메틸리튬
메틸리튬 · 메틸리튬(METHYLLITHIUM) · MELI · LITHIUM METHANIDE · Methyllithium lithium bromide complex solution · Methyllithium solution · Lowhalide · 1-2MinEther
식별자 및 물리적 특성
| CAS No. | 917-54-4 |
|---|---|
| 분자식 | CH3Li |
| 평균 분자량 | 22 g/mol |
| SMILES | [CH3-].[Li+] |
| InChIKey | DVSDBMFJEQPWNO-UHFFFAOYSA-N |
| PubChem CID | 2724049 |
| ChEBI | CHEBI:51486 |
| DTXSID | DTXSID7061273 |
| 현지명 | 메틸리튬 |
화학 및 물리적 성질
| 극성 표면적 | 0 |
|---|---|
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 2 |
| 형식 전하 | 0 |
| 복잡도 | 2 |
| 녹는점 | 70-71℃ |
| 끓는 점 | 88℃ |
| 밀도 | 0.85 g/mL at 20 °C |
| 증기 밀도 | 3 (vs air) |
| 인화점 | 5 °F |
| 저장 조건 | 2-8°C |
| 물리적 상태 | 액체 |
| 비중 | 0.83 |
| 색상 | 무색~황색 |
| 폭발한계 | 1.7-36% (v/v) Information refers to the main component.) |
| 용해도 | 물과 반응합니다. |
| BRN | 3587162 |
| InChI | 1S/CH3.Li/h1H3 |
| InChIKey | DVSDBMFJEQPWNO-UHFFFAOYSA-N |
| SMILES | [Li]C |
| EPA | Lithium, methyl- (917-54-4) |
화학적 성질
Methyllithium is a colorless to yellowish solution, It is insoluble in hydrocarbon solvents although propyllithium and the higher homologues are miscible in hydrocarbons. Methyllithium is soluble in diethyl ether to about 6% by weight at room temperature (with or without lithium bromide) and is a little less soluble in tetrahydrofuran. Cooling of these solutions produces clear, colorless crystals of methyllithium etherate. Methyllithium is stable to about 200°C, at which temperature it disproportionates to dilithiomethane and methane.
안전 및 규제
| 수질 위해 등급(WGK) | 2 |
|---|---|
| TSCA 등재 상태 | TSCA listed |
| 운송 번호(UN) | UN 3399 4.3/PG 1 |
| 관세 코드 | 29319090 |
| 위험 문구(R) | 12-15-17-22-34-66-67-65-51/53-11-36/37/38-36/38-19-40-36/37-37-14/15 |
| 위험 표시 | F+,C,N,F,Xn,Xi |
| 안전 문구(S) | 16-26-36/37/39-45-43-30-60-62-61-36/37 |
| 포장분류 | I |
| 위험 등급 | 4.3Eye Dam. 1Flam. Liq. 2Pyr. Liq. 1Skin Corr. 1BWater-react 1 |
| 기존화학 물질 | KE-24321 |
| F 고인화성물질 | 10 |
| 자연 발화 온도 | 180°C (Information refers to the main component.) |
| 저장 분류 | 4.2 - Pyrophoric and self-heating hazardous materials |
용도
용도
There are no significant industrial uses of methyllithium, but it is widely used in the laboratory in Grignard type reactions. Methyllithium is an organolithium reagent mainly used for deprotonation and as a source of methyl anion. It is a strong base and a strong nucleophile.
제조 및 합성 방법
제조 방법
Methyllithium is produced industrially by the reaction of methyl chloride or methyl bromide with lithium metal dispersion in diethyl ether. The reaction with methyl chloride yields a solution of methyllithium and a precipitate of lithium chloride which may be readily separated. When methyl bromide is used, the lithium bromide byproduct remains in solution and complexes with the methyllithium. This reduces the reactivity of the methyllithium and, in certain cases, affects its usefulness. On the other hand, the less reactive complex is more stable in diethyl ether. Methyllithium produced from methyl chloride contains only about 0.3 % lithium chloride in a 5 % solution in diethyl ether. It is more reactive than the lithium bromide complex, but decomposes at the rate of 1 % of the contained methyllithium per year (that is 5.00 % solution goes to 4.95 %) at room temperature. The decomposition by ether cleavage results in methane and ethylene formation which increases the pressure in the container on long storage. Methyllithium can be prepared easily in tetrahydrofuran but it has a half-life of only about 2 days at room temperature due to solvent cleavage.