1,4-diazabicyclo[2.2.2]octane

• ChemBase编号: 104899
• 分子式: C6H12N2
• 平均质量: 112.17288
• 单一同位素质量: 112.10004839
• SMILES: C1CN2CCN1CC2
• Canonical SMILES: C1CN2CCN1CC2
• InChI: InChI=1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2
• InChIKey: IMNIMPAHZVJRPE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,4-diazabicyclo[2.2.2]octane
• IUPAC传统名: dabco
• 别名: 1,4-二叠氮双环[2.2.2]辛烷 溶液; 1,4-二氮双环[2.2.2]辛烷; 三乙烯二胺; 1,4-二叠氮双环[2.2.2]辛烷; 1,4-Diazabicyclo[2.2.2]octane solution; Dabco® 33-LV; triethylenediamine, TEDA; DABCO; 1,4-Diazabicyclo[2.2.2]octane; TEDA; DABCO; Triethylenediamine; 1,4-DIAZABICYCLO-[2.2.2]OCTANE; 1,4-DIAZABICYCLO-(2,2,2)-OCTANE; 1,4-DIAZABICYCLO-(2.2.2)OCTANE; TED; 1,4-Diazabicyclo[2.2.2]octane

登记号

• CAS号: 280-57-9
• EC号: 205-999-9
• MDL号: MFCD00006689
• Beilstein号: 103618
• 默克索引号: 149669
• PubChem SID: 24893714; 162093073; 24857483
• PubChem CID: 9237
• Chemspider ID: 8882
• 维基百科标题: DABCO

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -3.7987516
• LogD (pH = 7.4): -2.8268335
• Log P: -0.1342359
• 摩尔折射率: 34.0692 cm^3
• 极化性: 13.381781 Å^3
• 极化表面积: 6.48 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: Soluble, hygroscopic in water
• 外观: White crystalline powder
• 熔点: 155-160°C; 156 - 160 °C; 156-159 °C; 156-159 °C(lit.); 158 °C (316 °F); 158°C
• 沸点: 174 °C (345 °F); 174 °C; 174°C; 174-176°C
• 闪点: >110 °C; >230 °F; 143.6 °F; 62 °C; 62.22°C; 62°C(143°F)
• 密度: 1.02 g/mL; 1.02 g/mL at 25 °C(lit.); 1.14 at 28 °C (water = 1); 1.140
• 折射率: n20/D 1.4634(lit.)
• 蒸汽压: 0.45 mm Hg at 20 °C; 2.9 mmHg ( 50 °C)
• 蒸汽密度: 3.86 (air = 1)

安全信息

• 保存条件: 2-8°C, Desiccate, Store Under Nitrogen
• 保存注意事项: Hygroscopic
• RTECS编号: HM0354200
• 欧盟危险性物质标志: 易燃性(Flammable) (F); X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1325; UN1325
• 德国WGK号: 1
• 联合国危险货物等级: 3; 4.1
• 联合国危险货物包装类别(PG): 2; III
• 危险公开号: 11-22-36/37/38-52/53; 11-22-37/38-41; 22-36/37/38-52/53; R:10-22-36/37/38; R:22-36/37/38; R11 R22 R36 R37 R38 R52 R53
• 安全公开号: 26-36/37/39-60; 26-60; 26-61; S:16-26-46-36/37/39; S:25-26-36/37/39
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS05; GHS07
• GHS警示词: Danger; Warning
• 主要危害: Harmful
• GHS危险声明: H228-H302-H315-H319-H335-H412; H315-H319-H335-H412; H318-H315-H228-H302-H335
• GHS警示性声明: P210-P241-P305+P351+P338-P302+P352-P405-P501A; P210-P261-P273-P305 + P351 + P338; P261-P273-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, 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 1325 4.1/PG 2
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95.0% (NT); ≥99%; 98%
• 级别: purum; ReagentPlus®
• 简要说明: 33 wt. % solution of triethylenediamine in dipropylene glycol
• Empirical Formula (Hill Notation): C6H12N2

详细说明

MP Biomedicals - 05205945

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02157609

(DABCO: Triethylenediamine)
Purified

MP Biomedicals - 02195137

Crystalline

Sigma Aldrich - D2522

Application
清除由荧光物激发产生的自由基的抗淬灭剂。在荧光显微术中添加到封固剂中以延缓荧光素和其他荧光染料的光漂白。

Sigma Aldrich - 290734

包装
100, 500 mL in poly bottle
法律信息
DABCO 注册商标 Air Products & Chemicals, Inc.

Sigma Aldrich - D27802

General description
强位阻胺碱。
包装
2 kg in poly bottle
25, 100, 500 g in poly bottle
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

参考文献

• Promotes the cleavage of ?-keto esters in refluxing xylene directly to ketones, without the need for prior hydrolysis: J. Org. Chem., 39, 1592, 2647 (1974). Similarly, malonic esters can be cleaved to esters of substituted acetic acids: J. Org. Chem., 41, 208 (1976).
• In conjunction with palladium acetate and PEG-400 provides a reusable catalyst system for the Suzuki-Miyaura cross-coupling reaction of boronic acids: J. Org. Chem., 70, 5409 (2005).
• Dabco is a registered trademark of Air Products and Chemicals Inc.
• Forms crystalline complexes with organolithium compounds: J. Am. Chem. Soc., 87, 3276 (1965), which show enhanced reactivity, e.g. in the high yield ɑ-metallation of thioanisole by n-BuLi: J. Org. Chem., 31, 4097 (1966).
• Forms a stable crystalline complex with H₂O₂, useful as an equivalent to "anhydrous" H₂O₂: reaction with TMS chloride gives bis(TMS) peroxide, a useful OH⁺-equivalent, e.g. in the conversion of aryllithiums to phenols: Synthesis, 633 (1986).
• Catalyzes the addition of aldehydes to Michael acceptors at the ɑ-position (Baylis-Hillman reaction): Helv. Chim. Acta, 63, 413 (1984):
  
• For further illustrative example, see: Org. Synth., 75, 106 (1997). Complete reaction often takes several days at ambient temperature, while heating causes lower yields. However, it is greatly accelerated by microwave irradiation: Synlett, 444 (1994). Superior results with reduced reaction times can be achieved in aqueous medium: J. Org. Chem., 66, 5413 (2001). The use as reaction medium of tetramethylene sulfone: Tetrahedron Lett., 45, 1183 (2004), or PEG-400: Tetrahedron Lett., 45, 5865 (2004) has also been advocated. Lithium perchlorate was found to increase the reaction rate dramatically: Tetrahedron Lett., 40, 1539 (1999), as was a catalytic amount of a metal triflate, particularly La or Sm; conventional Lewis acids were ineffective: J. Org Chem., 63, 7183 (1998). For asymmetric Baylis-Hillman reaction using (1S,2R)-(-)-10,2-Camphorsultam, A15897, as chiral auxiliary, see: J. Am. Chem. Soc., 119. 4317 (1997). See also 3-Quinuclidinol, B21503. For more recent discussion and comparison of different catalysts, see: J. Org. Chem., 692 (2003). In a reinterpretaion of the mechanism, a hemiacetal interemediate has been proposed: J. Org. Chem., 70, 3980 (2005). For reviews of the Baylis-Hillman reaction, see: Tetrahedron, 44, 4653 (1988); 52, 8001 (1996).