Bredereck's Reagent
Title: Bredereck's Reagent
CAS Registry Number: 5815-08-7
CAS Name: 1-(1,1-Dimethylethoxy)-N,N,N¢,N¢-tetramethylmethanediamine
Additional Names: bis(dimethylamino)-tert-butyloxymethane; tert-butoxybis(dimethylamino)methane; tert-butoxy-N,N,N¢,N¢-tetramethylmethanediamine
Molecular Formula: C9H22N2O
Molecular Weight: 174.28
Percent Composition: C 62.02%, H 12.72%, N 16.07%, O 9.18%
Literature References: Aminal ester used in condensation reactions. Prepn: H. Bredereck et al., Angew. Chem. Int. Ed. 6, 356 (1967); idem et al., Ber. 101, 41 (1968). Synthetic applications: B. M. Trost, M. Preckel, J. Am. Chem. Soc. 95, 7862 (1973); W. Haefliger, H. Knecht, Tetrahedron Lett. 25, 285 (1983); J.-P. Vors, J. Heterocycl. Chem. 28, 1043 (1991); A. C. Spivey et al., J. Org. Chem. 65, 5253 (2000); E. Morera et al., Org. Lett. 4, 1139 (2002); S. Csihony et al., Adv. Synth. Catal. 346, 1081 (2004). Review: W. Kantlehner, J. Prakt. Chem. Chem.-Ztg. 337, 418-421 (1995).
Properties: bp10-12 48-52°. bp15 50-55°. nD20 1.4260.
Boiling point: bp10-12 48-52°; bp15 50-55°
Index of refraction: nD20 1.4260
Use: Mild enamination reagent; catalyst in ring-opening polymerization reactions.

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