1-Chloro-N,N,2-trimethylpropenylamine Chemische Eigenschaften,Einsatz,Produktion Methoden
R-S?tze Betriebsanweisung:
R10:Entzündlich.
R34:Verursacht Ver?tzungen.
S-S?tze Betriebsanweisung:
S16:Von Zündquellen fernhalten - Nicht rauchen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
Chemische Eigenschaften
Colorless to yellow liquid
Verwenden
1-Chloro-
N,
N,2-trimethyl-1-propenylamine is an
acid halogenation reagent developed by Ghosez, that enables the conversion of carboxylic acids into the corresponding chlorides under strictly neutral conditions. This method was successfully used in the total synthesis of caloporoside, roseophilin, (-)-enniatin B, (±)-epimeloscine and (±)-meloscine.
synthetische
1-chloro-N,N,2-trimethylpropenylamine is conveniently prepared by the reaction of N,N,2-
trimethylpropanamide with Phosgene followed by dehydrochlorination of the intermediate α-chloroiminium
chloride (eq 1).
[1,2] Recent unpublished results of our laboratory have shown that Phosphorus Oxychloride or dior triphosgene can also be used for the preparation of TMCE.
Application
1-Chloro-N,N,2-trimethylpropenylamine (TMCE) is used to mild halogenation of alcohols and acids under neutral conditions; conversion of N-protected amino acids into
peptides without racemization; coupling of acids and allylic alcohols with organometallics; [2 + 2]
cycloaddition synthons, more reactive than dimethylketene.
Synthesis Reference(s)
Journal of the American Chemical Society, 94, p. 2869, 1972
DOI: 10.1021/ja00763a061Organic Syntheses, Coll. Vol. 6, p. 282, 1988
Tetrahedron Letters, 25, p. 5043, 1984
DOI: 10.1016/S0040-4039(01)91114-1
1-Chloro-N,N,2-trimethylpropenylamine Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte