Propynyl lithium

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Structural formula
Structural formula of propynyl lithium
General
Surname Propynyl lithium
other names
  • 1-propynyl lithium
  • Prop-1-in-1-yllithium
Molecular formula C 3 H 3 Li
External identifiers / databases
CAS number 4529-04-8
ECHA InfoCard 100.022.604
PubChem 78287
Wikidata Q17190955
properties
Molar mass 46.00 g mol −1
solubility
  • soluble in ammonia
  • partially soluble in THF and ether
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Propynylithium is a chemical compound from the group of organolithium compounds .

Extraction and presentation

Propynylithium is produced in situ under nitrogen by reacting propyne (condensed in cold tetrahydrofuran ) with n -butyllithium in tetrahydrofuran at −78 ° C or lithium amide in ether / liquid ammonia below −50 ° C or by reacting 1,2-dibromopropane with 3 equivalents Lithium diisopropylamide (double elimination of hydrogen bromide and deprotonation) produced at −60 ° C to 0 ° C in tetrahydrofuran.

Some syntheses start directly with 1-bromopropene .

use

Propynylithium is used in organic synthesis as the nucleophilic source of the propynyl moiety for many electrophiles.

Individual evidence

  1. ↑ a b c d N. Greeves: Propynyllithium . In: Encyclopedia of Reagents for Organic Synthesis , 2001. doi : 10.1002 / 047084289X.rp277
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Gordon W. Gribble, H. Howard Joyner, Frank L. Switzer: Convenient Generation of 1-Propynyllithium. One-Pot Synthesis of Acetylenic Carbinols from 1,2-Dibromopropane and Aldehydes and Ketones. In: Synthetic Communications. 22, 1992, p. 2997, doi : 10.1080 / 00397919208021126 .
  4. ↑ Jean Suffert, Dominique Toussaint: GENERATION OF 1-PROPYNYLLITHIUM FROM (Z / E) -1-BROMO-1-PROPENE: 6-PHENYLHEX-2-YN-5-EN-4-OL. In: Organic Syntheses. 76, 1999, p. 214, doi : 10.15227 / orgsyn.076.0214 .
  5. ^ Jean Suffert, Dominique Toussaint: An Easy and Useful Preparation of Propynyllithium from (Z / E) -1-Bromopropene. In: The Journal of Organic Chemistry. 60, 1995, p. 3550, doi : 10.1021 / jo00116a051 .