18-Crown-6 18-冠醚-6

CAS 17455-13-9 MFCD00005113

化学结构图

17455-13-9
SMILES: C1COCCOCCOCCOCCOCCO1

化学属性

Mol. FormulaC12H24O6
Mol. Weight264.32
Melting Point42-45°C
Density1.175
Flash Point>113°C
TSCAYes
Boiling Point395.8°C at 760 mmHg
Solubility可溶
Appearance #EndEditable "Content" 无色粘稠液,沸点115-116℃(240Pa),93-96℃(18.3Pa),78℃(6.67Pa),相对密度1.113(20/4℃),折光率1.4615。18-Grown-6,1,4,7,10,13,16-Hexaoxacy-clooctadecane,白色结晶。熔点38-39.5℃,沸点116℃(26.6Pa)。冠醚又称大环醚,是含有多个氧原子的大环化合物。命名时,把环上所含原子的总数标注在“冠”字之前,其中所含氧原子数标注在名称之后。这是杜邦公司的Pedersen在1967年意外发现的,并发现这类化合物具有许多异常的特性。 用途:冠醚最主要的特点之一,是可与各种金属盐、铵盐、有机阳离子化合物等形成稳定的络合物。利用这一性质,可将各种盐类溶于有机溶剂。冠醚可将阳离子螯环内,同时由于有朝外的有机基因可生成络合物,亦可溶于非极性的有机溶剂。这时,未被溶剂化的阴离子,以裸露的阴离子形式存在于溶剂中,故活性极大。冠醚可使碱金属和有机碱金属化合物溶解在有机溶剂中。因而在有机合成、光学拆分、重金属螯合、分离、分析以及生理活性的医药、生物化学等方面找到广泛的应用。例如,用作相转移催化剂,使许多在传统条件下难以反应,甚至不发生的反应,能顺利地进行,这类反应速率快、条件简单、操作方便、产率高。例如,安息香在水溶液中的缩合反应产率极低,如果在该水溶液中加入7%的冠醚,则可得到产率为78%的安息香。这一反应还可在苯(或乙腈)中进行,尽管氰化钾不溶于苯,但如果加入18-冠-6,则不仅能发生反应,而且产率可高达95%。18-冠-6的毒性:大鼠的口服致死量为300mg/kg。对眼睛、皮肤有刺激性。 制备方法:通常采用威廉林合成法制取,即用醇盐与卤代烷反应。
Stability热和湿度敏感

别名和识别编码

Chemical Name18-Crown-6
CAS Number17455-13-9
Synonym 18-Crown-6-ether {LY} 18-Crown-6-ether {} {LY} 18-Crown-6-ether {} {} {LY} 18-Crown-6-ether {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 18-Crown-6-ether {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID87565919
EC Number241-473-5
Beilstein Registry Number1619616
MDL NumberMFCD00005113
Reaxys-RN1619616
Merck Number2602
Chemical Name Translation18-冠醚-6
Wiswesser Line NotationT-18-O DO GO JO MO POTJ
LabNetwork Molecule IDLN00198526
Canonical SMILESO1CCOCCOCCOCCOCCOCC1
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分类

  • Alkylation Reagents, Analytical Reagents, Analytical/Chromatography, Chelation/Complexation Compounds, Chemical Synthesis,
  • {SNA} Analytical Reagents, Analytical/Chromatography, Chromatography Reagents & Solvents, Ion Chromatography Reagents, Salts and Additives for IC
  • {SNA} Chelation/Complexation Compounds, Chemical Synthesis, Crown Ethers, Synthetic Reagents
  • {uni_hamburg} no charge; oxygen heterocycle; alicycle; large ring; crown ether; 18ring; ether; 1fragment
  • {SNA} Chromatography Reagents & Solvents, Ion Chromatography Reagents, Salts and Additives for IC, 分析/色谱, 分析试剂
  • {SNA} 12 Principles Aligned Products, Chelation/Complexation Compounds, Chemical Synthesis, Crown Ethers, Greener Alternative Products, Synthetic Reagents

产品应用

  • 大环醚类有机化合物。主要用途为精细有机合成用高效相转移催化剂、络合剂、贵金属和稀土元素分离提取用萃取剂。在化学分析中可用于离子的富集、分离和掩蔽,还可用于医药、生物化学领域以及电子工业中用作离子导电材料、液晶显示元件制作材料。

相关文献及参考

  • Crown et
  • Beil. 19 ,V,12,601
  • Has been widely used in alkylation reactions with, e.g. K2CO3 as base:
  • 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 cata
  • 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).
  • 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).
  • 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).

安全信息

GHS Symbol
WGK Germany3
Hazard Codes Xn Xn,Xi
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H302 Harmful if swallowed 吞食有害
  • H319 Causes serious eye irritation 严重刺激眼睛
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
RTECSMP4500000
Precautionary statements
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P332+P313
  • P305+P351+P338+P337+P313
  • P301+P312+P330
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P302+P350
Signal word {} {} {} {} {TCI}
Storage condition 2-8°C, sealed storage, away from moisture {LY} 2-8°C, sealed storage, away from moisture {} {LY} 2-8°C, sealed storage, away from moisture {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, awa
Safety Statements
  • S39 Wear eye/face protection 戴眼睛/面孔保护装置;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
Risk Statements
  • R36 Irritating to eyes 刺激眼睛
  • R20/22 Harmful by inhalation and if swallowed 吸入和不慎吞咽有害
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Packing GroupIII
Hazard Class6.1(b)
UN Number 2811
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   RPTOAN Russian Pharmacology and Toxicology (English Translation).
   Translation of FATOAO.  (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey,
   UK)  V.30-    1967-  Volum

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 540 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   GISAAA Gigiena i Sanitariya.  For English translation, see HYSAAV.  (V/O
   Mezhdunarodnaya Kniga, 113095 Moscow, USSR)  V.1-    1936-
   Volume(issue)/page/year: 53(10),92,1988

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intratracheal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 56 mg/kg
TOXIC EFFECTS :
   Behavioral - tremor
   Lungs, Thorax, or Respiration - structural or functional change in trachea
   or bronchi
   Lungs, Thorax, or Respiration - fibrosis, focal (pneumoconiosis)
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: OTS0536187

TYPE OF TEST            : LD - Lethal dose
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >2500 mg/kg
TOXIC EFFECTS :
   Behavioral - tremor
   Gastrointestinal - other changes
   Liver - other changes
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.

其他信息

  • 用途一:用作金属离子络合剂
  • 用途三:大环醚类有机化合物。主要用途为精细有机合成用高效相转移催化剂、络合剂、贵金属和稀土元素分离提取用萃取剂。在化学分析中可用于离子的富集、分离和掩蔽,还可用于医药、生物化学领域以及电子工业中用作离子导电材料、液晶显示元件制作材料。
  • TCI Shanghai:18-冠-6-醚 18-Crown 6-Ether,>;98.0%(GC)(17455-13-9)
  • MOL 文件:17455-13-9.mol
  • 检测方法:GC,NMR,MS
  • 18-冠醚-6价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30203262 十八冠醚-6 100g 320元 2011/04/16 C0860 18-冠6-醚 18-Crown 6-Ether 100G 2460元 2011/04/16 C0860 18-冠6-醚 18-Crown 6-Ether 25G 880元
  • MSDS 信息:Hexaoxacyclo-octadecane(17455-13-9).msds
  • 上游原料:氰化钾 --> 碱金属 --> 15-冠醚-5 --> Γ-球蛋白 --> 有机碱 --> 生物化学
  • 图谱信息:18-冠醚-6(17455-13-9)核磁图( 1 HNMR) 18-冠醚-6(17455-13-9)核磁图( 13 CNMR) 18-冠醚-6(17455-13-9)质谱(MS) 18-冠醚-6(17455-13-9)红外图谱(IR2) 18-冠醚-6(17455-13-9)红外图谱(IR1)
  • 海关编码:29329995
  • 用途二:冠醚最主要的特点之一,是可与各种金属盐、铵盐、有机阳离子化合物等形成稳定的络合物。利用这一性质,可将各种盐类溶于有机溶剂。冠醚可将阳离子螯环内,同时由于有朝外的有机基因可生成络合物,亦可溶于非极性的有机溶剂。这时,未被溶剂化的阴离子,以裸露的阴离子形式存在于溶剂中,故活性极大。冠醚可使碱金属和有机碱金属化合物溶解在有机溶剂中。因而在有机合成、光学拆分、重金属螯合、分离、分析以及生理活性的医药、生物化学等方面找到广泛的应用。例如,用作相转移催化剂,使许多在传统条件下难以反应,甚至不发生的反应,
  • 存储注意事项:氮气保护
  • 敏感性:Hygroscopic
  • F:10
  • Acros Organics:18-冠醚-6 18-Crown-6, 99%(17455-13-9)
  • 下游产品:二甲基二茂铁 --> N,N-二甲基乙二胺 --> 5-溴吲唑 --> 3-苯氧基苯乙腈 --> 1,3-噻唑烷-2-酮 --> 头孢泊肟酯 --> 环氧十二烷 --> 2,4-二氨基-6-氟嘧啶 --> [(2-氧代-2H-苯并吡喃-7-基)氧基]乙酸 --> 4-甲基-3-氨基-2-氟吡啶 --> 2-氨基-4,6-二氟嘧啶 --> 2-(4-溴苯基)噻吩 --> 4-氨基-2,6-二氟嘧啶 --> N,N,N',N'-四苯基联苯胺
  • 方法一:通常采用威廉林合成法制取,即用醇盐与卤代烷反应。 用途:冠醚最主要的特点之一,是可与各种金属盐、铵盐、有机阳离子化合物等形成稳定的络合物。利用这一性质,可将各种盐类溶于有机溶剂。冠醚可将阳离子螯环内,同时由于有朝外的有机基因可生成络合物,亦可溶于非极性的有机溶剂。这时,未被溶剂化的阴离子,以裸露的阴离子形式存在于溶剂中,故活性极大。冠醚可使碱金属和有机碱金属化合物溶解在有机溶剂中。因而在有机合成、光学拆分、重金属螯合、分离、分析以及生理活性的医药、生物化学等方面找到广泛的应用。例如,用作相转移催化剂,使许多在传统条件下难以反应,甚至不发生的反应,能顺利地进行,这类反应速率快、条件简单、操作方便、产率高。例如,安息香在水溶液中的缩合反应产率极低,如果在该水溶液中加入7%的冠醚,则可得到产率为78%的安息香。这一反应还可在苯(或乙腈)中进行,尽管氰化钾不溶于苯,但如果加入18-冠-6,则不仅能发生反应,而且产率可高达95%。18-冠-6的毒性:大鼠的口服致死量为300mg/kg。对眼睛、皮肤有刺激性。 #EndEditable "Content"

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