Lithium acetylide ethylenediamine complex

Lithium acetylide ethylenediamine complex Basic information
Product Name:Lithium acetylide ethylenediamine complex
Synonyms:LITHIUM ACETYLIDE-ETHYLENEDIAMINE COMPLE X, 25 WT. % SLURRY IN TOLUENE;1,2-ethanediamine,compd.withlithiumacetylide(li(c2h))(1:1);Lithium, (1,2-ethanediamine-.kappa.N,.kappa.N)ethynyl-;LITHIUM ACETYLIDE ETHYLENEDIAMINE COMPLEX: TECH., 90%;lithium acetylene, ethylenediamine complex;LithiuM acetylide ethylenediaMine coMplex, 85% 50GR;LithiuM acetylide ethylenediaMine coMplex, 25 wt.% slurry in toluene, AcroSeal;LITHIUM ACETYLIDE-ETHYLENEDIAMINE COMPLE
CAS:6867-30-7
MF:C4H7LiN2
MW:90.05
EINECS:229-967-9
Product Categories:Chemical Synthesis;Organometallic Reagents;Alkynyl;Organolithium;Organometallic Reagents
Mol File:6867-30-7.mol
Lithium acetylide ethylenediamine complex Structure
Lithium acetylide ethylenediamine complex Chemical Properties
Melting point 76 °C (dec.)
Boiling point 110.6 °C (lit.)
density 1,04 g/cm3
Fp 7 °F
storage temp. 2-8°C
solubility Soluble in ethylene diamine, n-propyl amine, n-butyl amine, pyridine, dimethyl formamaide, diglyme, dioxan and dimethylsulfoxide.
form Crystals or Crystalline Powder
color Slightly yellow to light brownor
Sensitive Moisture Sensitive
BRN 3593824
InChIKeyQJQWXTYPTBEPGS-UHFFFAOYSA-N
CAS DataBase Reference6867-30-7(CAS DataBase Reference)
EPA Substance Registry SystemLithium, (1,2-ethanediamine-.kappa.N,.kappa.N')ethynyl- (6867-30-7)
Safety Information
Hazard Codes F,C
Risk Statements 15-34-67-65-63-48/20-11-35-14/15-20/21/22-14
Safety Statements 26-43-45-62-36/37/39-43B-16-6A-7/8-3/7/9
RIDADR UN 3399 4.3/PG 1
WGK Germany 3
10-21
TSCA Yes
HazardClass 4.3
PackingGroup III
HS Code 38249095
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Lithium acetylide ethylenediamine complex Usage And Synthesis
Chemical PropertiesLithium Acetylide Ethylenediamine Complex is a slightly yellow to light brown crystals, Lithium acetylide is an unstable solid which disproportionates to form lithium carbide (dilithium acetylide) and acetylene. It is soluble in liquid ammonia at its boiling point to the extent of just over one mole per liter. It is not sensitive to shock and presents a hazard due only to possible caustic burns and the hazards presented by ammonia and acetylene, which form when the material contacts the air.
Uses
  • Lithium acetylide, ethylenediamine complex is a general reagent to synthesize ethynylated ketones.
  • It is used as a ligand in the coordination chemistry to synthesize transition metal complexes such as 1-alkynyl-dimethyl(triorganophosphine)gold(III) complex.
  • It is employed in the ring opening reaction of epoxides, as in the total synthesis of (?)-goniotrionin and englerin A.
  • It can also be used in the ethynylation of alkyl halides to prepare terminal alkynes.

UsesThe largest industrial use of lithium acetylide is in the production of vitamin A. It is used to ethynylate methyl vinyl ketone to produce a tertiary carbinol, an intermediate in the multistep synthesis.
A second industrial use is in the production of Placidyl®, a tranquilizer . In this case it is used to ethynylate methyl beta-chloro vinyl ketone. Lithium acetylide is used extensively in the laboratory, mostly for the ethynylation of ketones.
Lithium acetylide is not an article of commerce since it is unstable and cannot be shipped.

UsesLithium acetylide ethylenediamine complex is used in the synthesis of a chiral cyclopropanol. It is also used as an alkynylating reagent for the enantioselective alkynylation of ketones catalyzed by lithium binaphtholate without using other metal sources.
Production MethodsLithium acetylide is produced both in the laboratory and industrially by dissolving lithium metal in refluxing liquid ammonia and then bubbling acetylene into the solution. The solution of monolithium acetylide thus formed is stabilized by the complexing of the lithium ion with ammonia forming a polar acetylenic anion which does not react further with lithium metal. However, if the reaction is carried out in tetrahydrofuran, for example, the lithium acetylide reacts further with lithium to form dilithium acetylide (lithium carbide). In fact, if the ammonia is removed from a solution of lithium acetylide, it disproportionates to dilithium acetylide and acetylene.
PreparationThe ethylenediamine complex of lithium acetylide is produced by allowing lithium metal to react with ethylenediamine in benzene at reflux to form AMithioethylenediamine: H2NCH2CH2NH2+Li -> L1HNCH2CH2NH2+05H2.
Lithium acetylide ethylenediamine complex Preparation Products And Raw materials
Preparation Products1-ethynyl-2-methyl penten-2-ol
barium acetylide SODIUM ACETYLIDE ETHYNYLMAGNESIUM BROMIDE (METHYLDIPHENYLSILYL)ACETYLENE DI-SODIUM ACETYLIDE ETHYNYL(PHENYL)IODONIUM TETRAFLUOROBORATE ETHYNYLMAGNESIUM CHLORIDE Ethylenediamine N,N,N',N'-Tetramethylethylenediamine Lithium acetylide ethylenediamine complex Ethylenediamine dihydrochloride Tetraacetylethylenediamine 2-(2-Aminoethylamino)ethanol N-(1-Naphthyl)ethylenediamine dihydrochloride Lithium carbonate Methyllithium Lithium Lithium chloride

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