二环己烷并-24-冠醚-8 | 17455-23-1

• 物质功能分类: 化学试剂 - 有机试剂 - 冠醚
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 二环己烷并-24-冠醚-8
• 中文别名: 二环己烷并-24-冠-8
• 英文名称: dicyclohexano-24-crown-8
• 英文别名: dicyclohexyl-24-crown-8；dicyclohexano-24-crown-8 ether；2,5,8,11,18,21,24,27-octaoxatricyclo[26.4.0.012,17]dotriacontane
• CAS: 17455-23-1
• 化学式: C₂₄H₄₄O₈
• 分子量: 460.609
• InChiKey: QMLGNDFKJAFKGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  525.41°C (rough estimate)
• 密度：
  1.102 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  T
• 安全说明：
  S26,S28,S28A,S36/37/39,S38,S45
• 危险类别码：
  R23/24/25,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2932999099
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险品运输编号：
  UN 2810

SDS

Name:	Dicyclohexano-24-Crown-8 97% Material Safety Data Sheet
Synonym:	Dibenz(B,N)(1,4,7,10,13,16,19,22)Octaoxacyclotetracosin, Tetracosahydro-
CAS:	17455-23-1

Section 1 - Chemical Product MSDS Name:Dicyclohexano-24-Crown-8 97% Material Safety Data Sheet
Synonym:Dibenz(B,N)(1,4,7,10,13,16,19,22)Octaoxacyclotetracosin, Tetracosahydro-

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
17455-23-1	Dicyclohexano-24-Crown-8	97	241-474-0

Hazard Symbols: T
Risk Phrases: 25

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic if swallowed.Hygroscopic (absorbs moisture from the air).Toxic.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Avoid runoff into storm sewers and ditches which lead to waterways.
Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Absorb spill using an absorbent, non-combustible material such as earth, sand, or vermiculite. Do not use combustible materials such as sawdust.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation.
Storage:
Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 17455-23-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear yellow
Odor: hexane-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.1020g/cm3
Molecular Formula: C24H44O8
Molecular Weight: 460.60

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, exposure to moist air or water.
Incompatibilities with Other Materials:
Moisture, strong acids, strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 17455-23-1: HO7290000 LD50/LC50:
CAS# 17455-23-1: Draize test, rabbit, eye: 50 mg Moderate; Draize test, rabbit, skin: 100 mg/24H Mild; Oral, rat: LD50 = 75 mg/kg.
Carcinogenicity:
Dicyclohexano-24-Crown-8 - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 25 Toxic if swallowed.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 17455-23-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 17455-23-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 17455-23-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  二环己烷并-24-冠醚-8 在 fluorine 、 sodium fluoride 作用下， 反应 192.0h， 以3%的产率得到perfluorodicyclohexano-24-crown-8 ether
  参考文献：
  名称：

  全氟大环化合物的合成与化学

  摘要：

  全氟大环 perfluoro-18-crown-6, perfluoro-12-crown-4, perfluoro-15-crown-5, perfluoro-cyclohexano-15-crown-5, perfluorodicyclohexano-18-crown-6, perfluorodicyclohexano-24-crown -8, 和 perfluoro-4,7,13,16,21,24-hexaoxa-1, 10-diazabicyclo[8,8,8] hexacosane(perfluorocryptand [222]) 已经通过精心控制的元素氟化制备。尽管它们的碱比它们的烃类似物弱得多，但这些全氟大环是非常稳定的材料，应该有许多应用。报告了全氟-18-冠-6 和全氟二环己基-18-冠-6 异构体的晶体结构。使用几种全氟冠醚和全氟穴状配体 [222] 的气相研究表明，此类大环顽固地结合

  DOI：

  10.1021/ja00091a022
• 作为产物：
  描述：

  二苯并-24-冠醚-8 以15%的产率得到
  参考文献：
  名称：

  KUSOV, S. Z.;LUBENETS, EH. G.;SEMIKOLENOV, V. A.;KOBRIN, V. S.;XMELNITSKI+, IZV. CO AN CCCP. XIM. N.,(1989) N, S. 62-64

  摘要：

  DOI：
• 作为试剂：
  描述：

  p-chlorobenzenediazonium tetrafluoroborate 在 二环己烷并-24-冠醚-8 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  与18元，21元和24元冠醚络合的苯二氮杂离子的去重氮率

  摘要：

  在18-crown-6、21-crown-7和dicyclohexano-24-crown-8存在下，在50°C下于1,2-二氯乙烷中对四氟硼酸苯重氮鎓和四氟硼酸-氯苯重氮鎓进行重氮化的动力学评价表明，对于具有21冠7的配合物，复合物中去重氮的速率常数最小，而形成复合物的平衡常数最大。

  DOI：

  10.1016/s0040-4039(01)81825-6

文献信息

• Sequential <i>O</i>- and <i>N</i>-Acylation Protocol for High-Yield Preparation and Modification of Rotaxanes:  Synthesis, Functionalization, Structure, and Intercomponent Interaction of Rotaxanes
  作者：Yuya Tachibana、Hiroaki Kawasaki、Nobuhiro Kihara、Toshikazu Takata

  DOI：10.1021/jo0601563

  日期：2006.7.1

  catalyst to afford the corresponding rotaxane in high yield. Large-scale synthesis without chromatographic separation was easily achieved. The ammonium group in the resulting rotaxane was quantitatively acylated with excess electrophile in the presence of excess trialkylamine. Various N-functionalized rotaxanes were prepared by this sequential double-acylation protocol. 1H NMR spectra and X-ray crystallographic

  在三丁基膦作为催化剂的存在下，由庞大的酸酐将由24元冠醚和在末端带有羟基的仲铵盐组成的拟轮烷定量酰化，从而以高收率得到相应的轮烷。无需色谱分离即可轻松实现大规模合成。在过量的三烷基胺存在下，用过量的亲电子试剂将所得轮烷中的铵基团定量酰化。通过该顺序的双酰化方案制备了各种N-官能化的轮烷。1个轮烷的1 H NMR光谱和X射线晶体学分析表明，冠状醚组分通过强的氢键键合相互作用而被捕获在铵型轮烷中的铵基上。铵基周围的构象通过氢键相互作用而固定。同时，酰胺型轮烷的构象由冠醚中的亚甲基与车轴组件的苯环之间的弱CH /π相互作用确定。铵型轮烷的N-酰化可用于制备功能化的轮烷和弱的基于组分间相互作用的轮烷。
• Efficient synthesis of [2]- and higher order rotaxanes via the transition metal-catalyzed hydrosilylation of alkyne
  作者：Hisahiro Sasabe、Nobuhiro Kihara、Kazuhiko Mizuno、Akiya Ogawa、Toshikazu Takata

  DOI：10.1016/j.tetlet.2005.03.186

  日期：2005.5

  RuHCl(CO)(PPh3)3 and RhCl(CO)(PPh3)3 complexes catalyzed the hydrosilylation reactions of the alkyne moiety of several pseudorotaxanes at ambient temperature to give the corresponding [2]- and higher order rotaxanes in high yields with excellent regio- and stereoselectivity.

  提出了一种通过轴端炔烃的氢化硅烷化对拟轮烷进行封端的新方法。RuHCl（CO）（PPh 3）3和RhCl（CO）（PPh 3）3配合物在环境温度下催化几种假轮烷的炔基部分的氢化硅烷化反应，以高收率得到相应的[2]-和更高阶的轮烷。出色的区域选择性和立体选择性。
• Dynamically capped rotaxanes: metal coordination vs. acid–base pairing in the chiral end-capping
  作者：Satoshi Shinoda、Takayuki Maeda、Hiroyuki Miyake、Hiroshi Tsukube

  DOI：10.1080/10610278.2010.521838

  日期：2011.3.1

  formed by mixing a thread molecule and several crown ethers. Crystal structure analysis clearly indicated that hydrogen bonding between NH2 + of the thread molecule and crown ether oxygen atoms was significantly involved, together with cation–dipole interactions between cationic nitrogen and ether oxygen atoms. End-capping of the pseudorotaxane with chiral metal complexes gave dynamically capped rotaxanes

  通过将一个线分子和几种冠醚混合形成一系列假轮烷。晶体结构分析清楚地表明，线分子的 NH2+ 与冠醚氧原子之间的氢键显着参与，以及阳离子氮和醚氧原子之间的阳离子 - 偶极相互作用。用手性金属配合物封端假轮烷得到动态封端的轮烷，包括 dibenzo-24-crown-8。这在苯并冠和蒽线发色团区域周围表现出诱导的圆二色性信号，而手性有机酸形成的轮烷表现出较弱的信号。
• New concept for the preparation of potassium sodides: the use of hexane as a non-polar solvent
  作者：Zbigniew Grobelny、Andrzej Stolarzewicz、Barbara Morejko-Buż、Antoni Winiarski

  DOI：10.1016/s0040-4020(03)00185-6

  日期：2003.3

  contact with 15-crown-5 hexane solution became potassium sodide K+(15-crown-5)2Na−. After the evaporation of hexane the crystalline solid product was analyzed by X-ray diffraction and the lattice parameters were calculated. The potassium sodide thus obtained could be easily dissolved in tetrahydrofuran. A deep blue solution containing sodium anions and complexed potassium cations was formed with a very

  与15-冠-5己烷溶液接触的NaK合金成为钾sodideķ +（15-冠-5）2的Na - 。蒸发己烷后，通过X射线衍射分析结晶固体产物，并计算晶格参数。由此获得的钠化钾可以容易地溶解在四氢呋喃中。形成了含有钠阴离子和复合钾阳离子的深蓝色溶液，其溶剂化电子的浓度非常低，即约为10 -7M  。在这种情况下，未检测到钾离子。一种新的结晶钾sodideķ +（DCH-24-冠8）2的Na - 用NaK合金和二环己基-24-冠-8己烷溶液制得。
• Dry optical - chemical carbon - dioxide sensor
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1972929A1

  公开（公告）日：2008-09-24

  A device for determining carbon dioxide in a gaseous or liquid sample, comprises: a polymer matrix e.g. ethyl cellulose, polysiloxanes etc. and an indicator embedded in the polymer matrix, wherein the indicator comprises a pH-sensitive dye e.g. bromothymol blue, HPTS etc. and a lipophilic, metal cation-ionophore complex e.g. K-18-crown-6, and wherein an anion of the pH-sensitive dye and the metal cation-ionophore complex form an ion-pair which is soluble in the polymer matrix.

  一种用于测定气态或液态样品中二氧化碳含量的装置，包括：聚合物基体（如乙基纤维素、聚硅氧烷等）和嵌入聚合物基体中的指示剂，其中指示剂包括对 pH 值敏感的染料（如溴百里酚蓝、HPTS 等）和亲油的金属阳离子-亲离子络合物（如 K-18-冠醚-6）。其中指示剂包括对 pH 值敏感的染料（如溴百里酚蓝、HPTS 等）和亲油的金属阳离子-嗜离子络合物（如 K-18-冠醚-6），其中对 pH 值敏感的染料的阴离子和金属阳离子-嗜离子络合物形成离子对，可溶于聚合物基质中。

表征谱图