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6867-30-7 - Lithium acetylide ethylenediamine complex, tech. 90% - L12401 - Alfa Aesar

L12401 Lithium acetylide ethylenediamine complex, tech. 90%

CAS Number
6867-30-7
Synonyms

Size Price ($) Quantity Availability
25g 76.00
100g 224.00
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Lithium acetylide ethylenediamine complex, tech. 90%

MDL
MFCD00013183
EINECS
229-967-9

Chemical Properties

Formula
C4H9LiN2
Formula Weight
92.07
Melting point
ca 76° dec.
Density
1.04
Sensitivity
Moisture Sensitive
Solubility
Soluble in ethylene diamine, n-propyl amine, n-butyl amine, pyridine, dimethyl formamaide, diglyme, dioxan and dimethylsulfoxide.

Applications

Lithium 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.

Notes

Moisture and light sensitive. Store in cool place. Incompatible with alcohols, acids, oxidizing agents, water. It reacts with water to form lithium hydroxide and acetylene, which is a flammable gas. Over time, pressure may increase causing containers to burst. Handle and open container with care.

Literature References

Convenient, relatively stable form of lithium acetylide, soluble in organic solvents such as DMF, DMSO, diglyme and dioxan: J. Org. Chem., 28, 2775 (1963); 29, 1872 (1964). For addition to ketones to give ethynyl carbinols, see: J. Org. Chem., 30, 1604 (1965). For reaction with alkyl halides in DMSO to give terminal alkynes, see: Can. J. Chem., 41, 2600 (1963).

Hashimoto, K.; Kumagai, N.; Shibasaki, M. A Carbon Nanotube Confinement Strategy to Implement Homogeneous Asymmetric Catalysis in the Solid Phase. Chem. Eur. J. 2015, 21 (11), 4262-4266.

Bassan, E. M.; Baxter, C. A.; Beutner, G. L.; Emerson, K. M.; Fleitz, F. J.; Johnson, S.; Keen, .; Kim, M. M.; Kuethe, J. T.; Leonard, W. R.; Mullens, P. R.; Muzzio, D. J.; Roberge, C.; Yasuda, N. Multikilogram-Scale Synthesis of a Chiral Cyclopropanol and an Investigation of the Safe Use of Lithium Acetylide-Ethylene Diamine Complex. Org. Process Res. Dev. 2011, 16 (1), 87-95.

GHS Hazard and Precautionary Statements

Hazard Statements: H261-H314-H318

In contact with water releases flammable gas. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P280-P305+P351+P338-P310a-P370+P378i-P403-P402+P404

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor In case of fire: Use for extinction: Fire-extinguishing powder. Store in a well-ventilated place. Store in a dry place. Store in a closed container.

Other References

Beilstein
3593824
Hazard Class
4.3
Packing Group
I
Harmonized Tariff Code
2931.90
TSCA
Yes

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