in the preparation of indolizines by intermolecular cyclization of picolinium salts.
Notes
Literature References
The conversion of carboxylic acids to their esters using DMF acetals (see for example, N,N-Dimethylformamide dimethyl acetal, A15350 ) can be extended to the preparation of t-butyl esters by using excess reagent in benzene or toluene as solvent: Synthesis, 135 (1983).
Gatineau, D.; Nguyen, D. H.; Hérault, D.; Vanthuyne, N.; Leclaire, J.; Giordano, L.; Buono, G. H-adamantylphosphinates as universal precursors of P-stereogenic compounds. J. Org. Chem. 2015, 80 (8), 4132-4141.
Hoecker, J.; Liffert, R.; Burch, P.; Wehlauch, R.; Gademann, K. Caged retinoids as photoinducible activators: Implications for cell differentiation and neurite outgrowth. Org. Biomol. Chem. 2013, 11 (20), 3314-3321.
GHS Hazard and Precautionary Statements
Hazard Statements: H226-H315-H319-H335
Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.
