Sodium Cyanoborohydride 氰基硼氢化钠

CAS 25895-60-7 MFCD00003516


SMILES: [BH3-]C#N.[Na+]


Mol. FormulaCH3BNNa
Mol. Weight63
Melting Point>242
Density1.083 g/mL at 25 °C
SolubilitySoluble in water, THF, methanol
Flash Point-1 °F
Appearance 白色或微黄色固体粉末,是一种温和的还原剂,它广泛用于醛、酮的还原,特别是酮的还原胺化作用。熔点242-243℃
Boiling Point307°C


Chemical NameSodium Cyanoborohydride
CAS Number25895-60-7
Synonym Sodium cyanotrihydridoborate Sodium borocyanohydride Sodium Cyanotrihydroborate(1-) Sodium cyanotrihydroborate 氰基硼氢化钠
MDL NumberMFCD00003516
Beilstein Registry Number4152656
PubChem Substance ID87575903
EC Number247-317-2
Merck Number8606
Chemical Name Translation氰基硼氢化钠
LabNetwork Molecule IDLN01305334
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  • {SA} Additional Reagents for Reductive Amination, Borohydrides, Chemical Synthesis, Glycan Labeling, Glycan Labeling and Analysis, Glycobiology, Post-Translational Modification, Proteomics, Reduction, Synthetic Reagents
  • {SNA} Borohydrides, Chemical Synthesis, Reduction,


  • 有机合成用还原剂,醛、酮、肟、烯胺类还原,β-内酰胺还原成β-氨基酸。氨的甲基化。


  • Tosylhydrazones are reduced to methylenes. The relatively slow reduction of carbonyl compounds enables the tosylhydrazone to be generated in situ: J. Am. Chem. Soc., 93, 1793 (1971); 95, 3662 (1973). For a detailed study of the mechanism of tosylhydrazone reduction, see: J. Org. Chem., 54, 4175 (1989).
  • Unlike borohydride reduction of carbonyl compounds which proceeds readily at the natural pH of the solution, reduction by sodium cyanoborohydride is very slow unless the pH is reduced to 3-4. Selective reduction of iminium ions occurs, however, at pH 6-8, leading to the widespread application of the reagent in reductive aminations of carbonyl compounds: J. Am. Chem. Soc., 93, 2897 (1971); Org. Synth. Coll., 6, 499 (1988). For improved methods using combinations with Ti(IV) chloride or isopropoxide, see: Tetrahedron Lett., 31, 5547 (1990); J. Org. Chem., 55, 2552 (1990).
  • Oximes are reduced to hydroxylamines, as are O-alkyloximes: Tetrahedron Lett., 2493 (1974). Reduction in the presence of TiCl3 gives primary amines, via the imine: Synth. Commun., 18, 777 (1988).
  • Monograph: J. Seyden-Penne, Reductions by the Alumino- and Borohydrides In Organic Synthesis, 2nd ed., Wiley, N.Y. (1997).
  • For reviews of the chemistry of sodium cyanoborohydride, see: Synthesis, 135 (1975); Org. Prep. Proced. Int., 11, 201 (1979).


GHS Symbol
WGK Germany2
Precautionary statements
  • 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。
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
  • 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。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • 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。
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P301+P310+P330
  • P301+P330+P331+P310
  • P303+P361+P353
  • P303+P361+P353+P310+P363
  • P304+P340+P310
  • P305+P351+P338
  • P305+P351+P338+P310
  • P335+P334
  • P370+P378
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P402+P404
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H228 Flammable solid 易燃固体
  • 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。
  • H300 Fatal if swallowed 吞食致命
  • H300+H310+H330
  • H301 Toxic if swallowed 吞食有毒
  • H301+H311+H331
  • H310 Fatal in contact with skin 皮肤接触致命
  • H311 Toxic in contact with skin 皮肤接触中毒
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H330 Fatal if inhaled 吸入致命
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H351 Suspected of causing cancer 怀疑致癌
  • H400 Verytoxictoaquaticlife 对水生生物毒性非常大。
  • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
  • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。
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
Signal word
Safety Statements
  • 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;
  • 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;
  • S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后,立即用大量…(由生产厂家指定)冲洗;
  • 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);
  • 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;
  • S8 Keep container dry 保持容器干燥;
  • S1 Keep locked up 上锁;
  • 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”
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
  • S50 Do not mix with ... (to be specified by the manufacturer) 不要与……(由生产厂家指定)混合;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
Packing GroupII
UN Number 3134
Risk Statements
Storage condition Moisture Sensitive Store under Argon 储存温度2-8°C,充氩储存 0-10°C 储存温度2-8°C ,充氩保护。 0-10
Hazard Codes F,T+,N F,T,N T+,N
Hazard Class4.3/6.1


  • 用途一:是一种温和的还原剂,它广泛用于醛、酮的还原,特别是酮的还原胺化作用。
  • Sigma Aldrich:25895-60-7(sigmaaldrich)
  • TCI Shanghai:氰基硼氢化钠[还原剂] Sodium Cyanoborohydride [Reducing Agent],>;95.0%(T)(25895-60-7)
  • Acros Organics:Sodium cyanoborohydride, 1M solution in THF, AcroSeal?(25895-60-7)
  • 氰基硼氢化钠价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 XW258956071 氰基硼氢化钠;氰基三氢化硼钠 10g 135元 2011/08/23 XW258956072 氰基硼氢化钠;氰基三氢化硼钠 50g 498元 2011/08/23 XW258956073 氰基硼氢化钠;氰基三氢化硼钠 250g 1996元
  • 用途二:有机合成用还原剂,醛、酮、肟、烯胺类还原,β-内酰胺还原成β-氨基酸。氨的甲基化。
  • 存储注意事项:氮气保护;湿度敏感
  • 海关编码:28500020
  • 敏感性:Moisture Sensitive
  • Alfa Aesar:Sodium cyanoborohydride, 95%(25895-60-7)
  • Hazard Note:Toxic/Highly Flammable
  • MSDS 信息:Sodium cyanoborohydride(25895-60-7).msds
  • 下游产品:N-甲基-P-氨基苯甲醚 --> 依那普利 --> N-异丙基-2-(哌嗪-1-基)吡啶-3-胺 --> 6-羧基二氢吲哚 --> 4-氨基嘧啶 --> 2-氨基环己腈 --> 二氢吲哚-6-甲酸乙酯 --> 3-(二甲基氨基)苯硼酸 --> 4-N-叔丁氧羰基-4-N-甲基氨基哌啶 --> 赖诺普利 --> 1-(环丙甲基)哌嗪 --> 1-叔丁氧羰基-4-甲氨基哌啶 --> N-Boc-4-(环丙甲基)哌嗪 --> 4-肼基哌啶-1-羧酸叔丁酯 --> 1-胡椒基哌嗪 --> 6-溴-3,4-二氢-3-硝基-2H-苯并吡喃 --> 1-(3-吡咯烷丙基)哌嗪 --> 4-吡咯烷-1-基-哌啶 --> 4-二甲氨基哌啶 --> 奈替米星
  • MOL 文件:25895-60-7.mol
  • F:10-21
  • 有吸湿性。水中溶解度: 2120 g/L水29°C )(慢慢分解) ,溶于甲醇,溶于THF(372 g/L at 28°C, 410 g/L at 46°C, 422 g/L at 62°C),溶于二甘醇二甲醚(176 g/L at 25°C),微溶于乙醇,不溶于醚、苯和己烷。在pH3的酸性溶液中稳定,在12N盐酸中能快速水解。