简介
氢化锂, 氢化铝锂,硼氢化钠,三乙基硼氢化锂(Super Hydride)/钠/钾 ,三仲丁基硼氢化锂( L-Selectride)/钠/钾(K-Selectride),Lithium Trisiamylborohydride (LiBSia3H) 60217-34-7, 三叔丁氧基氢化铝锂,77299-63-9 Lithium diisobutyl-tert-butoxyaluminum hydride solution,Diisobutylaluminum hydride, DIBAL,硼烷四氢呋喃,氨基硼烷等, 金属氢化物,作为还原剂和负氢离子的来源,广泛用于无机和有机合成中,以及作为储氢材料应用到日常生产生活中。金属氢化物还原剂,可以还原取代卤代物到烷烃,醛酮环氧亚胺等到醇或胺,羧酸衍生物如酯,腈及其他衍生物到特别是某些烃基取代的金属化合物,具有反应条件温和,副反应少以及产率高的优点,体现出较好的化学选择性和立体 选择性。在复杂的天然产物,药物分子的合成中,较之其他还原法显示出更多的优点。
应用举例
1. 还原卤代物等到相应的烷烃(反应式A,B),并且氘代实验表明,该还原反应经过明确的SN2取代机理(反应式B)。另外,OTs,OMs等取代基也能被还原。

2. 还原环氧到醇,在如下例中,三乙基硼氢化锂比的四氢铝锂的选择性要高很多。

3. 选择性还原醛酮到相应的醇。在α-环己酮的还原中,以很高的选择性的得到顺势的产品(反应式D);并且在醛和酮同时存在的情况下,可以优先还原醛到相应的一级醇(反应式E)。其中,Lithium trisiamylborohydride (LiBSia3H)表现出更好的选择性,以其他取代的环己酮为例,各氢化物还原总结如表一。
4. 选择性的还原羧酸及其衍生物。可以在有其他可被还原的基团存在下,选择性的还原酯基。
5.其他用途。氢化物也可以转移负氢离子到其他的过度金属有机化合物上,形成新的M-H化合物,选择性的脱除甲基。
参考文献
l Lithium Triethyllborohydride,Marek Zaidlewicz,Herbert C. Brown, Encyclopedia of Reagents for Organic Synthesis,2001
l Krishnamutthy, S. Schubert R.M Brown, H, C, J., Am Chem. Soc 1973, 95, 8486
l JACS, 1973
Chemical Name | Lithium hydride |
Synonym |
Hydrure de lithium
LITHIUM HYDRIDE
LITHIUM HYDRIDE 98% &
LITHIUM HYDRIDE , -30 MESH
LITHIUM HYDRIDE, PIECES
LITHIUM HYDRIDE, POWDER
LITHIUM HYDRIDE, POWDER, -30 MESH, 95%
LiH
Lithium Hydride
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CAS Number | 7580-67-8 |
EC Number | 231-484-3 |
Beilstein Registry Number | 2384789 |
MDL Number | - |
PubChem Substance ID | 62714 |
Merck Number | 14,5533 |
Chemical Name Translation | 氢化锂 |
Wiswesser Line Notation | LI H |
InChI | InChI=1S/Li.H/q+1;-1 |
Canonical SMILES | - |
Signal word |
|
GHS Symbol
WGK Germany | 2 |
Safety Statements | |
- S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
- S27 Take off immediately all contaminated clothing 立即脱掉全部污染的衣服;
- S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
- S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
|
Risk Statements | |
- R34 Causes burns 会导致灼伤
- R25 Toxic if swallowed 吞咽有毒
- R14/15 Reacts violently with water, liberating extremely flammable gases 遇水剧烈反应,释放出高度可燃气体
|
Precautionary statements | |
- P201 Obtain special instructions before use. 使用前获取专门指示。
- P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前,切勿操作。
- P223 Keep away from any possible contact with water, because of violent reaction and possible flash fire. 远离任何与水接触的可能,因为会剧烈反应可能产生闪火。
- P231+P232
- P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
- P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
- P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- P281 Use personal protective equipment as required. 使用所需的个人防护装备。
- P301+P310
- P301+P330+P331
- P303+P361+P353
- P304+P340
- P305+P351+P338
- P307+P311
- P308+P313
- P309+P311
- P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
- P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
- P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
- P330 Rinse mouth. 漱口
- P335+P334
- P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
- P370+P378
- P402+P404
- P403+P233
- P405 Store locked up. 上锁保管。
- P422 Store contents under… 存储目录在…之下。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
|
Hazard statements | |
- H260 In contact with water releases flammable gases which may ignite spontaneously 与水接触时释放可燃气体,可自燃。
- H301 Toxic if swallowed 吞食有毒
- H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
|
Personal Protective Equipment |
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges |
RTECS | OJ6300000 |
Packing Group | I |
UN Number |
1414/2805 |
Storage condition |
20
20℃
Air & Moisture Sensitive
Moisture Sensitive
N/A
No Data Available
water-free area
充氩保存
对湿度敏感 |
Hazard Codes |
F,T
F;T;C |
Hazard Class | 4.3 |
Warnings |
危化品目录(2015) |
TYPE OF TEST : LCLo - Lowest published lethal concentration
ROUTE OF EXPOSURE : Inhalation
SPECIES OBSERVED : Rodent - rat
DOSE/DURATION : 10 mg/m3/4H
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - cough
REFERENCE :
AMIHAB AMA Archives of Industrial Health. (Chicago, IL) V.11-21, 1955-60.
For publisher information, see AEHLAU. Volume(issue)/page/year: 14,468,1956
Restrict |
危险品 |
在有机合成中,用作缩合剂、还原剂、烷基化试剂、克莱逊氏试剂,也可用作干燥剂。
{uni_hamburg} Short: III/24C
{uni_hamburg} Short: II/24A
{uni_hamburg} Short: III/14a
{ALF} A procedure for activation involves treatment with TMS chloride and a catalytic amount of Zn or a Zn salt. This reagent will reduce a ketone to the TMS ether of the alcohol: J. Org. Chem., 59, 217 (1994).
{ALF} Used for preparation of anhydrous Li salts of carboxylic acids prior to reaction with organothium reagents (most often methyl or phenyl) as a useful route to ketones. For a comprehensive review of this method, see: Org. React., 18, 1 (1970). For an example (cyclohexyl methyl ketone), see: Org. Synth. Coll., 5, 775 (1973).
{ALF} For preparation of LiCN by reaction with acetone cyanohydrin, see: Org. Synth. Coll., 7, 517 (1990).
{ALD} Merck: 14,5533