二碳酸二叔丁酯

• 产品号: A14708
• CAS号: 24424-99-5
• 分子式: C10H18O5
• 分子量: 218.24692
• 纯 度: 97+%

产品别名

• 标题: Di-tert-butyl dicarbonate
• IUPAC标准名: di-tert-butyl dicarbonate
• IUPAC传统名: di-tert-butyl dicarbonate
• 别名: Di-tert-butyl pyrocarbonate; BOC anhydride

产品登记号

• MDL号: MFCD00008805
• CAS号: 24424-99-5
• Beilstein号: 1911173
• EC号: 246-240-1

产品性质

• 纯度: 97+%
• 沸点: 56-57°C/0.5mm
• 密度: 0.950
• 闪点: 37°C(99°F)
• 熔点: 21-24°C
• 折射率: 1.4090
• GHS危险声明: H330-H315-H317-H335-H318-H228
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 欧盟危险性物质标志: 易燃性(Flammable) (F)
• GHS警示性声明: P280-P305+P351+P338-P302+P352-P304+P340-P310
• 危险公开号: 11-26-37/38-41-43
• RTECS编号: HT0230000
• 安全公开号: 9-26-28-36/37/39-45-60
• 保存注意事项: Moisture Sensitive
• TSCA收录: 是
• 联合国危险货物等级: 6.1
• 联合国危险货物编号: UN2930
• 联合国危险货物包装类别(PG): I

参考文献

• Carboxylic acids have also been converted to Boc-protected amines, via a one-pot Curtius rearrangement, using the reagent in the presence of sodium azide, with catalytic amounts of TBAB and zinc triflate: Org. Lett., 7, 4107 (2005).
• Reagent for amino group protection as the tert-butyl carbamate (tert-butoxycarbonyl, Boc derivatives), in high yield under mild conditions, widely used in peptide chemistry; see Appendix 6. For practical details, literature references and tabulated results, see: Org. Synth. Coll., 7, 70 (1990). For further examples see: Synthesis, 223 (1987): Org. Synth.Coll., 9, 124, 300 (1998). Benzyl carbamates (Cbz, Z) may be transformed into Boc in a one pot procedure catalyzed by Pd/C: Tetrahedron Lett., 33, 3167 (1992).
• Rapid and efficient formation of Boc derivatives of amines, catayzed by Copper(II) tetrafluoroborate hexahydrate, 26127 has been described: Tetrahdron Lett., 47, 1087 (2006).
• For Boc protection of phenols, alcohols, thiols etc. under phase-transfer conditions, see: Can. J. Chem., 63, 153 (1985).
• Amides can be protected in the presence of a catalytic quantity of DMAP (4-(Dimethylamino)pyridine, A13016): J. Org. Chem., 48, 2424 (1983); Acta Chem. Scand. B, 40, 745 (1986); the amide link of the product undergoes facile alkaline hydrolysis or methanolysis. The nitrogen function of indoles and pyrroles can also be protected under similar conditions: J. Chem. Soc., Chem. Commun., 1699 (1984); Org. Synth.Coll., 9, 121 (1998). 1-Boc indoles may be synthesized from N-Boc 2-alkylanilines: Synthesis, 871 (1991).
• The Boc group is readily cleaved with acid, most often Trifluoroacetic acid, L06374.
• In the presence of 1 equivalent of DMAP in acetonitrile, arylamines are converted to isocyanates, generally in high yield; the dicarbonate here behaves as a convenient phosgene replacement: Angew. Chem. Int. Ed., 34, 2497 (1995). The same reagent system has also been applied to nitroalkanes for the ambient temperature generation of nitrile oxides which were trapped in situ with dipolarophiles: Synthesis, 309 (1997). Carboxylic acids can be esterified in the presence of a catalytic amount of DMAP: Synlett, 263 (2004).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 1995 (2001).