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186155

Sigma-Aldrich

Lithium acetylide, ethylenediamine complex

90%

Synonym(s):

Lithium acetylide ethylenediamine complex, Lithium acetylide, compd. with 1,2-ethanediamine

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About This Item

Linear Formula:
LiC≡CH · NH2CH2CH2NH2
CAS Number:
6867-30-7
Molecular Weight:
92.07
Beilstein:
3593824
EC Number:
229-967-9
MDL number:
MFCD00013183
UNSPSC Code:
12352103
PubChem Substance ID:
24851204
NACRES:
NA.22

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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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.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H261,H314

Hazard Classifications

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

Supplementary Hazards

EUH014

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

Certificates of Analysis (COA)

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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)
Multikilogram-Scale Synthesis of a Chiral Cyclopropanol and an Investigation of the Safe Use of Lithium Acetylide?Ethylene Diamine Complex.
Bassan E M, et al.
Organic Process Research & Development, 16(1), 87-95 (2011)
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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Articles

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