硼氢化钠

• 产品号: 13432
• CAS号: 16940-66-2
• 分子式: BNa
• 分子量: 33.80077
• 纯 度: 98%

产品别名

• 标题: Sodium borohydride
• IUPAC标准名: sodium boranuide
• IUPAC传统名: sodium boranuide
• 别名: Sodium tetrahydridoborate

产品登记号

• MDL号: MFCD00003518
• 默克索引号: 148592
• EC号: 241-004-4
• CAS号: 16940-66-2

产品性质

• 纯度: 98%
• 外观: Powder
• 密度: 1.074
• 熔点: 400°C dec.
• GHS危险声明: H301-H311-H331-H314-H318-H261
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 欧盟危险性物质标志: 易燃性(Flammable) (F)
• GHS警示性声明: P280-P303+P361+P353-P305+P351+P338-P310-P370+P378I-P402+P404
• 危险公开号: 15-23/24/25-34
• RTECS编号: ED3325000
• 安全公开号: 7/8-26-36/37/39-43-45
• 保存注意事项: Moisture Sensitive
• TSCA收录: 是
• 联合国危险货物等级: 4.3
• 联合国危险货物编号: UN1426
• 联合国危险货物包装类别(PG): I

参考文献

• 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).
• Hydroboration of olefins has also been reported under similar conditions: Synlett, 997 (2000).
• Acid chlorides are readily reduced to alcohols; controlled reduction at -78^o 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.
• A vast number of modified borohydride reagents have been reported, with the objective either of increasing the reducing power or improving selectivity. Many examples involve combinations with metal salts:
• 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).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 182 (2005).
• Monograph: J. Seyden-Penne, Reductions by the Alumino- and Borohydrides In Organic Synthesis, 2nd ed., Wiley, N.Y. (1997).
• 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 alternative to Raney nickel for desulfurizations: Synth. Commun., 16, 779 (1986); J. Chem. Soc., Chem. Commun., 819 (1990); J. Org. Chem., 57, 1986 (1992); 58, 2407 (1993); phenols and enols have also been deoxygenated: J. Chem. Soc., Perkin 1, 1897 (1992), and aryl nitrile reduced to benzylamines: Synth. Commun, 32, 1265 (2002). For conversion to Zn(BH₄)₂, see Zinc chloride, A16281. InCl₃: radical reducing system - alternative to Bu₃SnH: J. Am. Chem. Soc., 124, 906 (2002) _.
• The combination of borohydride and iodine (in situ borane) reduces acids to alcohols: J. Org. Chem., 56, 5964 (1991); amino acids to amino alcohols: J. Org. Chem., 58, 3568 (1993); and effects reduction of esters, amides and nitriles, as well as hydroboration of alkenes: Tetrahedron, 45, 4623 (1992). See also Boron trifluoride diethyl etherate, A15275, and Sodium triacetoxyborohydride, B22060.