ジベンゾ-18-クラウン6-エーテル

Dibenzo-18-crown-6

HCID 26541CAS 14187-32-7
部分構造検索類似構造を探す

基本情報

標準SMILES
c1ccc2c(c1)OCCOCCOc1ccccc1OCCOCCO2
InChIKey
YSSSPARMOAYJTE-UHFFFAOYSA-N
分子式
C20H24O6
平均分子量
360.4 g/mol
単同位体質量
360.15728849

概要

Dibenzo-18-crown-6 is a crown ether that is 18-crown-6 ortho-fused to two benzene rings at positions 8-9 and 17-18. It has a role as a phase-transfer catalyst. It is a member of benzenes and a crown ether.

名称と識別子

優先名称
Dibenzo-18-crown-6
IUPAC
2,5,8,15,18,21-hexaoxatricyclo[20.4.0.09,14]hexacosa-1(26),9,11,13,22,24-hexaene
現地名
ジベンゾ-18-クラウン6-エーテル
英語名
Dibenzo-18-crown-6
分子式
C20H24O6
分子量
360.4

名称と別名

DIBENZO-18-CROWN-614187-32-7Dibenzo-18-crown-6-etherCrown 18Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-2,3:11,12-Dibenzo-1,4,7,10,13,16-hexaoxacyclooctadecane0A7W45JCS9Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecane2,5,8,15,18,21-hexaoxatricyclo[20.4.0.09,14]hexacosa-1(26),9,11,13,22,24-hexaeneNSC-147771Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecaneDTXSID6022428
名称をさらに表示
ジベンゾ-18-クラウン6-エーテル2,2'-[オキシビス(エチレンオキシ)][1,1'-[オキシビス(エチレンオキシ)]ビスベンゼン]2,2'-[オキシビス(エチレンオキシ)]-[1,1'-[オキシビス(エチレンオキシ)]ビスベンゼン]1,2-[1,2-フェニレンビス(オキシエチレンオキシエチレンオキシ)]ベンゼンジベンゾ-18-クラウン-61,2-[2,1-フェニレンビス(オキシエチレンオキシエチレンオキシ)]ベンゼン6,7,9,10,17,18,20,21-オクタヒドロ-5,8,11,16,19,22-ヘキサオキサジベンゾ[a,j]シクロオクタデセン3,6,9,12,15,18-ヘキサオキサ-1,2:10,11-ジベンゾ-1,10-シクロオクタデカジエン6,7,9,10,17,18,20,21-オクタヒドロ-ジベンゾ[b,k][1,4,7,10,13,16]ヘキサオキサシクロオクタデシン6,7,9,10,17,18,20,21-オクタヒドロジベンゾ[b,k][1,4,7,10,13,16]ヘキサオキサシクロオクタデシン1,1'-(1,2-フェニレン)-7,7'-(1,2-フェニレン)ビス(1,4,7-トリオキサヘプタン)ジベンゾ[18]クラウン-6クラウンエーテル/ジベンゾ-18-クラウン-6クラウンエーテル/ジベンゾ‐18‐クラウン‐6ジベンゾ‐18‐クラウン‐6ジベンゾ-18-クラウン-6, min. 98%2,2′-[オキシビス(エチレンオキシ)]-[1,1′-[オキシビス(エチレンオキシ)]ビスベンゼン]1,1′-[オキシビス(エチレンオキシ)]-2,2′-[オキシビス(エチレンオキシ)]ビスベンゼン2,5,8,15,18,21-ヘキサオキサトリシクロ[20.4.0.09,14]ヘキサコサ-1(26),9,11,13,22,24-ヘキサエン1,1′-(1,2-フェニレン)-7,7′-(1,2-フェニレン)ビス(1,4,7-トリオキサヘプタン)DB18C6ibenzo-18-crown-66,7,9,10,12,13,15,16-Octahydrodibenzo[b,e][1,4,7,10,13,16]hexaoxacyclooctadecinecrown18crown-18DibenzocrownDibenzo-18-crown-8
CHEBI:358732Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-2,5,8,15,18,21-hexaoxatricyclo(20.4.0.09,14)hexacosa-1(26),9,11,13,22,24-hexaeneRefChem:132840DTXCID802428238-041-36,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecineMFCD00005098

データベース識別子

CAS
14187-32-7
PubChem CID
26541
DTXSID
DTXSID6022428
ChEMBL
CHEMBL345536
ChEBI
CHEBI:358732
UNII
0A7W45JCS9
EC Number
238-041-3
Nikkaji
J14.747H

物性

構造計算による物性

XLogP
2.2
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
26

実験および物理化学的性質

Chemical ClassesOther Classes -> Other Organic Compounds
SpringerMaterials PropertiesFusion temperature
LogP2.2
Physical DescriptionLight beige fibers or powder; [Alfa Aesar MSDS]

物理化学的性質

融点
162 · 162-164 °C (lit.)
沸点
380 · 380-384 °C (679 mmHg)
比重(密度)
1.1801 · 1.1801 (rough estimate)
屈折率
1.52 · 1.5200 (estimate)
闪点
380 · 380-384°C/679mm
貯蔵温度
30 °C · Store below +30°C.

化学的性質

化学的特性white to slightly beige fluffy powder

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (35.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 64 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 2 件

Chemical: Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-

Dibenzob,k1,4,7,10,13,16hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

A mild skin and moderate eye irritant; Causes convulsions, lung changes and other liver changes in oral lethal-dose studies of rats; [RTECS] Crown ethers have caused convulsions, liver injury, and dermatitis in experimental animals; A skin and strong eye irritant; [Alfa Aesar MSDS] See 18-Crown-6.

Hazard Classes and CategoriesSkin Irrit. 2 (35.9%)

毒性情報

Adverse EffectsNeurotoxin - Other CNS neurotoxin

安全データ

wgk
2
tsca
TSCA listed
rtecs
HP5386000
毒性
LD50 orally in Rabbit: 2600 mg/kg
hs_code
29329995
risk_code
36-36/37/38-20/21/22

化学と産業

用途と製造

General Manufacturing InformationDibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-: ACTIVE
応用分野 · 3 件

用途有機合成、分析用試薬

説明Dibenzo-18-crown-6 (DB18C6) is the first crown ether synthesized by Pedersen in 1967 and has the strongest binding affinity to a potassium cation (K+) among alkali metal cations. With the similarity of the sizes between K+ and the cavity of crown ether, it had long been believed that the binding selectivity comes from the size relationship between the metal cation and the cavity. However, it was reported that under identical experimental conditions, K+ bound strongly to all crown ethers (12-crown-4 to 24-crown-8) irrespective of the ring size among other cations such as Na+, Ca2+, and NH4+. Moreover, in the gas phase, 18-crown-6 (18C6) and dibenzo18-crown-6 (DB18C6) form preferential complexation in the order Li+ > Na+ > K+ > Rb+ > Cs+, while in the aqueous solution both of them show highest complexion capacity for K+ rather than Li+[1-2].

使用Dibenzo-18-crown-6, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is an important organic intermediate.

調製方法

純化方法Crystallise it from *benzene, n-heptane or toluene and dry it under vacuum at room temperature for several days. [Szezygiel J Phys Chem 91 1252 1987, V.gtle ed. Top Corr Chem (Host Guest Complex Chemistry) 98 1981.]

上流・下流製品情報

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