18-クラウン 6-エーテル
18-Crown-6
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基本情報
- CAS
17455-13-9- 標準SMILES
C1COCCOCCOCCOCCOCCO1- InChIKey
XEZNGIUYQVAUSS-UHFFFAOYSA-N- 分子式
- C12H24O6
- 平均分子量
- 264.31 g/mol
- 単同位体質量
- 264.15728849
概要
18-crown-6 is a crown ether that is cyclooctadecane in which the carbon atoms at positions 1, 4, 7, 10, 13 and 16 have been replaced by oxygen atoms. It has a role as a phase-transfer catalyst. It is a saturated organic heteromonocyclic parent and a crown ether.
名称と識別子
- 優先名称
- 18-Crown-6
- IUPAC
- 1,4,7,10,13,16-hexaoxacyclooctadecane
- 現地名
- 18-クラウン 6-エーテル
- 英語名
- 18-Crown-6
- 分子式
- C12H24O6
- 分子量
- 264.32
名称と別名
18-Crown-617455-13-91,4,7,10,13,16-HEXAOXACYCLOOCTADECANEEthylene oxide cyclic hexamerCHEBI:3239763J177NC5BNSC-159836DTXSID7058626RefChem:79335DTXCID5032313241-473-518-crown-6-ether
名称をさらに表示
18-クラウン 6-エーテル1,4,7,10,13,16-ヘキサオキサシクロオクタデカン18-クラウン-618-クラウン6-エーテル18クラウン-6エテル18-クラウン 6-エ-テル18-クラウン-6-エーテル18‐クラウン‐618-クラウン-6, 99%18-c-68-Crown-6HEXAOXACYCLOOCTADECANE18-Crown ether-6NSC 15983618-Crown-6 99%
18-Crown-6 ether18-Crown 6-EtherMFCD0000511318-crown61,4,7,10,13,16-Hexaoxacyclooctadecane (18-Crown-6)CHEMBL155204CCRIS 3587EINECS 241-473-5
データベース識別子
- CAS
17455-13-9- PubChem CID
- 28557
- DTXSID
DTXSID7058626- ChEMBL
CHEMBL155204- ChEBI
CHEBI:32397- UNII
- 63J177NC5B
- EC Number
- 241-473-5
- Nikkaji
- J49.431C
物性
構造計算による物性補完中
- XLogP
- -0.7
- 極性表面積
- 55.4 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 6
- 回転可能結合数
- 0
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 108
実験および物理化学的性質
Chemical Classes
Other Classes -> Other Organic Compounds
Industrial compound
SpringerMaterials PropertiesChemical shift
LogP-0.68
Vapor Pressure0.0000667 [mmHg]
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical DescriptionClear, odorless, hygroscopic liquid soluble in water and most organic solvents; [Ullmann] White crystals; [MSDSonline]
物理化学的性質
- 融点
- 42 · 42-45 °C(lit.)
- 沸点
- 116 °C · 116°C 0,2mm
- 比重(密度)
- 1 · 1,175 g/cm3
- 屈折率
- 1.458 · 1.4580 (estimate)
- 闪点
- 230 °F · >230 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- クロロホルム（微量）、メタノール（微量）
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Warning
H302 (98.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 314 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: 1,4,7,10,13,16-Hexaoxacyclooctadecane
Crown ether 18-crown-6: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
If absorbed, can cause electrolyte imbalance affecting the CNS; Signs of intoxication include hyperventilation, tremor, incoordination, and CNS depression; May damage the skin and eyes; LD50 (mouse) by ingestion is 0.7 g/kg; LD50 (rabbit) by skin absorption is 200 mg/kg; [Ullmann] Toxic by ingestion; A skin, eye, and respiratory tract irritant; Oral LD50 (rat) = 525 mg/kg; Dermal LDLo (rat) = 7000 mg/kg; High-dose feeding causes seizures, weight loss, and liver injury in experimental animals; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (98.7%)
毒性情報
Adverse EffectsNeurotoxin - Other CNS neurotoxin
安全データ
- F
- 10
- wgk
- 3
- tsca
- TSCA listed
化学と産業
用途と製造
UsesDrug/ Therapeutic Agent; [ChemIDplus] Used as complexing agents with ammonium ions and metal ions (alkali and alkaline-earth metals); Used as catalysts to make organic chemicals; [Ullmann]
General Manufacturing Information1,4,7,10,13,16-Hexaoxacyclooctadecane: ACTIVE
応用分野
用途クラウンエーテル類は相間移動触媒として有用である。18-クラウン-6存在下、過マンガン酸カリウムはベンゼンに溶解する。しかし、この目的には第四級アンモニウム/ホスホニウム塩の利用の方が優れている。
用途有機合成触媒、金属の濃縮、分離、回収。
使用18-Crown-6 is used as an efficient phase transfer catalyst and as a complexing agent with a variety of small cation. It is involved in the synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6. It facilitates the solubility of potassium permanganate in benzene, which is used for oxidizing the organic compounds. It is used to accelerate various substitution reactions as well as enhances the power of nucleophiles such as potassium acetate. It is utilized in the alkylation reactions in the presence of potassium carbonate, N-alkylation of glutarimide and succinimide with dimethylcarbonate. The complex formed by its reaction with potassium cyanide acts as a catalyst in the cyanosilylation of aldehydes, ketones and quinines with trimethylsilyl cyanide (TMSCN).
一般的な説明18-Crown-6 is the simplest crown ether that can be prepared by reacting triethylene glycol with triethylene glycol dichloride in the presence of potassium hydroxide as a base. 18-Crown-6 can solubilize metal salts, particularly potassium salts, in nonpolar and dipolar aprotic solvents. Thus, it is widely used as a phase transfer catalyst. It can also be used as a metal complexing agent to prepare a variety of molecular complexes.
調製方法
純化方法Recrystallise it from acetonitrile and dry it in a vacuum. Purify it also by precipitating the 18-crown-6/nitromethane 1:2 complex with Et2O/nitromethane (10:1 mixture). The complex is decomposed in vacuum whereby 18-crown-6 distils off under the reduced pressure. [Beilstein 19/12 V 601.]
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