4-溴[2.2]对环芳烷 | 1908-61-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 4-溴[2.2]对环芳烷
• 英文名称: 4-bromo[2.2]paracyclophane
• 英文别名: (rac)-4-bromo[2.2]paracyclophane；1²-bromo-1,4(1,4)-dibenzenacyclohexaphane；5-bromotricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaene
• CAS: 1908-61-8
• 化学式: C₁₆H₁₅Br
• mdl: MFCD00187358
• 分子量: 287.199
• InChiKey: RJOYWTPJYZNRJD-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  370.5±31.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放在阴凉干燥处即可。

SDS

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Section 1: Product Identification
Chemical Name: racemic-4-Bromo[2.2]paracyclophane, min. 95%
CAS Registry Number: 1908-61-8
Formula: C16H15Br
EINECS Number: none
Chemical Family: organic bromide
Synonym: 5-Bromotricyclo[8,2,2,24,7]hexadeca-4,6,10,12,13,15-hexaene

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 1908-61-8 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No specific information is available on the physiological effects of ingestion.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unususal fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Store in a tightly sealed container. Keep in a cool, dry, well ventilated place.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white powder
Molecular Weight: 287.19
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: strong oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide, organic fumes, hydrogen bromide

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Title compound not listed
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

用作化学试剂。

用途简介

暂无描述。

用途

用作化学试剂。

反应信息

• 作为反应物：
  描述：

  4-溴[2.2]对环芳烷 在 盐酸 、 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 生成 4,15-dibromo[2.2]paracyclophane
  参考文献：
  名称：

  Macro rings. XLI. Preparation and reactions of [2.2]metaparacyclophane

  摘要：

  DOI：

  10.1021/ja00748a016
• 作为产物：
  描述：

  4-bromoacetyl<2,2>-para-cyclophane 在 sodium tetrahydroborate 、 水 作用下， 以 乙醇 为溶剂， 以62%的产率得到4-溴[2.2]对环芳烷
  参考文献：
  名称：

  [2,2]-对环芳烷衍生物的合成、结构和生物活性。2. 4-Hydroxymethyl(acyloxymethyl, alkenyl)-[2,3]-para-cyclophanes

  摘要：

  为了研究 [2,2]-对环烷 (PCP) 系列 (I) 新化合物的结构和生物活性，我们基于其 4-酰基衍生物 (II) 合成了 4-羟甲基-、4 -酰氧基甲基-和4-烯基取代的对环芳烃(III-VII)。如 [4] 中获得起始 4-乙酰基 PCP (IIa)。我们通过在二氯甲烷中在-35°的AlCl 3 存在下用苯甲酰氯对PCP I进行苯甲酰化以良好的收率（70％）合成了4-苯甲酰PCP（IIb）。早先的 [5] 中，化合物 1b 是通过 4-PCP 羧酸（= 50% 产率）分四步获得的。基于酮IIa，我们获得了三种新的亚胺：缩氨基脲、缩氨基硫脲和2,4-二硝基苯腙（分别为IIIa-c；化合物的特征和PMR光谱见表1和表2）。通过硼氢化钠还原酮 II，我们获得了甲基 (IVa) 和苯基 (IVb) {[2,2]-对环芳烷-4-基}甲醇，具有不对称中心和单取代对环芳烃部分的不对称平面. 根据

  DOI：

  10.1007/bf02219000

文献信息

• Planar‐Chiral [2.2]Paracyclophane‐Based Pyridonates as Ligands for Tantalum‐Catalyzed Hydroaminoalkylation
  作者：Carolin Braun、Martin Nieger、Stefan Bräse、Laurel L. Schafer

  DOI：10.1002/cctc.201900416

  日期：2019.11.7

  By using planar chiral [2.2]paracyclophane‐containing N,O‐chelating ligands for tantalum‐catalyzed hydroaminoalkylation, one of the most versatile catalytic systems for this reaction to date was obtained. Convenient Csp3−Csp3 bond formation of amines with terminal and internal alkenes was enabled by the same in situ synthesized catalytic system of [2.2]paracyclophane‐based pyridonates and Ta(CH2TMS)3Cl2

  通过使用平面手性[2.2]对环环烷含N，O螯合的配体进行钽催化的氢氨基烷基化反应，获得了迄今为止该反应最通用的催化体系之一。胺与末端和内部烯烃的便捷C sp3 -C sp3键形成是通过相同的原位合成的[2.2]对环环烷基吡啶酸酯和Ta（CH 2 TMS）3 Cl 2催化体系实现的，该结果也显示了非常有希望的结果。ñ含杂环。
• A highly stable, Au/Ru heterobimetallic photoredox catalyst with a [2.2]paracyclophane backbone
  作者：Daniel M. Knoll、Christoph Zippel、Zahid Hassan、Martin Nieger、Patrick Weis、Manfred M. Kappes、Stefan Bräse

  DOI：10.1039/c9dt04366g

  日期：——

  We report the synthesis and catalytic application of a highly stable distance-defined Au/Ru heterobimetallic complex. [2.2]Paracyclophane serves as a backbone, holding the two metal centers in a spatial orientation and metal–metal fixed distance. The Au/Ru heterobimetallic complex is highly stable, easily accessible and exhibits promising catalytic activity in a visible-light mediated dual Au/Ru Meyer–Schuster

  我们报告了高度稳定的距离定义金/钌异双金属配合物的合成和催化应用。[2.2] Paracyclophane是一个骨架，将两个金属中心保持在空间方向，金属与金属之间的距离固定。Au / Ru异双金属配合物非常稳定，易于获得，并且在可见光介导的Au / Ru Meyer-Schuster双重排中表现出有希望的催化活性。
• [EN] [2-2]PARACYCLOPHANE-DERIVED DONOR/ACCEPTOR-TYPE MOLECULES FOR OLED APPLICATIONS<br/>[FR] MOLÉCULES DE TYPE DONNEUR/ACCEPTEUR DÉRIVÉES DE [2-2] PARACYCLOPHANE POUR APPLICATIONS OLED
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2016196885A1

  公开（公告）日：2016-12-08

  Disclosed are [2.2]paracyclophane-derivative compounds and related polymers that are useful as stable, efficient, blue-light emitting compounds for OLED applications.

  揭示了作为OLED应用中稳定、高效、蓝光发射化合物的[2.2]对联环衍生物化合物及相关聚合物。
• Palladium-Catalyzed N-Arylation Reactions with Aziridine and Azetidine
  作者：Bernhard Witulski、Stefan Senft、Jordi Bonet、Oliver Jost

  DOI：10.1055/s-2006-958947

  日期：2007.1

  Studies on the viability of palladium-catalyzed cross-coupling reactions of aryl- or hetaryl bromides with the parent aziridine or azetidine showed that a wide range of N-arylaziridines and N-arylazetidines are accessible by this method. Ring cleavage of the N-arylaziridines or -azetidines thus produced does not occur under the applied reaction conditions. The synthetic utility of the method is illustrated

  对钯催化的芳基溴或杂芳基溴与母体氮丙啶或氮杂环丁烷的交叉偶联反应的可行性研究表明，通过这种方法可以获得范围广泛的 N-芳基氮杂环丙烷和 N-芳基氮杂环丁烷。这样产生的N-芳基氮杂环丙烷或-氮杂环丁烷的开环在所应用的反应条件下不会发生。该方法的合成效用通过使用氮丙啶或氮杂环丁烷的双 N-芳基化的例子来说明。
• 环芳基铱络化合物及使用该化合物的有机电 致发光装置
  申请人：机光科技股份有限公司

  公开号：CN107722059B

  公开（公告）日：2020-05-22

  本发明公开了一种环芳基铱络合物及使用该环芳基铱络合物作为发光层的发光掺杂剂的磷光有机电致发光(有机EL)装置，该装置具有良好的性能表现，如较低驱动电压、功耗及增加的效率及寿命。另外，本发明还公开了合适的发光主体化合物，以与环芳基铱络合物的能量级配合用于本发明。