All Photos(3)

186155

Sigma-Aldrich

Lithium acetylide, ethylenediamine complex

90%

Linear Formula:
LiC≡CH · NH2CH2CH2NH2
CAS Number:
Molecular Weight:
92.07
Beilstein:
3593824
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

90%

bp

110.6 °C (lit.)

mp

76 °C (dec.)

storage temp.

2-8°C

SMILES string

[Li]C#C.NCCN

InChI

1S/C2H8N2.C2H.Li/c3-1-2-4;1-2;/h1-4H2;1H;

InChI key

QJQWXTYPTBEPGS-UHFFFAOYSA-N

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Related Categories

Application

  • 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.

Packaging

10, 50, 100 g in glass bottle

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - Water-react. 2

Supplementary Hazards

Storage Class Code

4.3 - Hazardous materials, which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Preparation, structure and decomposition of gold (I) and gold (III) acetylide complexes.
Schuster O, et al.
Inorgorganica Chimica Acta, 358(5), 1429-1441 (2005)
A formal synthesis of (?)-englerin A by relay ring closing metathesis and transannular etherification.
Lee J and Parker K A
Organic Letters, 14(11), 2682-2685 (2012)
Lithium Acetylide
Midland M M.
e-EROS Encyclopedia of Reagents for Organic Synthesis (2001)
Total Synthesis of (?)-Goniotrionin.
Dias L C and Ferreira M A
The Journal of Organic Chemistry, 77(8), 4046-4062 (2012)
Lithium Acetylide
Midland M M.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)

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