| Identification | More | [Name]
Lithium acetylide ethylenediamine complex | [CAS]
6867-30-7 | [Synonyms]
LITHIUM ACETYLIDE
LITHIUM ACETYLIDE ETHYLENEDIAMINE COMPLEX
1,2-ethanediamine,compd.withlithiumacetylide(li(c2h))(1:1)
LITHIUM ACETYLIDE-ETHYLENEDIAMINE COMPLE X, 25 WT. % SLURRY IN TOLUENE
Lithiumacetylide,ethylenediaminecomplex,85%
Lithium, (1,2-ethanediamine-.kappa.N,.kappa.N)ethynyl-
LITHIUM ACETYLIDE ETHYLENEDIAMINE COMPLEX: TECH., 90%
lithium acetylene, ethylenediamine complex | [EINECS(EC#)]
229-967-9 | [Molecular Formula]
C4H9LiN2 | [MDL Number]
MFCD00013183 | [Molecular Weight]
92.07 | [MOL File]
6867-30-7.mol |
| Chemical Properties | Back Directory | [Appearance]
slightly yellow to light brown crystals | [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 | [InChIKey]
QJQWXTYPTBEPGS-UHFFFAOYSA-N | [CAS DataBase Reference]
6867-30-7(CAS DataBase Reference) | [EPA Substance Registry System]
6867-30-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
F,C | [Risk Statements ]
R15:Contact with water liberates extremely flammable gases.
R34:Causes burns.
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R63:Possible risk of harm to the unborn child.
R48/20:Harmful: danger of serious damage to health by prolonged exposure through inhalation .
R11:Highly Flammable.
R35:Causes severe burns.
R14/15:Reacts violently with water, liberating extremely flammable gases .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R14:Reacts violently with water. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S16:Keep away from sources of ignition-No smoking .
S7/8:Keep container tightly closed and dry . | [RIDADR ]
UN 3399 4.3/PG 1
| [WGK Germany ]
3
| [F ]
10-21 | [TSCA ]
Yes | [HazardClass ]
4.3 | [PackingGroup ]
III | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
Lithium 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.
| [Uses]
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. | [Uses]
The 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. | [Preparation]
The 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. | [Production Methods]
Lithium 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. |
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