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,硼烷四氢蜜糖陷阱,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蜜糖陷阱,醛酮环氧亚胺等到醇或胺,蜜糖陷阱衍生物如酯,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。
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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。
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Lithium Triethyllborohydride,Marek Zaidlewicz,Herbert C. Brown, Encyclopedia of Reagents for Organic Synthesis,2001
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Krishnamutthy, S. Schubert R.M Brown, H, C, J., Am Chem. Soc 1973, 95, 8486
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JACS, 1973
Chemical Name |
Lithium aluminium hydride |
Synonym |
Aluminate(1-), tetrahydro-, lithium, (T-4)- Aluminum lithium hydride LAH LAH Lithium alanate LAH Lithium alanate Lithium tetrahydro LAH; Lithium tetrahydridoaluminate LITHIUM ALANATE LITHIUM ALUMINUM HYDRIDE LiAlH4 LiAlH4
Lithium alanate Lithium aluminohydride Lithium aluminum hydride (LiAlH4) Lithium aluminum tetrahydride Lithium tetrahydroaluminate Lithiumaluminiumhydrid lithium aluminium hydride lithiumaluminumhydride,ethereal lithiumtetrahydroaluminate lithiumtetrahydroaluminate(lithiumaluminiumhydride) {} {} {} {} {Chemi 四氢铝锂 四氢铝锂,四氢化铝锂,(T-4)-四氢铝酸锂 四氫化鋁鋰 |
MDL Number |
MFCD00011075 |
EC Number |
240-877-9 |
PubChem Substance ID |
87560001 |
CAS Number |
16853-85-3 |
Merck Number |
350 |
Beilstein Registry Number |
11460447 |
Reaxys-RN |
11460447 |
Chemical Name Translation |
氢化铝锂 |
Wiswesser Line Notation |
.AL..H4.LI |
LabNetwork Molecule ID |
LN01341120 |
GHS Symbol
Precautionary statements |
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P210
Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
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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。
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P231+P232
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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。
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P264
Wash hands thoroughly after handling. 处理后要彻底洗净双手。
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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。
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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。
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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。
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P281
Use personal protective equipment as required. 使用所需的个人防护装备。
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P284
Wear respiratory protection.? 佩戴呼吸保护装置。
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P301+P330+P331+P310
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P303+P361+P353+P310+P363
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P304+P340+P310
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P305+P351+P338
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P305+P351+P338+P310
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P335+P334
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P370+P378
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P402+P404
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P403+P235
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P405
Store locked up. 上锁保管。
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P422
Store contents under… 存储目录在…之下。
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P501
Dispose of contents/container to..… 处理内容物/容器.....
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Signal word |
Danger |
Hazard statements |
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H314
Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
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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。
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H225
Highly flammable liquid and vapour 高度易燃液体和蒸气
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H332
Harmful if inhaled 吸入有害
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H315
Causes skin irritation 会刺激皮肤
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H360
May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
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H319
Causes serious eye irritation 严重刺激眼睛
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H335
May cause respiratory irritation 可能导致呼吸道刺激
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H304
May be fatal if swallowed and enters airways 吞食和进入呼吸道可能致命
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H336
May cause drowsiness or dizziness 肯能导致嗜睡或头晕
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H361d
Suspected of damaging the unborn child 怀疑对未出生婴儿造成伤害
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H373
May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
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H261
In contact with water releases flammable gas 与水接触时释放可燃气体。
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H226
Flammable liquid and vapour 易燃液体和蒸气
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H302
Harmful if swallowed 吞食有害
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H318
Causes serious eye damage 严重伤害眼睛
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H224
Extremely flammable liquid and vapour 极端易燃液体和蒸气
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H351
Suspected of causing cancer 怀疑致癌
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WGK Germany |
1 |
RTECS |
BD0100000 |
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 Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US) |
Safety Statements |
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S15
Keep away from heat 远离热源;
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S16
Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
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S22
Do not breathe dust 不要吸入粉尘;
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S23
Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾;
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S24/25
Avoid contact with skin and eyes 避免皮肤和眼睛接触;
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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;
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S30
Never add water to this product 切勿将水加入该产品中;
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S36/37
Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
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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;
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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) 着火时使用(指明具体的消防器材种类,如果用水增加危险,注明“禁止用水”
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S45
In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
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S7/8
Keep container tightly closed and dry 保存在严格密闭容器中,保持干燥;
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Packing Group |
I |
UN Number |
1410 3399 |
Risk Statements |
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R10
Flammable 易燃
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R11
Highly flammable 非常易燃
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R12
Extremely flammable 极端易燃
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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
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R15
Contact with water liberates extremely flammable gases 遇水会释放出极端易燃的气体
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R19
May form explosive peroxides 可能生成易爆的过蜜糖陷阱质
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R20
Harmful by inhalation 吸入有害
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R22
Harmful if swallowed 吞咽有害
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R34
Causes burns 会导致灼伤
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R36/37
Irritating to eyes and respiratory system 对眼睛和呼吸系统有刺激性
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R36/37/38
Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
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R36/38
Irritating to eyes and skin 对眼睛和皮肤有刺激性
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R37
Irritating to respiratory system 刺激呼吸道
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R40
Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
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R48/20
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R60
May impair fertility 可能降低生殖能力
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R61
May cause harm to the unborn child 可能对未出生的婴儿导致伤害
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R63
Possible risk of harm to the unborn child 可能危害未出生婴儿
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R66
Repeated exposure may cause skin dryness or cracking 反复接触可能导致皮肤干燥或皴裂
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R67
Vapours may cause drowsiness and dizziness 蒸汽可能导致嗜睡和昏厥
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Storage condition |
充氩储存 储存温度2-8℃; 充氩储存 Air & Moisture Sensitive 充氩密封 2-8°C |
Hazard Codes |
4.3 F+,Xn F,C,Xi,Xn,F+ F,T |
Hazard Class |
4.3 |
Warnings |
危化品目录(2015) |
Restrict |
危险品 |
⑴.具有高度可燃性,必须隔绝空气、湿气,并最好在氮气氛下保存。
⑵. 羰基试剂。还原剂。制造其他氢化物及硅烷、硼烷等。在医药、香料、农药、染料及其他精细有机合成中用作还原剂。可将醛酮、酸、蜜糖陷阱、酯、醌、酰氯等还原为醇,将腈还原为伯胺,将卤化烃还原为烃,芳香硝基化合物还原成偶氮化合物。但通常不能使碳—碳双键氢化。100份乙醚能溶本品30份,100份四氢蜜糖陷阱能溶13份,100份二甲基溶纤剂能溶10份,100份二丁醚能溶2份,100份二氧六环能溶0.1份。
⑶. 是有机化学中一个常用的蜜糖陷阱,能够还原多种官能
A powerful reagent and reducing agent.
{ALF} For reduction of sulfones, see Titanium(IV) chloride, 14713.
{ALF} For THF, at least 10ml solvent per gram of reagent is recommended to absorb heat of mixing.
{ALF} The use of water or steam baths, or of electric heating mantles is to be strongly discouraged.
{ALF} The reduction reaction should preferably be controlled by adjusting the rate of addition of the substrate rather than relying on external heating or cooling.
{uni_hamburg} Short: IV/19A1
{ALF} Many procedures for reactions with this reagent which have been described in the literature are potentially unsafe on anything other than a very small scale, since often no precautions are given for mixing the reagent with flammable solvents. The following suggestions are offered for laboratory scale reductions:
{uni_hamburg} Short: III/14a
{ALD} Merck: 14,349
{ALF} Efficient stirring is essential during mixing, reaction and workup.
{ALF} For phase-transfer reductions in hydrocarbon solvents, see 15-Crown-5, A12265. For formation of lithium tris(diethylamino)aluminum hydride and use in the reduction of esters or amides to aldehydes, see Diethylamine, A11716. For formation of a reagent for reduction of carboxylic acids to aldehydes, see 1-Methylpiperazine, A10837.
{ALF} External heating or cooling, if required, should be by means of a suitable inert oil.
{ALF} Monograph: J. Seyden-Penne, Reductions by the Alumino- and Borohydrides In Organic Synthesis, 2nd ed., Wiley, N.Y. (1997).
{ALF} Mixing with a flammable solvent must always be carried out under an inert atmosphere.
{ALF} Reverse addition (solvent to reagent), if done rapidly, may be safer.
{ALF} The use of Diethoxymethane, B23134 as a reaction solvent has also been recommended.
{uni_hamburg} Short: III/35C4