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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Preparation, structure and decomposition of gold (I) and gold (III) acetylide complexes.
Schuster O, et al.
Inorgorganica Chimica Acta, 358(5), 1429-1441 (2005)
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)
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)
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