1,4,7,10,13,16-hexaoxacyclooctadecane

• ChemBase编号: 75098
• 分子式: C12H24O6
• 平均质量: 264.31536
• 单一同位素质量: 264.15728849
• SMILES: O1CCOCCOCCOCCOCCOCC1
• Canonical SMILES: O1CCOCCOCCOCCOCCOCC1
• InChI: InChI=1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2
• InChIKey: XEZNGIUYQVAUSS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,4,7,10,13,16-hexaoxacyclooctadecane
• IUPAC传统名: 18-crown-6 ether
• 别名: 18-冠-6醚; 1,4,7,10,13,16-六氧环十八烷; 18-冠醚-6; 18-Crown-6; 1,4,7,10,13,16-Hexaoxacyclooctadecane 99%; 1,4,7,10,13,16-Hexaoxacyclooctadecane; 18-CROWN-6; 18-Crown-6; 1,4,7,10,13,16-hexaoxacyclooctadecane; 18-Crown-6 ether; Ethylene Oxide Cyclic Hexamer; NSC 159836

登记号

• CAS号: 17455-13-9
• EC号: 241-473-5
• MDL号: MFCD00005113
• Beilstein号: 1619616
• 默克索引号: 142602
• PubChem SID: 24851233; 162040016; 24846099; 24856618
• PubChem CID: 28557
• CHEBI ID: 32397
• CHEMBL: 155204
• Chemspider ID: 26563
• 维基百科标题: 18-Crown-6

理论计算性质

• 质子受体: 6
• 质子供体: 0
• LogD (pH = 5.5): -0.28185305
• LogD (pH = 7.4): -0.28185305
• Log P: -0.28185305
• 摩尔折射率: 66.261 cm^3
• 极化性: 26.357956 Å^3
• 极化表面积: 55.38 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

• 熔点: 37–40 °C; 37-41°C; 37-45°C; 38-41 °C; 40-45°C; 42 - 45°C; 42-45 °C(lit.)
• 沸点: 116°C/0.2mm; 116 °C (0.2 Torr); 116°C/0.2mm
• 闪点: > 110°C; >113 °C; >235.4 °F; 109°C; 109°C(228°F)
• 密度: 1.175; 1.237 g/cm3
• 疏水性(logP): -1.182

安全信息

• 保存条件: 2-8°C
• 保存注意事项: Harmful/Irritant/Hygroscopic/Store under Argon; Hygroscopic
• RTECS编号: MP4500000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+); X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2810
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): I
• 澳大利亚Hazchem: 2XE
• 危险公开号: 22-36; 22-36/37/38; R:22-27
• 安全公开号: 26-36; S:28-29-36/37/39-45
• 欧盟危险货物分类: T1
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 153
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H335; H302-H319-H313
• GHS警示性声明: P261-P305 + P351 + P338; P280-P305+P351+P338-P301+P312-P312-P337+P313-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥99.0%; ≥99.0% (GC); 95%; 95+%; 99%
• 级别: for ion chromatography; purum
• 痕量阳离子: Al: ≤1 mg/kg; Ba: ≤1 mg/kg; Bi: ≤1 mg/kg; Ca: ≤5 mg/kg; Cd: ≤1 mg/kg; Co: ≤1 mg/kg; Cr: ≤1 mg/kg; Cu: ≤1 mg/kg; Fe: ≤1 mg/kg; K: ≤1 mg/kg; Li: ≤1 mg/kg; Mg: ≤1 mg/kg; Mn: ≤1 mg/kg; Mo: ≤1 mg/kg; Na: ≤20 mg/kg; NH4+: ≤50 mg/kg; Ni: ≤1 mg/kg; Pb: ≤1 mg/kg; Sr: ≤1 mg/kg; Zn: ≤1 mg/kg
• Empirical Formula (Hill Notation): C12H24O6

详细说明

MP Biomedicals - 02150731

Phase transfer catalyst and complexing-agent.

Sigma Aldrich - C5515

Application
有效用作相转移催化剂。
Other Notes
具有重复 (-CH2CH2O) 单元的大环聚醚。该化合物为离子载体型(与阳离子形成稳定的复合物)。

Sigma Aldrich - 186651

Application
有效用作相转移催化剂。
用于化学选择性还原熔融四氮唑和 NaBH4 以及氢氧化钾的相转移催化剂。
Other Notes
具有重复 (-CH2CH2O) 单元的大环聚醚。该化合物为离子载体型(与阳离子形成稳定的复合物)。
包装
5, 25 g in glass bottle

Sigma Aldrich - 274984

Application
可在非极性溶剂中溶解阳离子的络合剂。
有效用作相转移催化剂。
Other Notes
具有重复 (-CH2CH2O) 单元的大环聚醚。该化合物为离子载体型(与阳离子形成稳定的复合物)。
包装
1 g in glass bottle

Sigma Aldrich - 07673

Application
有效用作相转移催化剂。
Other Notes
具有重复 (-CH2CH2O) 单元的大环聚醚。该化合物为离子载体型(与阳离子形成稳定的复合物)。

Sigma Aldrich - 28125

Application
有效用作相转移催化剂。
Other Notes
具有重复 (-CH2CH2O) 单元的大环聚醚。该化合物为离子载体型(与阳离子形成稳定的复合物)。
相转移催化剂，络合剂1,2

Toronto Research Chemicals - C824875

A useful phase transfer catalyst.

参考文献

• Crown ether (see Appendix 2) mainly used to complex potassium ions. For a comprehensive study of solvent effects on complexation with K ions in a wide range of solvents, see: J. Org. Chem., 61, 5221 (1996).
• Promotes methylation reactions with Dimethyl carbonate, A13104: Synthesis, 382 (1986). N-Alkylation of Glutarimide, L00968, and Succinimide, A13503: Bull. Soc. Chim. Fr., 227 (1992).
• Enables KH to metallate aryl-substituted methanes directly: J. Am. Chem. Soc., 99, 4457 (1977). In the presence of KOH in DME, various arylmethanes, benzyl alcohols and aldehydes are oxidized to carboxylic acids by molecular oxygen: Tetrahedron Lett., 25, 4989 (1984).
• Has been used with KF to enhance the reactivity of F^- as a base or a nucleophile, e.g. to promote Michael additions in aprotic solvents: J. Chem. Soc., Chem. Commun., 237 (1977), the condensation of nitromethane with aldehydes: Tetrahedron Lett., 3219 (1978), and the transesterification of diaryl to dialkyl phosphonates: Synthesis, 409, 412 (1982).
• Crown ether catalysis can be used in the reaction of KCN with alkyl halides to give nitriles: Tetrahedron Lett., 71 (1975), and for the preparation of acyl cyanides from acid chlorides: Tetrahedron Lett., 21, 2959 (1980). The 1:1 complex between 18-crown-6 and KCN has been used catalytically in the cyanosilylation of aldehydes, ketones and quinones with TMSCN; for examples, see: Org. Synth. Coll., 7, 517 (1990).
• Has been widely used in alkylation reactions with, e.g. K₂CO₃ as base: