di-tert-butyl dicarbonate

• ChemBase编号: 85817
• 分子式: C10H18O5
• 平均质量: 218.24692
• 单一同位素质量: 218.11542368
• SMILES: O(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)OC(=O)OC(C)(C)C
• InChI: InChI=1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3
• InChIKey: DYHSDKLCOJIUFX-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: di-tert-butyl dicarbonate
• IUPAC传统名: di-tert-butyl dicarbonate
• 别名: 二叔丁基二碳酸酯; 焦碳酸二叔丁酯; 二碳酸二叔丁酯; 二碳酸二叔丁酯 溶液; Di-tert-butyl pyrocarbonate; Di-tert-butyl dicarbonate; di-tert-butyl pyrocarbonate; Boc₂O; Di-tert-butyl dicarbonate; Di-tert-butyl dicarbonate solution; C,C'-bis(1,1-Dimethylethyl) Ester Dicarbonic Acid; Bis(1,1-dimethylethyl) Ester Dicarbonic Acid; Oxydi-formic Acid Di-tert-butyl Ester; BOC-anhydride; Bis(1,1-dimethylethyl) Dicarbonate; Bis(tert-butyl) Dicarbonate; Di-tert-butyl Dicarbonate; Di-tert-butyl Oxydiformate; Pyrocarbonic Acid Di-tert-butyl Ester; tert-Butoxycarbonyl Anhydride; tert-Butyl Dicarbonate; tert-Butyl Dicarbonate; Bis(tert-butyl) pyrocarbonate; BOC anhydride; Bis(tert-butyl) dicarbonate 97+%; Di-t-butyl pyrocarbonate; DI-t-BUTYL DICARBONATE

登记号

• CAS号: 24424-99-5
• EC号: 246-240-1
• MDL号: MFCD00008805
• Beilstein号: 1911173
• PubChem SID: 24862282; 24852315; 162072933; 24867291; 24861420
• PubChem CID: 90495
• CHEBI ID: 48500
• Chemspider ID: 81704
• 维基百科标题: Di-tert-butyl_dicarbonate

理论计算性质

• 极化表面积: 61.83 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 3.033982
• LogD (pH = 7.4): 3.033982
• Log P: 3.033982
• 摩尔折射率: 52.9404 cm^3
• 极化性: 21.461906 Å^3

分子性质

理化性质

• 溶解度: Chloroform; Ethyl Acetate; insol in water; most organic solvents
• 外观: colourless solid; Pale Yellow Solid
• 熔点: 21-24°C; 22–24 °C; 22-26 °C; 23 °C(lit.); 23°C
• 沸点: 56-57 °C/0.5 mmHg(lit.); 56-57°C; 56-57°C/0.5mm; 56–57 °C (0.5 mmHg); 56-57°C/0.5mm; 65-67 °C
• 闪点: -1 °C; 1.4 °F; 107 °C; -15 °C; -17 °C; 224.6 °F; 30.2 °F; 37 °C; 37°C; 37°C(99°F); 5 °F; 98.6 °F
• 密度: 0.913 g/mL at 25 °C; 0.934 g/mL at 25 °C; 0.95; 0.95 g/mL at 25 °C(lit.); 0.95 g·cm^−3; 0.950; 0.950 g/ml; 0.951 g/mL at 25 °C; 1.162 g/mL at 25 °C
• 折射率: 1.4090; n20/D 1.389; n20/D 1.408; n20/D 1.409(lit.)

安全信息

• 保存条件: 0°C; Refrigerator
• 保存注意事项: Moisture Sensitive; Very Toxic/Flammable/Irritant/Corrosive/Moisture Sensitive/Air Sensitive/Keep Cold/Store under Argon
• RTECS编号: HT0230000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 剧毒(Highly toxic) (T+); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 1992; 1993; 2810; 2929; UN2930
• 德国WGK号: 3
• 联合国危险货物等级: 3; 6.1
• 联合国危险货物包装类别(PG): 1; 2; I; III
• 澳大利亚Hazchem: 3Y
• 危险公开号: 10-26-36/37/38-43; 11-19-26-36/37/38-43; 11-26-36/37/38-43; 11-26-37/38-41-43; 26-36/37/38-40-43; R:10-36/37/38
• 安全公开号: 16-26-28-36/37-45; 26-28-36/37-45; 7/9-16-26-28-36/37-45; 9-26-28-36/37/39-45-60; S:16-20-25-26-37/39
• 欧盟危险货物分类: F1
• 欧盟危险识别号(EUHIN): 3B
• 美国ERG指导号: 128
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS05; GHS06; GHS08
• GHS警示词: Danger
• 主要危害: toxic on inhalation T+
• GHS危险声明: H225-H315-H319-H330-H335; H225-H315-H319-H330-H335-H336; H226-H315-H317-H319-H330-H335; H315-H319-H330-H335-H351; H330-H315-H317-H335-H318-H228
• GHS警示性声明: P210-P260-P284-P305 + P351 + P338-P310; P260-P280-P284-P305 + P351 + P338-P310; P260-P281-P284-P305 + P351 + P338-P310; P280-P305+P351+P338-P302+P352-P304+P340-P310
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1992 3/PG 2; UN 2810 6.1/PG 1; UN 2929 6.1/PG 1
• 欧盟补充危害声明: May form explosive peroxides.
• 保存温度: 2-8°C

产品相关信息

• 纯度: ~97-98%; ≥98.0% (GC); ≥99%; 97%; 97+%; 99%
• 浓度: 1.0 M in THF; 2 M in ethyl acetate; 2 M in methylene chloride; 2 M in THF
• 级别: purum; reagent grade; ReagentPlus®
• 线性分子式: [(CH3)3COCO]2O; O[CO2C(CH3)3]2

详细说明

MP Biomedicals - 02150859

Purity: ~97-98%
Reagent for synthesis of t-Boc amino acids.

Apollo Scientific Ltd - OR28895

Reagent for the preparation of t-Boc protected amines

Sigma Aldrich - 703737

包装
100 mL in glass bottle

Sigma Aldrich - 361941

Application
用于引入叔丁氧羰基保护基团的试剂。
通过 Lewis 酸催化作用可以保护叔丁氧羰基衍生物等醇类。
包装
5, 25 g in poly bottle
Warning
水解为叔丁醇和 CO2；暴露在潮湿环境中会导致瓶内压力增大。
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 34660

Application
用于引入叔丁氧羰基保护基团的试剂。
Other Notes
用于在氨基酸、多肽和蛋白质中清除和快速引入酸不稳定的丁氧羰基保护基团的试剂；1酰胺的 N-BOC 基化；2,3无水条件下敏感化合物的 N-BOC 基化。4
Warning
水解为叔丁醇和 CO2；暴露在潮湿环境中会导致瓶内压力增大。

Sigma Aldrich - 50431

Application
用于引入叔丁氧羰基保护基团的试剂。
Warning
水解为叔丁醇和 CO2；暴露在潮湿环境中会导致瓶内压力增大。

Sigma Aldrich - 199133

Application
用于引入叔丁氧羰基保护基团的试剂。
包装
100 g in poly bottle
Warning
水解为叔丁醇和 CO2；暴露在潮湿环境中会导致瓶内压力增大。

Sigma Aldrich - 205249

Application
三叔丁氧羰基保护的肼可以在发色试剂中制备芴甲氧羰基酯以监测固相醛类。
用于制备叔丁氧羰基保护的胺类的试剂。
用于引入叔丁氧羰基保护基团的试剂。
通过 Lewis 酸催化作用可以保护叔丁氧羰基衍生物等醇类。
通过叔丁氧羰基氨基丙炔与甲醛、二异丙胺以及溴化铜的反应来制备氨甲基丙二烯，是许多牛血浆胺氧化酶灭活剂的组分。1
包装
1 kg in amber poly
10, 50, 100 g in poly bottle
15 kg in poly drum
Warning
水解为叔丁醇和 CO2；暴露在潮湿环境中会导致瓶内压力增大。
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 703753

包装
100 mL in Sure/Seal™

Sigma Aldrich - 436267

包装
100, 800 mL in Sure/Seal™

Sigma Aldrich - 703745

包装
100 mL in Sure/Seal™

Toronto Research Chemicals - B691045

Reagent commonly used in organic chemistry for the introduction of the BOC protecting group.

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).