6-溴色烯-2-酮 | 19063-55-9

• 物质功能分类: 有机原料 - 酮类化合物
• 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: 6-溴色烯-2-酮
• 英文名称: 6-bromo-2H-chromen-2-one
• 英文别名: 6-bromocoumarin；6-Bromochromen-2-one
• CAS: 19063-55-9
• 化学式: C₉H₅BrO₂
• 分子量: 225.041
• InChiKey: XXRJDOQENVGLJT-UHFFFAOYSA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  349.2±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)：
  2.1
• 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：
  2932209090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温下应保持干燥和密封存储。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromochromen-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: 6-Bromochromen-2-one
CAS number: 19063-55-9

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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：

  6-溴色烯-2-酮 在 sodium amalgam 、 乙醇 作用下， 生成 6-溴苯并二氢吡喃-2-酮
  参考文献：
  名称：

  Lasch, Monatshefte fur Chemie, 1913, vol. 34, p. 1660

  摘要：

  DOI：
• 作为产物：
  描述：

  氢化肉桂酸内酯 在 溴 作用下， 生成 6-溴色烯-2-酮
  参考文献：
  名称：

  Lasch, Monatshefte fur Chemie, 1913, vol. 34, p. 1660

  摘要：

  DOI：

文献信息

• Process for preparation of benzo[f]quinolinones
  申请人：Eli Lilly and Company

  公开号：US05578724A1

  公开（公告）日：1996-11-26

  A series of benzoquinolin-3-ones are pharmaceuticals effective in treating conditions consequent on both Type I and Type II 5.alpha.-reductase and their preparation is disclosed.

  一系列苯醌啉-3-酮类药物在治疗由I型和II型5α-还原酶引起的疾病方面具有有效性，并且其制备方法已被披露。
• Palladium-Catalyzed Synthesis of Benzofurans and Coumarins from Phenols and Olefins
  作者：Upendra Sharma、Togati Naveen、Arun Maji、Srimanta Manna、Debabrata Maiti

  DOI：10.1002/anie.201305326

  日期：2013.11.25

  Triple CH functionalization: Palladium‐catalyzed synthesis of benzofurans and coumarins by reacting phenols and unactivated olefins is described. The reaction comprises sequential CH functionalization and shows diverse functional group compatibility. Preliminary mechanistic studies shed light into the possible mechanisms.

  三重CH官能化：描述了通过酚与未活化的烯烃反应，钯催化合成苯并呋喃和香豆素。该反应包括顺序的CH官能化，并显示出各种官能团相容性。初步的机理研究阐明了可能的机制。
• Direct conjugate alkylation of α,β-unsaturated carbonyls by Ti^III-catalysed reductive umpolung of simple activated alkenes
  作者：Plamen Bichovski、Thomas M. Haas、Manfred Keller、Jan Streuff

  DOI：10.1039/c5ob02631h

  日期：——

  The titanium(III)-catalysed cross-selective reductive umpolung of Michael-acceptors represents a unique direct conjugate β-alkylation reaction. It allows the cross-selective preparation of 1,6- and 1,4-difunctionalised building blocks without the requirement of stoichiometric organometallic reagents. In this full paper, the development and scope of the titanium(III)-catalysed cross-selective reductive

  钛（III）催化的迈克尔受体的交叉选择性还原活性代表了独特的直接共轭β-烷基化反应。它允许交叉选择制备1,6-和1,4-双官能化的结构单元，而无需化学计量的有机金属试剂。在这篇全文中，描述了钛（III）催化的迈克尔受体交叉选择还原还原活性剂的发展和范围。基于观察到的选择性和其他机械实验，提出了一种完善的机械方案。
• Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions
  作者：Parul Chauhan、Makthala Ravi、Shikha Singh、Prashant Prajapati、Prem P. Yadav

  DOI：10.1039/c5ra20954d

  日期：——

  A transition-metal-free regioselective α-arylation of coumarins and 2-pyridones has been accomplished by the reaction of phenylhydrazines with coumarins or 2-pyridones.

  一种无过渡金属的选择性α-芳基化反应已经成功实现，通过苯基肼与香豆素或2-吡啶酮的反应。
• Structure−Activity Relationship and Molecular Mechanisms of Ethyl 2-Amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4<i>H</i>-chromene-3-carboxylate (sHA 14-1) and Its Analogues
  作者：Sonia G. Das、Jignesh M. Doshi、Defeng Tian、Sadiya N. Addo、Balasubramanian Srinivasan、David L. Hermanson、Chengguo Xing

  DOI：10.1021/jm9005059

  日期：2009.10.8

  excitingly, our studies of 5q in camptothecin (CCRF-CEM/C2) and mitoxantrone (HL-60/MX2) resistant cancer cells highlight its ability to selectively kill drug-resistant cells over parent cancer cells. 5q inhibits tumor cell growth through the induction of apoptosis, with detailed mechanism of its selectivity toward drug-resistant cancer cells under investigation. These results suggest that 5q is a promising

  对当前疗法的多种耐药性的快速发展是癌症治疗中的主要障碍。因此，可以克服癌细胞中获得的耐药性的抗癌剂非常重要。以前，我们已经证明2-氨基-4-（2-乙氧基-2-氧代乙基）-6-苯基-4 H-苯甲基-3-羧酸乙酯（5a，sHA 14-1）是乙基2的稳定类似物-氨基-6-溴-4-（1-氰基-2-乙氧基-2-氧代乙基）-4 H-苯甲基-3-羧酸盐（6，HA 14-1），减轻耐药性并与多种癌症协同作用白血病细胞的疗法。5a的结构活性关系（SAR）研究指导了乙基2-氨基-6-（3'，5'-二甲氧基苯基）-4-（2-乙氧基-2-氧代乙基）-4的发展H - chromene -3-carboxylate（5q，CXL017），一种对多种血液学和实体瘤细胞具有低微摩尔细胞毒性的化合物。更令人兴奋的是，我们对喜树碱（CCRF-CEM / C2）和米托蒽醌（HL-60 / MX2）耐药癌细胞中的5q的研究突显了