5-溴-1-甲基-2-氧吲哚烷 | 20870-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-溴-1-甲基-2-氧吲哚烷
• 中文别名: 5-溴-1-甲基-2-吲哚酮
• 英文名称: 5-bromo-1-methyl-1,3-dihydro-indol-2-one
• 英文别名: 5-bromo-1-methylindolin-2-one；5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one；5-Brom-N-methyl-oxindol；5-Bromo-1-methyl-2-oxoindoline；5-bromo-1-methyl-3H-indol-2-one
• CAS: 20870-90-0
• 化学式: C₉H₈BrNO
• mdl: MFCD00464061
• 分子量: 226.073
• InChiKey: WARSUKBSFLACOI-UHFFFAOYSA-N

物化性质

• 熔点：
  132 °C
• 沸点：
  418.1±45.0 °C(Predicted)
• 密度：
  1.589±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933790090
• 包装等级：
  III
• 危险类别：
  8,6.1
• 危险性防范说明：
  P261,P280,P301+P310,P305+P351+P338
• 危险品运输编号：
  2923
• 危险性描述：
  H301,H315,H318,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
5-Bromo-1-methyl-2-oxoindoline
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
5-Bromo-1-methyl-2-oxoindoline
Ingredient name:
CAS number: 20870-90-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H8BrNO
Molecular weight: 226.1

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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, nitrogen oxides, 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
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (5-Bromo-1-methyl-2-oxoindoline)

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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：

  5-溴-1-甲基-2-氧吲哚烷 在 亚硝酸特丁酯 、 氧气 作用下， 以 四氢呋喃 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以62%的产率得到5-溴-1-甲基-1H-吲哚-2,3-二酮
  参考文献：
  名称：

  氧化吲哚的无金属氧化方便、清洁合成靛红

  摘要：

  在作为添加剂的亚硝酸叔丁酯存在下，通过羟吲哚与分子氧的氧化反应，实现了靛红的无金属合成。该策略为构建 C=O 键提供了一种方便且简单的合成途径，无需任何催化剂或碱。该反应的吸引人的特点包括其方便的程序和温和的反应条件。

  DOI：

  10.1055/s-0036-1590965
• 作为产物：
  描述：

  5-溴-1-甲基-1H-吲哚-2,3-二酮 在 一水合肼 作用下， 反应 1.0h， 生成 5-溴-1-甲基-2-氧吲哚烷
  参考文献：
  名称：

  金鸡纳生物碱催化的3-氟羟吲哚与多聚甲醛的对映选择性羟甲基化

  摘要：

  使用多聚甲醛作为C1单元，实现了金鸡纳生物碱催化的3-氟代吲哚的羟甲基化反应。各种各样的3-氟代羟吲哚成功地反应生成了相应的3-氟-3-羟甲基羟甲基吲哚，具有高效率和中等至良好的对映选择性。

  DOI：

  10.1016/j.jfluchem.2018.09.004
• 作为试剂：
  描述：

  5-溴-1-甲基-2-氧吲哚烷 、 在 5-溴-1-甲基-2-氧吲哚烷 作用下， 以31的产率得到5-[4-(4-hydroxy-2-methyloxan-4-yl)thiophen-2-yl]sulfanyl-1-methyl-3H-indol-2-one
  参考文献：
  名称：

  Org. Process Res. Dev. 1997, 1, 61-67

  摘要：

  DOI：

文献信息

• Autoxidation/Aldol Tandem Reaction of 2-Oxindoles with Ketones: A Green Approach for the Synthesis of 3-Hydroxy-2-Oxindoles
  作者：Qing-Bao Zhang、Wen-Liang Jia、Yong-Liang Ban、Yong Zheng、Qiang Liu、Li-Zhu Wu

  DOI：10.1002/chem.201504282

  日期：2016.2.18

  In the presence of tetrabutylammonium fluoride and molecular sieves (MS) 4 Å in DMF, an efficient autoxidation reaction of 2‐oxindoles with ketones under air at room temperature has been developed. This approach may provide a green, practical, and metal‐free protocol for a wide range of biologically important 3‐hydroxy‐3‐(2‐oxo‐alkyl)‐2‐oxindoles.

  在DMF中存在四丁基氟化铵和分子筛（MS）4Å的情况下，已开发出室温下空气中2-氧吲哚与酮的有效自氧化反应。这种方法可能为多种生物学上重要的3-羟基-3-（2-氧代烷基）-2-氧吲哚提供绿色，实用且不含金属的方案。
• Acylation of oxindoles using methyl/phenyl esters <i>via</i> the mixed Claisen condensation – an access to 3-alkylideneoxindoles
  作者：Ramdas Sreedharan、Purushothaman Rajeshwaran、Pradeep Kumar Reddy Panyam、Saurabh Yadav、C. M. Nagaraja、Thirumanavelan Gandhi

  DOI：10.1039/d0ob00789g

  日期：——

  Predominantly, aggressive acid chlorides and stoichiometric coupling reagents are employed in the acylating process for synthesizing carbonyl tethered heterocycles. Herein, we report simple acyl sources, viz. methyl and phenyl esters, which acylate oxindoles via the mixed Claisen condensation. This straightforward protocol is mediated by LiHMDS and KOtBu and successfully applied to a wide range of

  在酰化过程中，主要使用侵蚀性的酰氯和化学计量的偶联剂来合成羰基束缚的杂环。在这里，我们报告简单的酰基来源，即。甲酯和苯酯，它们通过混合的克莱森缩合反应酰化吲哚。这种简单的方法是由LiHMDS和KOtBu介导的，并成功地应用于各种基材。这是一个值得注意的转变，它跳过了烯醇化物和酰化的逐步生成，并且该反应在中等温度下进行，没有任何副反应。该方案产生了芳基环中的邻位取代基的第一个例子，该芳基环上有供电子和吸电子底物。有趣的是，坚固的有机金属二茂铁基甲基酯在这些条件下容易裂解。此外，
• IMIDAZOPYRAZINES AS LSD1 INHIBITORS
  申请人：Incyte Corporation

  公开号：US20160009720A1

  公开（公告）日：2016-01-14

  The present invention is directed to imidazo[1,2-a]pyrazine derivatives which are LSD1 inhibitors useful in the treatment of diseases such as cancer.

  本发明涉及咪唑并[1,2-a]吡嗪衍生物，这些衍生物是LSD1抑制剂，可用于治疗癌症等疾病。
• Transition-metal-free Chemoselective Oxidative C−C Coupling of the sp³C−H Bond of Oxindoles with Arenes and Addition to Alkene: Synthesis of 3-Aryl Oxindoles, and Benzofuro- and Indoloindoles
  作者：Moh. Sattar、Vandana Rathore、Ch. Durga Prasad、Sangit Kumar

  DOI：10.1002/asia.201601647

  日期：2017.4.4

  A transition‐metal (TM)‐free and halogen‐free NaOtBu‐mediated oxidative cross‐coupling between the sp3 C−H bond of oxindoles and sp2 C−H bond of nitroarenes has been developed to access 3‐aryl substituted and 3,3‐aryldisubstituted oxindoles in DMSO at room temperature in a short time. Interestingly, the sp3 C−H bond of oxindoles could also react with styrene under TM‐free conditions for the practical

  过渡金属（TM）-free和无卤素的NaO吨卜介导的氧化的SP之间的交叉耦合3羟吲哚和SP的C-H键2硝基芳烃的C-H键已经发展到接入3-芳基取代的室温下，短时间内在DMSO中有3,3-芳基二取代的羟吲哚。有趣的是，在没有TM的条件下，羟吲哚的sp 3 C-H键也可以与苯乙烯反应，用于实际合成季铵3,3-二取代的羟吲哚。合成的3-氧吲哚也进一步转化为高级杂环，即苯并呋喃吲哚，吲哚吲哚和取代的吲哚。反应的机理实验表明，由sp 3形成阴离子中间体在DMSO中由叔丁醇碱形成的羟吲哚的CH键。在原位产生的碳负离子中添加硝基苯会导致DMSO中的3-（硝基苯基）氧杂吲哚基碳负离子，随后被DMSO氧化为3-（硝基-芳基）羟吲哚。
• [EN] PYRIDINONE DERIVATIVES AND THEIR USE AS SELECTIVE ALK-2 INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDINONE ET LEUR UTILISATION EN TANT QU'INHIBITEURS SÉLECTIFS D'ALK-2
  申请人：NOVARTIS AG

  公开号：WO2019102256A1

  公开（公告）日：2019-05-31

  The invention relates to a compound of Formula I or a pharmaceutically acceptable salt thereof, a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  该发明涉及公式I的化合物或其药用可接受盐，以及制造该发明化合物的方法及其治疗用途。本发明还提供了药理活性剂的组合和药物组成。