8-溴-2H-1-苯并吡喃-2-酮 | 33491-30-4

• 物质功能分类: 医药中间体 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 8-溴-2H-1-苯并吡喃-2-酮
• 英文名称: 8-bromocoumarin
• 英文别名: 8-bromo-2H-chromen-2-one；8-Bromo-2H-1-benzopyran-2-one；8-bromochromen-2-one
• CAS: 33491-30-4
• 化学式: C₉H₅BrO₂
• 分子量: 225.041
• InChiKey: BIVMXYHSBRLPDE-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C(Solv: methanol (67-56-1))
• 沸点：
  352.2±37.0 °C(Predicted)
• 密度：
  1.688±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 8-Bromo-2h-1-benzopyran-2-one
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 8-Bromo-2h-1-benzopyran-2-one
CAS number: 33491-30-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H5BrO2
Molecular weight: 225.0

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  8-溴-2H-1-苯并吡喃-2-酮 在 硫酸 、 硝酸 作用下， 以 水 为溶剂， 反应 0.5h， 以83%的产率得到8-溴-6-硝基-2H-色烯-2-酮
  参考文献：
  名称：

  开发具有令人满意的荧光特性和显着大斯托克斯位移的新型吡咯香豆素衍生物

  摘要：

  具有大斯托克斯位移和长发射波长的小型有机荧光分子是各种现代荧光成像技术（如 FRET）的理想染料。在这项研究中，我们在两个吡咯香豆素骨架的基本结构上设计并合成了许多新的荧光分子，其中 Fischer 的吲哚合成和 Suzuki 偶联成功地作为有效的分子编辑方案。对这些化合物的荧光特性和进一步结构优化的检查提供了三种具有显着大斯托克斯位移和令人满意的荧光特性的新型吡咯并香豆素染料。其中，30 表现出较大的斯托克斯位移（113 nm）和强烈的荧光（φ = 0.55，λem = 523 nm），因此在生物成像研究中显示出巨大的潜力。(© Wiley-VCH Verlag GmbH & Co.

  DOI：

  10.1002/ejoc.200800883
• 作为产物：
  描述：

  2-溴苯酚 在 potassium acetate 、 三乙胺 、 magnesium chloride 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 8-溴-2H-1-苯并吡喃-2-酮
  参考文献：
  名称：

  香豆素基环化金属的Ir（III）配合物的异构体，具有容易调节的磷光颜色和高效有机发光二极管的特性

  摘要：

  三个红外（C ∧ N）2（ACAC）型和一个IR（C 1 ∧ N）（C 2 ∧ N）（ACAC）型香豆素系环金属化铱（III）配合物的异构体（IRC5，IrC7，IrC7- A和IrC8已使用2-苯基吡啶（ppy）型环金属化配体的三个香豆素基异构体（L-C5，L-C7和L-C8）获得。两种配位异构体成为主要产物（IrC7和IrC7-A）是在相应的香豆素基环金属化Ir（III）配合物的合成中获得的，因为配体L-C7中两个不同的配位点形成了C-Ir键。据我们所知，迄今尚无此类异构体的报道。有趣的是，通过改变香豆素骨架的稠合苯环上的吡啶基取代位置，已经实现了从绿色（IrC8，λ= 516 nm）到红色（IrC5，λ= 608 nm）的磷光色调节。此外，基于自然跃迁轨道（NTO）分析，这些基于香豆素的环金属化Ir（III）复杂异构体的最低三重态激发态（T 1）的特征也可以通过这些配体异构体轻松调整

  DOI：

  10.1021/acs.inorgchem.9b00534

文献信息

• Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2<i>H</i>-Chromenes
  作者：Aymeric Cervi、Yen Vo、Christina L. L. Chai、Martin G. Banwell、Ping Lan、Anthony C. Willis

  DOI：10.1021/acs.joc.0c02011

  日期：2021.1.1

  Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal

  报道了有效组装一系列由苯酚衍生的丙酸酯的方法，包括母体系统56，以及它们的Au（I）催化的环化（分子内氢芳基化），得到相应的香豆素（例如1）。通过这样的方法已经实现了天然产物例如ayapin（144）和scoparone（145）的简单合成，并且首先对它们进行单晶X射线分析。描述了一种用于将诸如156的炔丙基醚转化为天然存在的少年激素生物合成抑制剂的异构体2 H-苯并二茂烯I（159）的方法。
• Metal-free regioselective C–H chalcogenylation of coumarins/(hetero)arenes at ambient temperature
  作者：Zengqiang Song、Chaochao Ding、Shaoli Wang、Qian Dai、Yaoguang Sheng、Zhilong Zheng、Guang Liang

  DOI：10.1039/c9cc09001k

  日期：——

  A novel, practical and metal-free approach for the regioselective selenation of coumarins employing (bis(trifluoroacetoxy)iodo)benzene (PIFA) at room temperature is presented. The developed method is suitable for a wide substrate scope and affords 3-selenyl coumarins in good to excellent yields with high selectivity. A radical mechanism is proposed for this new transformation. Furthermore, the application

  提出了一种新颖，实用且无金属的室温下使用（双（三氟乙酰氧基）碘）苯（PIFA）的香豆素区域选择性硒化方法。所开发的方法适用于广泛的底物范围，并以高至优异的产率和高选择性提供了3-硒基香豆素。为这种新的转变提出了一种激进的机制。此外，在该转化中成功应用了香豆素的亚磺酰化和其他（杂）芳烃的硒化。
• Derivatization of Coumarins at the Benzenoid Ring in Aqueous Medium
  作者：Sankar C Bhunia、Sutanuka Pal、Gopal C Patra、Sudhir C Pal

  DOI：10.1002/jhet.1800

  日期：2014.11

  prepared from coumarin, 7‐methylcoumarin, and 3,4‐benzocoumarin. The Reimer–Tiemann reaction, Lederer–Manasse reaction, bromination using molecular bromine as well as 2,4,4,6‐tetrabromocyclohex‐2,5‐dien‐1‐one, Elbs reaction, and diazocoupling have been carried under controlled conditions to obtain various derivatives. Further, several reactions of aldehyde derivatives of these coumarins have been carried

  从香豆素，7-甲基香豆素和3,4-苯并香豆素制备了一些6-二取代，8-二取代和/ 6,8-二取代的化合物。Reimer–Tiemann反应，Lederer–Manasse反应，使用分子溴以及2,4,4,6-四溴环己基-2,5-dien-1的溴化，Elbs反应和重氮偶联已在受控条件下进行。获得各种衍生物。此外，已经进行了这些香豆素的醛衍生物的几次反应以制备重要的功能化合物，包括一些杂环。值得注意的是，这些醛在碱性条件下表现为酚醛，从而发生Dakin反应。反应主要在涉及双阴离子中间体的水性介质中进行，因此符合绿色化学的一项重要标准。
• Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent. II : Synthesis ofBromo- and Methoxycarbonylcoumarins.
  作者：Takashi HARAYAMA、Kazumitsu NAKATSUKA、Hiromi NISHIOKA、Kyoko MURAKAMI、Naomi HAYASHIDA、Hisashi ISHII

  DOI：10.1248/cpb.42.2170

  日期：——

  Reaction of salicylaldehydes (1) with carbethoxymethylenetriphenylphosphorane in diethylaniline under reflux gave coumarins (3) in moderate to high yield except 3-methoxycarbonylsalicyladehyde (1e) as summarized in Table I. The substituent effects are discussed. A substituent at C6 on 1 usually facilitated the formation of the coumarin ring regardless of its electronic character.

  在二乙基苯胺中，加热回流下香兰素（1）与碳乙氧基亚甲基三苯基磷烯反应，除了3-甲氧基羧基香兰素（1e）外，得到了中等到高产率的香豆素（3），具体结果总结在表I中。讨论了取代基的影响。在1的C6位的取代基通常促进香豆素环的形成，无论其电子特性如何。
• Construction of a CF₃-Containing Benzofurofuranone Skeleton from Coumarins via Reductive Coupling and Acid-Mediated Ring Contraction
  作者：Tianyuan Zhang、Yuhei Shimizu、Shuhei Fukaya、Tomofumi Sawa、Hirofumi Maekawa

  DOI：10.1021/acs.joc.9b01439

  日期：2019.9.20

  trifluoroacetyl group to coumarin in the presence of ethyl trifluoroacetate and the subsequent treatment with trifluoroacetic acid led to simple access to a trifluoromethylated benzofurofuranone at 8a-position with a high regio- and stereoselectivity. Trifluoromethylated or difluoromethylated benzofurofuranone derivatives were also prepared from coumarins including naturally occurring ones only in two successive

  在三氟乙酸乙酯存在下，镁促进的三氟乙酰基向香豆素的还原性引入以及随后用三氟乙酸的处理导致在8a-位简单地获得具有高区域和立体选择性的三氟甲基化苯并呋喃呋喃酮。三氟甲基化或二氟甲基化的苯并呋喃呋喃酮衍生物也仅在两个连续的步骤中由香豆素制备而成，包括天然存在的香豆素，在药物化学中可能具有潜在的生物活性。