Sodium borohydride 硼氢化钠
CAS 16940-66-2 MFCD00003518
化学结构图
SMILES: [BH4-].[Na+]
化学属性
| Mol. Formula | NaBH4 |
|---|---|
| Mol. Weight | 37.83 |
| Melting Point | >;300 °C (dec.)(lit.) |
| Density | 0.998 g/mL at 25 °C |
| TSCA | Yes |
| Solubility | Soluble in water, ammonia and amines. Insoluble in ether |
| Boiling Point | 130°C |
| Flash Point | 69 ºC |
| Stability | 对湿度敏感 |
| Appearance | tablets |
| Danger-Level | - |
| pH | -:- |
| Redox | - |
别名和识别编码
| Chemical Name | 硼氢化钠 |
|---|---|
| Synonym | VenPure® 四氢硼酸钠 Natriumborhydrid 四氢硼酸(1-)钠 Sodium tetrahydroborate sodiumborohydrate Sodium tetrahydridoborate Natriumtetrahydridoborat Sodium borohydrate 硼氢钠 COBALT-DOPED SODIUM BOROHYDRIDE SODIUM TETRAHYDROBORATE Sodium borohydride 硼氢化钠, 98% MIN VenPure® AF 四氢硼酸钠 BH4Na AF 硼氢化钠, 97+% hidkitexdf Natriumborhydrid auf aluminiumoxid Borate(1-), tetrahydro-, sodium borohydruredesodium(french) Sodium hydroborate BH4Na 四氢硼酸钠 钴掺杂的硼氢化钠 Borohydrure de sodium 四氢硼酸钠 硼氢化钠 氧化铝负载硼氢化钠 SBH 四氢硼酸钠 Borol SODIUM TETRAHYDRIDOBORATE 四氢硼钠 Sodium borohydride (Na(BH4)) NaBH4 Natriumborhydrid (Feingranulat) Sodium borohydride (NaBH4) NaBH4 borol SODIUM BOROHYDRIDE SODIUM BORANATE 硼氢化钠 四氢硼化钠 SODIUM TETRAHYDRIDEBORATE Sodium tetrahydroborate(1-) Borate(1-)tetrahydro-,sodium Natriumboranat borohydruredesodium Borate(1-),tetrahydro-,sodium 硼氢钠,四氢硼钠,钠硼氢,氢硼化钠,四氢硼酸钠 硼氢化钠, STABLE AQ. SOLN., 4.4M IN 14M NAOH Hidkitex DF 硼氢化钠 溶液 氢硼化钠 |
| CAS Number | 16940-66-2 |
| PubChem Substance ID | 24868735 |
| EC Number | 241-004-4 |
| MDL Number | MFCD00003518 |
| Merck Number | 14,8592 |
| Beilstein Registry Number | 2384789 |
| Chemical Name Translation | 硼氢化钠 |
| Wiswesser Line Notation | NA B-H4 |
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分类
- {SNA} Analytical Reagents,
- {SNA} Alkaline β-elimination, Borohydrides, Chemical Deglycosylation, Chemical Synthesis, Deglycosylation Strategies, Essential Chemicals, Glycobiology, Inorganic Salts, Solutions and Reagents, Molecular Biology, Post-Translational Modification, Proteomics, Reagent Plus, Reduction, Research Essentials, Synthetic Reagents
- {SNA} Analytical Reagents, Analytical/Chromatography, Applications, Atomic Absorption Spectroscopy (AAS), Food & Beverage Analysis, Matrix Modifiers, Buffers and Reducing Reagents for AA
- {SNA} Borohydrides, Chemical Synthesis, Reduction, Synthetic Reagents
产品应用
- 硼氢化钠是一种良好的还原剂，它的特点是性能稳定，还原时有选择性。可用作醛类、酮类和酰氯类的还原剂，塑料的发泡剂，制造双氢链霉素的氢化剂，制硼氢化钾的中间体，合成硼烷的原料，以及用于造纸工业含汞污水的处理剂。用作制造乙硼烷和其他高能燃料的原料，也用于医药工业等。
相关文献及参考
- Acid chlorides are readily reduced to alcohols; controlled reduction at -78o to give the aldehyde has been reported; see, e.g.: Synth. Commun., 12, 839 (1982). See also Bis(triphenylphosphine)copper(I) borohydride, A13730. For an indirect method of reduction, see Triethyl phosphite, L00339.
- For a brief feature on uses of the reagent in synthesis, see: Synlett, 182 (
- LiCl: reduction of amino acids via Me esters: Tetrahedron Lett., 39, 917 (1998). CaCl2: selective 1,2-reduction enones: Chem. Lett., 1847 (1991). CeCl3: increased selectivity for 1,2-reduction of enones: J. Chem. Soc., Chem. Commun., 601 (1978); reduction of ketones in the presence of aldehydes: J. Am. Chem. Soc., 101, 5848 (1979). CuCl: dehalogenation of aryl iodides and bromides: J. Org. Chem., 54, 5308 (1989); reduction of nitro compounds: Chem. Ind. (London), 75 (1984). CuSO4: reduction of esters, alkenes, nitriles and nitro compounds; amides and acids inert: Synlett, 419 (1990) [but see also Synlett, 79 (1993): Cu(OAc)2 preferred for reduction of nitro-groups]; reduction of azides: Synth. Commun., 24, 549 (1994). NiCl2: generation in situ of nickel boride, as an alternativ
- Merck: 14,8592
- Reductive alkylation of amines can be effected with NaBH4/formaldehyde; see e.g.: Synthesis, 743 (1980); or TFA: Synthesis, 709 (1987). See also Sodium cyanoborohydride, 87839. Reductive alkylation of aromatic amines with a variety of aldehydes and ketones has been reported, using NaBH4/H2SO4: Synthesis, 121 (1993).
- The reduction of aldehydes and ketones to alcohols occurs in alcoholic or aqueous media. For highly selective reduction of aldehydes in the presence of ketones, see: Synth. Commun., 18, 1927 (1988). For enantioselective reduction, see L-tert-Leucine, L13707. Borohydride reductions can be carried out in organic solvents, e.g. toluene, under phase-transfer conditions, amenable to scale-up: Org. Process Res. Dev., 1, 287 (1997).
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安全信息
GHS Symbol
- H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
- 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
- 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
- H302 Harmful if swallowed 吞食有害
- H312 Harmful in contact with skin 皮肤接触有害
- H311 Toxic in contact with skin 皮肤接触中毒
- H261 In contact with water releases flammable gas 与水接触时释放可燃气体。
- H301+H311
- H315 Causes skin irritation 会刺激皮肤
- H319 Causes serious eye irritation 严重刺激眼睛
- H317 May cause an allergic skin reaction 可能导致皮肤过敏
- H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled 吸入可能导致过敏或哮喘症状或呼吸困难
- H350 May cause cancer 可能致癌
- H341 Suspected of causing genetic defects 怀疑导致遗传性缺陷
- H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
- P402+P404
- P308+P313
- P231+P232
- 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。
- P370+P378
- P201 Obtain special instructions before use. 使用前获取专门指示。
- P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P305+P351+P338
- P304+P340+P310
- P301+P312+P330
- P303+P361+P353
- 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。
- P422 Store contents under… 存储目录在…之下。
- P301+P310
- P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
- 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）；
- 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；
- 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；
- S7/8 Keep container tightly closed and dry 保存在严格密闭容器中，保持干燥；
- 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”
- S35 This material and its container must be disposed of in a safe way 该物料及其容器必须以安全方式处置；
- S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
- S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
- S22 Do not breathe dust 不要吸入粉尘；
- S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中，参考特别指示/安全收据说明书；
- S27 Take off immediately all contaminated clothing 立即脱掉全部污染的衣服；
- S20 When using do not eat or drink 使用时，不得进食，饮水；
- S33 Take precautionary measures against static discharges 对静电采取预防措施；
- S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
- S4 Keep away from living quarters 远离生活区；
- S9 Keep container in a well-ventilated place 保持容器在通风良好的场所；
- S50 Do not mix with ... (to be specified by the manufacturer) 不要与……（由生产厂家指定）混合；
- 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；
- R19 May form explosive peroxides 可能生成易爆的过氧化物质
- R21/22 Harmful in contact with skin and if swallowed 皮肤接触和不慎吞咽有害
- R15 Contact with water liberates extremely flammable gases 遇水会释放出极端易燃的气体
- R34 Causes burns 会导致灼伤
- R60 May impair fertility 可能降低生殖能力
- R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
- R24/25 Toxic in contact with skin and if swallowed 皮肤接触及吞食都有毒
- R62 Possible risk of impaired fertility 有削弱生殖能力的危险
- R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入，皮肤接触及吞食都有毒
- R42/43
- R63 Possible risk of harm to the unborn child 可能危害未出生婴儿
- R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
- R51/53
- R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
- R35 Causes severe burns 会导致严重灼伤
- R49 May cause cancer by inhalation 吸入会致癌
- R68 Possible risk of irreversible effects 可能有不可挽回的作用的危险
- R50/53
- R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
- R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 18 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : AMIHAB AMA Archives of Industrial Health. (Chicago, IL) V.11-21, 1955-60. For publisher information, see AEHLAU. Volume(issue)/page/year: 17,124,1958
TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 18 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 14KTAK "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964 Volume(issue)/page/year: -,693,1964
TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 160 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 14KTAK "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964 Volume(issue)/page/year: -,693,1964
TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 60 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 14KTAK "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964 Volume(issue)/page/year: -,693,1964
其他信息
- 有吸湿性，在潮湿空气中分解，在300℃干燥空气中稳定。缓慢加热至400℃分解，急热则500℃开始分解。溶于水、液氨、胺类，微溶于四氢呋喃，不溶于乙醚、苯、烃。
- 灭火剂:干粉、干砂
- 储运特性:库房
- 用途二:是一种良好的还原剂，它的特点是性能稳定，还原时有选择性。可用作醛类、酮类和酰氯类的还原剂，塑料的发泡剂，制造双氢链霉素的氢化剂，制造硼氢化钾的中间体，合成硼烷的原料，以及用于造纸工业和含汞污水的处理剂等。
- {Chem
- 还原能力:硼氢化钠是比较温和的还原剂,它对醛,酮的还原效里比较好.常用溶剂是醇,四氢呋喃,DMF，水等。他一般不还原酯基，羧基，酰胺，但在高浓度，高温再配合合适溶齐或用路易斯酸催化时，可以还原酯基等比较弱的羰基。 还原醛，酮不仅温和，而且效果很好。基本的操作：使用甲醇或者乙醇为溶剂，醛酮羰基化合物与硼氢化钠的物质量1:1就足够了。温度可以采用阶段升温法，比如开始用50度，当反应足够时间后如1小时，再回流反应，薄层监视进度即可。反应一般是很彻底的。一般讲，溶剂用量只要能够满足反应后不至于形成白色粘浆即可。反应不许要严格无水；甚至有用水当作溶剂的例子：比如还原对甲酰基苯甲酸，还原的是甲酰基（甲醛),先用氢氧化钠中和了羧基，然后在水中反应即可成功还原甲酰基。 硼氢化钠在酸性条件会快速分解释放氢气，所以它不能在酸性条件反应，但可以在碱性条件下使用。硼氢化钠接触羧酸是会快速分解释放氢气。所以它不能单独还原羧酸，必须与碘联合使用，先与羧酸反应至气泡停止后就加入碘，继续放气体。随后加入盐酸分解形成的硼酸酯，就可以获得醇。注意：反应要在无水THF进行，THF必须钠回流至二苯酮变蓝才能使用！否则在羧酸与硼氢化钠反应过程中形成乳状物，而不是澄清液体。 用硼氢化钠与无水氯化锌（200度以上脱水干燥）在无水THF中反应3小时后，制得硼氢化锌。该溶液混合物不需要进行分离纯化，就可以当作硼氢化锌使用，来在THF的回流温度下还原羧酸或者酯，收率不错，但是双键可能会有些受影响，比如还原肉桂酸，会有一部分双键还原的产物。
- 毒性分级:高毒
- 发现历程:硼氢化钠是由 H. C. Brown 和他的老板Schlesinger 于1942年在芝加哥大学发现的。当时的目的是为了研究硼烷和一氧化碳络合物的性质，但却发现了硼烷对有机羰基化合物的还原能力。由于当时硼烷属于稀有物质，因此并没有引起有机化学家的重视。硼烷化学的发展得益于第二次世界大战，当时美国国防部需要寻找一种分子量尽量小的挥发性铀化合物用于裂变材料铀235的富集。硼氢化铀U(BH4)4符合这个要求。该化合物的合成需要用到氢化锂，然而氢化锂的供应很少，于是便宜的氢化钠便被用来作原料，而硼氢化钠就在这个过程中被发现。后来，因为六氟化铀的处理工艺问题得到解决，国防部便放弃了通过硼氢化铀来富集铀235的计划，而Brown 的研究课题就变成了如何方便地制备硼氢化钠。Army Signal Corps公司对这个新化合物的野外就地制备大量氢气的用途产生了兴趣。在他们的资
- 用途:硼氢化钠的氢在这里显-1价故有很强还原性可以还原有一定氧化性的无机物，它主要用于有机合成中的-COOH还原成-CH20H，起到有机合成的很大作用所以被成为“万能还原剂”。是一种良好的还原剂，它的特点是性能稳定，还原时有选择性。可用作醛类，酮类和酰氯类的还原剂，塑料的发泡剂，制造双氢链霉素的氢化剂，制造硼氢化钾的中间体，合成硼烷的原料，以及用于造纸工业和含汞污水的处理剂。 硼氢化钠给有机化学家们提供了一种非常便利温和的还原醛酮类物质的手段。在此之前，通常要用金属/醇的办法来还原羰基化合物，而硼氢化钠可以在非常温和的条件下实现醛酮羰基的还原，生成一级醇、二级醇。还原步骤是先把底物溶于溶剂，一般是甲醇或者乙醇，然后用冰浴冷却，将硼氢化钠粉末加入混合物搅拌至反应完全即可。反应过程可以用薄层层析监测。如果溶剂不是醇，那么需要另加甲醇或者乙醇一同反应。硼氢化钠是一种中等强度的还原剂，所以在反应中表现出良好的化学选择性，只还原活泼的醛酮羰基，而不与酯、酰胺作用。
- MOL 文件:16940-66-2.mol
- 概述:硼氢化钠是一种无机化合物，为白色至灰白色细结晶粉末或块状，在室温下与甲醇迅速反应生成氢气。吸湿性强，容易吸水潮解，沸点500℃(真空);熔点400℃;可溶于水和低级醇、液氨，不溶于乙醚、苯、烃类;相对密度(水=1):1.07,在无机合成和有
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