4'-甲酰苯并-18-冠-6-醚 | 60835-74-7

• 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: 4'-甲酰苯并-18-冠-6-醚
• 中文别名: 4’-甲酰苯并-18-冠-6-醚
• 英文名称: 4'-formyl-benzo-18-crown-6-ether
• 英文别名: 4'-formylbenzo-18-crown-6；4’-formylbenzo-18-crown-6；2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecine-18-carbaldehyde；4′-formylbenzo-18-crown-6 ether；4'-Formylbenzo-18-crown 6-Ether；2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(18),19,21-triene-20-carbaldehyde
• CAS: 60835-74-7
• 化学式: C₁₇H₂₄O₇
• 分子量: 340.373
• InChiKey: ALMXRNQJWRGNMG-UHFFFAOYSA-N

物化性质

• 熔点：
  59-61 °C(Solv: ethanol (64-17-5))
• 沸点：
  506.4±50.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避免接触氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319
• 储存条件：
  在密封的贮藏器中存放，并置于阴凉、干燥处保存。

SDS

4'-Formylbenzo-18-crown 6-Ether Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 4'-Formylbenzo-18-crown 6-Ether

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Acute toxicity (Oral) Category 5
Category 2
Skin corrosion/irritation
Serious eye damage/eye irritation Category 2A
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements May be harmful if swallowed
Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.
Call a POISON CENTER or doctor/physician if you feel unwell.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 4'-Formylbenzo-18-crown 6-Ether
Percent: >98.0%(GC)
CAS Number: 60835-74-7
2,3-(4-Formylbenzo)-1,4,7,10,13,16-hexaoxacyclooctadec-2-ene
Synonyms:
Chemical Formula: C17H24O7
4'-Formylbenzo-18-crown 6-Ether

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Call a POISON CENTER or doctor/physician if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Air-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
4'-Formylbenzo-18-crown 6-Ether

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Colour: White - Pale yellow green
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Chemical stability:
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
No data available
Henry's Law
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
4'-Formylbenzo-18-crown 6-Ether

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4'-甲酰苯并-18-冠-6-醚 在 palladium on activated charcoal 吡啶 、 氢气 、 四氯化钛 、 1,8-双二甲氨基萘 、 锌 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， -78.0~90.0 ℃ 、300.0 kPa 条件下， 反应 21.5h， 生成 1,2-bis-(4-benzo-18-crown-6)ethane
  参考文献：
  名称：

  Lindsten, Goeran; Wennerstroem, Olof; Thulin, Bengt, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 7, p. 545 - 554

  摘要：

  DOI：
• 作为产物：
  描述：

  以 乙腈 为溶剂， 生成 4'-甲酰苯并-18-冠-6-醚
  参考文献：
  名称：

  氮原子与苯环共轭的N-甲基苯并氮杂row草醚：改进的合成及其与金属和铵阳离子配合物高稳定性的原因

  摘要：

  提出了一种改进的合成N-甲基苯并氮杂氮杂呋喃醚甲酰基衍生物的方法。它们可通过更少的步骤以最高68％的产率制备，并且最后一步所需的时间要短得多。通过在CD 3 CN中1 H NMR滴定确定由N-甲基苯并氮杂row杂醚及其结构类似物与碱金属，碱土金属和铵阳离子形成的配合物的稳定常数。N配合物的高稳定性结果表明，苯并氮杂皇冠醚的甲基衍生物与苯并冠醚配合物的稳定性相当甚至超过其稳定性，并显着超过了具有相同大环尺寸的苯并氮杂醚的配合物的稳定性。通过X射线衍射研究了氮杂冠醚及其与Ba（ClO 4）2的配合物的结构。注意到N-甲基苯并氮杂row草醚高度预组织化与金属和铵阳离子形成配合物，这是由于氮原子的金字塔形状清晰且孤电子对（LEPs）的取向大部分杂原子朝向大杂环中心。版权所有©2009 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.1527

文献信息

• New Applications of Crown Ethers. II. Synthesis of 4′-Formylbenzocrown Ethers
  作者：Fumio Wada、Hiroshi Hirayama、Hiroshi Namiki、Kiyoshi Kikukawa、Tsutomu Matsuda

  DOI：10.1246/bcsj.53.1473

  日期：1980.5

  4′-Formylbenzo-15-crown-5, -18-crown-6, and bis(4′-formylbenzo)-18-crown-6 were conveniently synthesized in excellent yields by Smith modification of Duff reaction: formylation with hexamethylenetetramine and trifluoroacetic acid or methanesulfonic acid.

  4'-Formylbenzo-15-crown-5、-18-crown-6 和双 (4'-formylbenzo)-18-crown-6 通过 Duff 反应的 Smith 改进以优异的产率方便地合成：用六亚甲基四胺和三氟乙酸甲酰化酸或甲磺酸。
• Controlled self-assembly of bis(crown)stilbenes into unusual bis-sandwich complexes: structure and stereoselective [2+2] photocycloaddition
  作者：Sergey P. Gromov、Artem I. Vedernikov、Natalia A. Lobova、Lyudmila G. Kuz'mina、Stepan S. Basok、Yuri A. Strelenko、Michael V. Alfimov、Judith A. K. Howard

  DOI：10.1039/c0nj00780c

  日期：——

  shown by 1H NMR spectroscopy that symmetrical bis(crown)stilbenes (L) and small alkali and alkaline-earth metal cations form 1(L) ∶ 1(Mm+) and 1(L) ∶ 2(Mm+) complexes in MeCN solutions. In the case of large or hydrated metal cations such as Cs+, Rb+, K+, Ba2+, Sr2+, [Ca(H2O)x]2+ and stilbenes with a small crown-ether cavity as compared with the metal cation size, stable bis-sandwich complexes 2(L) ∶ 2(Mm+)

  它是由示出1 H NMR光谱的是对称的双（冠）芪（L）和小碱金属和碱土金属阳离子形成1（L）：1（M米+）和1（L）：2（M米+）MeCN解决方案中的复合物。在较大或水合金属阳离子（例如Cs +，Rb +，K +，Ba 2 +，Sr 2 +，[Ca（H 2 O）x ] 2+）和丁苯醚中，冠醚空穴较小的情况下与金属阳离子的大小，稳定的双夹心络合物2（L）：2（M m +）也可以形成。由双（18-冠-6）二苯乙烯与丙烷二铵离子也可制得稳定的双假夹心2：2络合物。阐明了冠醚大小，阳离子大小和性质对二苯乙烯光转化途径和产物组成的影响。双（假）三明治复合物经过有效的立体选择性[2 + 2]光环加成，主要生成新的1,2,3,4-四冠环丁烷的rctt异构体。通过X射线衍射证实了双（皇冠）对苯二甲酸酯和所获得的环丁烷的配合物的结构。
• “Two‐Point” Self‐Assembly and Photoinduced Electron Transfer in <i>meso</i> ‐Donor‐Carrying Bis(styryl crown ether)‐BODIPY–Bis(alkylammonium)fullerene Donor–Acceptor Conjugates
  作者：Shuai Shao、Habtom B. Gobeze、Paul A. Karr、Francis D'Souza

  DOI：10.1002/asia.201700662

  日期：2017.9.5

  BODIPY, was functionalized to carry two styryl crown ether tails and a secondary electron donor at the meso position. By using a “two-point” self-assembly strategy, a bis-alkylammonium-functionalized fullerene (C60) was allowed to self-assemble the crown ether voids of BODIPY to obtain multimodular donor–acceptor conjugates. As a consequence of the two-point binding, the 1:1 stoichiometric complexes formed

  BF 2 -chelated二吡咯亚甲基，BODIPY，被官能化以携带两个苯乙烯基冠醚尾巴和在二次电子供体的内消旋位置。通过使用“两点”自组装策略，双烷基铵官能化的富勒烯（C 60）被允许自组装BODIPY的冠醚空洞，以获得多模数的供体-受体结合物。由于两点结合，形成的1：1化学计量的配合物产生了更高稳定性的配合物，其中发现BODIPY的荧光被猝灭了。这暗示了激发态过程的发生。自组装复合物的几何结构和电子结构源自B3LYP / 3-21G（*）方法，其中未观察到实体之间的空间约束。通过使用光谱，电化学和计算结果建立了能级图，以帮助理解源自1的激发态过程的机理细节。bis-styryl-BODIPY *。飞秒瞬态吸收研究表明在电荷分离过程产生双苯乙烯基-BODIPY之前形成了激基复合物状态。+ –C 60 。−自由基离子对。电荷分离的时间常数通常低于电荷复合过程。本研究显示出多模式结合策略对
• Metal-containing ditopic receptors for molecular recognition of diammonium cations
  作者：Olga P Kryatova、Alexander G Kolchinski、Elena V Rybak-Akimova

  DOI：10.1016/s0040-4020(02)01482-5

  日期：2003.1

  Two new ditopic receptors for α,ω-alkanediyldiammonium cations based on a tetraazamacrocyclic (cyclidene) nickel(II) complex bearing two crown-ether residues were synthesized. The studies of the host–guest interaction between the receptors and a series of α,ω-diammonium salts by NMR titration in acetonitrile-d3 showed that 1:1 complexes are formed with Kassoc∼103–105 M−1. Receptor 1 with benzo-15-crown-5

  基于带有两个冠醚残基的四氮杂大环（亚环己基）镍（Ⅱ）配合物，合成了两个新的α，ω-烷二基二铵阳离子的对位受体。受体，并通过NMR一系列α，ω-二铵盐之间的主-客体相互作用的研究滴定乙腈d 3表明，1：1的复合物与形成ķ ASSOC〜10 3 -10 5 中号-1。具有苯并15冠5臂的受体1在结合三亚甲基和四亚甲基二铵离子时显示出显着的选择性，较短的（C 2）或更长的（C 5和C 6）的结合弱1-2个数量级。）二铵阳离子。具有苯并18-冠-6臂的受体2对所有研究的二铵阳离子均显示出较高的亲和力，但对α，ω-二铵阳离子的长度的识别不太明显。
• Supramolecular complexes obtained from porphyrin–crown ether conjugates and a fullerene derivative bearing an ammonium unit
  作者：Nathalie Solladié、Mathieu E. Walther、Haiko Herschbach、Emmanuelle Leize、Alain Van Dorsselaer、Teresa M. Figueira Duarte、Jean-François Nierengarten

  DOI：10.1016/j.tet.2005.07.120

  日期：2006.2

  has been prepared and its ability to form a supramolecular complex with a porphyrin–crown ether conjugate evidenced by NMR, UV–vis, electrospray mass spectrometry (ES-MS) and luminescence experiments. Interestingly, in addition to the ammonium–crown ether recognition, intramolecular stacking of the fullerene moiety and the porphyrin subunit has been evidenced. Due to this additional recognition element

  制备了具有铵亚基（1）的亚甲基富勒烯衍生物，并具有与卟啉-冠醚共轭物形成超分子复合物的能力，这已通过NMR，UV-vis，电喷雾质谱（ES-MS）和发光实验证明。有趣的是，除了铵-冠醚识别外，富勒烯部分和卟啉亚基的分子内堆积也得到了证明。由于这种额外的识别元素，与发现1与苯并18-冠-6络合的K a值相比，超分子络合物的缔合常数增加了两个数量级。最后，由于阳离子1的缔合而产生的非共价体系带有两个冠醚亚基的卟啉衍生物已被研究。在这些超分子复合物中，分子内的C 60-卟啉相互作用也得到了证实。结果，如ES-MS研究所示，2：1配合物非常稳定。