sodium cyanoboranuide

• ChemBase编号: 88866
• 分子式: CH2BNNa
• 平均质量: 61.83405
• 单一同位素质量: 62.01779875
• SMILES: [BH2-]C#N.[Na+]
• Canonical SMILES: [BH2-]C#N.[Na+]
• InChI: InChI=1S/CH3BN.Na/c2-1-3;/h2H3;/q-1;+1
• InChIKey: CVDUGUOQTVTBJH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: sodium cyanoboranuide
• IUPAC传统名: sodium cyanoboranuide
• 别名: 氰基硼氢化钠; 氰基硼氢化钠; 氰基硼氢化钠 溶液; Sodium cyanoborohydride; Sodium cyanotrihydroborate; Sodium cyanoborohydride; Sodium borocyanohydride; Sodium cyanotrihydroborate; Sodium cyanoborohydride solution; Sodium cyanotrihydridoborate; SODIUM CYANOBOROHYDRIDE; Sodium (T-4)-(Cyano-C)trihydroborate(1-); Sodium Cyanotrihydroborate(1-)

登记号

• CAS号: 25895-60-7
• EC号: 247-317-2
• MDL号: MFCD00003516
• Beilstein号: 4152656
• 默克索引号: 148606
• PubChem SID: 24857889; 162075764; 24857879; 24849595
• PubChem CID: 20587905
• 维基百科标题: Sodium_cyanoborohydride

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): -1.5879
• LogD (pH = 7.4): -1.5879
• Log P: -1.5879
• 摩尔折射率: 9.0556 cm^3
• 极化性: 4.7723866 Å^3
• 极化表面积: 23.79 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO (Sparingly); H2O: soluble, clear to slightly hazy; Methanol; soluble in water; Soluble in water, THF, methanol
• 外观: Powder; White Solid; white to off-white powder, hygroscopic
• 熔点: >242 °C (dec.)(lit.); >242°C; >242(dec.)°C; >300°C; >300°C dec.; 241 °C decomp.
• 闪点: 1.4 °F; -17 °C
• 密度: 0.915 g/mL at 25 °C; 1.083 g/mL at 25 °C; 1.20; 1.20 g/cm^3

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• 保存注意事项: Highly Flammable/Very Toxic/Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 环境危害性(Nature polluting) (N); 有毒(Toxic) (T); 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 1992; 2922; 3179; UN3134
• 德国WGK号: 3
• 联合国危险货物等级: 3; 4.1; 4.3; 6.1; 8
• 联合国危险货物包装类别(PG): 2; II
• 澳大利亚Hazchem: 2X
• 危险公开号: 11-15-26/27/28-32-34-50/53; 11-19-23/24/25-32-36/37/38-50/53; 26/27/28-32-34-50/53; R:10-25
• 安全公开号: 16-26-36/37-45-61; 26-28-36/37/39-43-45-61; 26-28-36/37/39-45-60-61; 26-28-36/37/39-45-61; S:16-28-29-36/37/39-45
• 欧盟危险货物分类: FT2
• 欧盟危险识别号(EUHIN): 4.1B
• 美国ERG指导号: 134
• TSCA收录: 是
• 欧盟危险品索引: not listed
• GHS危险品标识: GHS02; GHS05; GHS06; GHS09
• GHS警示词: Danger
• NFPA704:
  

  2

  3

  2

  W
• GHS危险声明: H225-H301-H311-H314-H330-H335-H400-H411; H228-H260-H300-H310-H314-H330-H410; H228-H261-H300-H310-H330-H314-H318-H400-H410; H300-H310-H314-H330-H410
• GHS警示性声明: P210-P223-P231 + P232-P260-P370 + P378-P422; P210-P260-P273-P280-P284-P301 + P310; P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A; P260-P264-P273-P280-P284-P301 + P310
• 个人保护装置: 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
• RID/ADR: UN 1992 3/PG 2; UN 2922 8/PG 2; UN 3179 4.1/PG 2
• 欧盟补充危害声明: Contact with acids liberates very toxic gas.; Contact with acids liberates very toxic gas., May form explosive peroxides.

产品相关信息

• 纯度: ≥95%; ≥95.0% (RT); 90%; 95%
• 浓度: 1.0 M in THF; 5.0 M in 1 M NaOH
• 级别: purum; reagent grade
• 线性分子式: NaBH3CN

详细说明

MP Biomedicals - 02199862

Aqueous solutions may be slightly hazy.

MP Biomedicals - 02156628

Purity: 90% Aqueous solutions may be slightly hazy.

Sigma Aldrich - 296945

包装
50, 500 mL in poly bottle
Application
Reactant for:
• Direct conversion of heterocyclic aldehydes to esters (oxidizing behavior)1
• Reductive amination reactions2
• Intramolecular reductive cyclization reactions3
• Reductions reactions4
• Preparation of dicyanoborate-based ionic liquids as hypergolic fluids for bipropellants5

Sigma Aldrich - 296813

包装
100, 800 mL in Sure/Seal™
Application
Reactant for:
• Direct conversion of heterocyclic aldehydes to esters (oxidizing behavior)1
• Reductive amination reactions2
• Intramolecular reductive cyclization reactions3
• Reductions reactions4
• Preparation of dicyanoborate-based ionic liquids as hypergolic fluids for bipropellants5

Sigma Aldrich - 71435

Other Notes
综述1,2；使用 NaCNBH4 选择性还原，使用氯化锌改性3；使用碘化锌?4

Sigma Aldrich - 156159

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
用于选择性还原反应的试剂。
用于醛1、酮还原性胺化2以及胺还原性烷化的试剂。3
Features and Benefits
用于合成新型酚氧桥联二镧(III) 络合物，该络合物具有金属蛋白模型以及基础化学和应用化学方面的应用前景。4
包装
1 kg in poly bottle
10 kg in steel drum
10, 25, 50, 250 g in poly bottle

Toronto Research Chemicals - S615500

Sodium Cyanoborohydride is a commonly used as a reagent in the reductive amination of aldehydes and ketones and in the reductive alkylation of amines.

参考文献

• 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).
• Monograph: J. Seyden-Penne, Reductions by the Alumino- and Borohydrides In Organic Synthesis, 2nd ed., Wiley, N.Y. (1997).
• 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).
• 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).
• For reviews of the chemistry of sodium cyanoborohydride, see: Synthesis, 135 (1975); Org. Prep. Proced. Int., 11, 201 (1979).