5-氯-2,3,3-三甲基吲哚 | 25981-83-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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-氯-2,3,3-三甲基吲哚
• 中文别名: 2,3,3-三甲基-5-氯-3H-吲哚；2,2-亚甲基双[6-(1-苯基乙基)-4-甲酚]
• 英文名称: 5-chloro-2,3,3-trimethyl-3H-indole
• 英文别名: 5-chloro-2,3,3-trimethylindole；5-chloro-2,3,3-trimethylindolenine
• CAS: 25981-83-3
• 化学式: C₁₁H₁₂ClN
• mdl: MFCD00126966
• 分子量: 193.676
• InChiKey: GSKATGIMEUGNJN-UHFFFAOYSA-N

物化性质

• 沸点：
  271.1±40.0 °C(Predicted)
• 密度：
  1.083 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Chloro-2,3,3-trimethyl-3H-indole
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: 5-Chloro-2,3,3-trimethyl-3H-indole
CAS number: 25981-83-3

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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, refrigerated.
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: C11H12ClN
Molecular weight: 193.7

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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 chloride.

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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：

  5-氯-2,3,3-三甲基吲哚 在 sodium hydroxide 作用下， 以 氯仿 、 三氯乙烯 为溶剂， 反应 3.5h， 生成 6-(Azepan-1-yl)-5'-chloro-1',3',3'-trimethylspiro[benzo[f][1,4]benzoxazine-3,2'-indole]
  参考文献：
  名称：

  Synthesis, characterization and photochromic studies in film of heterocycle-containing spirooxazines

  摘要：

  A series of novel heterocycle-containing spirooxazines have been designed and synthesized, and their photochromic properties were investigated under flash photolysis and continuous irradiation in particular regard to the fatigue resistance, the lifetime of the colored merocyanine form in various solutions and polymers. Especially, the characteristics of two UV-sensitive spirooxazines dispersed polymethylmethacrylate thin-films were extensively studied. Detailed studies showed that general significant shifts in the lambda(max) of the absorption spectra of the open forms, interesting fatigue resistances and emission fluorescene properties were observed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.057
• 作为产物：
  描述：

  4,4-二甲基-5-亚甲基-1,3-二氧戊环-2-酮 在 zinc(II) chloride 作用下， 以 paraffin 、 xylene 为溶剂， 反应 20.0h， 生成 5-氯-2,3,3-三甲基吲哚
  参考文献：
  名称：

  Eine einfache Synthese von 3H-Indolen ausgehend von acetylenischen Alkoholen

  摘要：

  DOI：

  10.1055/s-1981-29655

文献信息

• YELLOW METHINE DYES
  申请人：LANXESS Deutschland GmbH

  公开号：US20170349752A1

  公开（公告）日：2017-12-07

  The present invention relates to novel methine dyes, methods for the preparation thereof and use thereof for dyeing plastics, especially polyamides, so as to obtain yellow colorings with improved light fastness and improved thermostability.

  本发明涉及新型甲纶染料，其制备方法以及用于染色塑料，特别是聚酰胺，以获得具有改善的耐光性和改善的热稳定性的黄色染料。
• NOVEL METHINE DYES
  申请人：LANXESS Deutschland GmbH

  公开号：US20190161618A1

  公开（公告）日：2019-05-30

  Novel red methine dyes, methods for the preparation thereof, and use thereof for dyeing plastics, especially vinyl polymers, provide red colourings with improved colour strengths and improved colour brilliance.

  新型红色甲纶染料，其制备方法以及用于染色塑料，特别是乙烯聚合物的用途，提供了具有改善的色彩强度和色彩光泽的红色着色剂。
• Carbocyanines for G-Quadruplex DNA Stabilization and Telomerase Inhibition
  申请人：Henary Maged

  公开号：US20140142147A1

  公开（公告）日：2014-05-22

  Cyanines which selectively bind to G-quadruplex DNA complexes, particularly quadruplexes expressed in cancer cells, and methods of making and using thereof are described herein. The cyanine can be a symmetrical or unsymmetrical streptocyanine, hemicyanine, closed chain cyanine, or combinations thereof. The cyanine is preferably substituted with one or more groups that minimize or prevent aggregation of the cyanine and/or inhibit binding of the cyanine to duplex DNA. One or more of the cyanines can be formulated with one or more pharmaceutical excipients and/or carrier to prepare pharmaceutical compositions suitable for administration to a patient, particular a human patient. The compounds and compositions described herein can be used to treat diseases or disorders characterized by the expression of G-quadruplex DNA, such as cancer.

  本文描述了选择性结合到G-四链体DNA复合物的青菁类化合物，特别是在癌细胞中表达的四链体，以及其制备和使用方法。该青菁类化合物可以是对称或非对称的链青菁、半青菁、闭环青菁，或其组合。该青菁类化合物最好被取代为一个或多个基团，以最小化或防止青菁类化合物的聚集和/或抑制其与双链DNA的结合。其中一个或多个青菁类化合物可以与一个或多个药用辅料和/或载体配制，以制备适合用于患者，特别是人类患者的药物组合物。本文描述的化合物和组合物可用于治疗由G-四链体DNA表达特征的疾病或紊乱，如癌症。
• Selective G-Quadruplex DNA Recognition by a New Class of Designed Cyanines
  作者：Rupesh Nanjunda、Eric Owens、Leah Mickelson、Tyler Dost、Ekaterina Stroeva、Hang Huynh、Markus Germann、Maged Henary、W. Wilson

  DOI：10.3390/molecules181113588

  日期：——

  A variety of cyanines provide versatile and sensitive agents acting as DNA stains and sensors and have been structurally modified to bind in the DNA minor groove in a sequence dependent manner. Similarly, we are developing a new set of cyanines that have been designed to achieve highly selective binding to DNA G-quadruplexes with much weaker binding to DNA duplexes. A systematic set of structurally analogous trimethine cyanines has been synthesized and evaluated for quadruplex targeting. The results reveal that elevated quadruplex binding and specificity are highly sensitive to the polymethine chain length, heterocyclic structure and intrinsic charge of the compound. Biophysical experiments show that the compounds display significant selectivity for quadruplex binding with a higher preference for parallel stranded quadruplexes, such as cMYC. NMR studies revealed the primary binding through an end-stacking mode and SPR studies showed the strongest compounds have primary KD values below 100 nM that are nearly 100-fold weaker for duplexes. The high selectivity of these newly designed trimethine cyanines for quadruplexes as well as their ability to discriminate between different quadruplexes are extremely promising features to develop them as novel probes for targeting quadruplexes in vivo.

  多种菁染料作为DNA染料和传感器具有多功能性和灵敏性，并已通过结构修饰，以序列依赖的方式结合于DNA小沟。同样，我们正在开发一套新的菁染料，这些染料被设计用于高度选择性地结合DNA G-四链体，而对DNA双链的结合力较弱。系统地合成了结构类似的三甲川菁染料并评估了其对四链体的靶向作用。结果显示，增强四链体结合和特异性对多甲川链长度、杂环结构和化合物的固有电荷非常敏感。生物物理实验表明，这些化合物对四链体结合表现出显著的选择性，更偏好于平行链四链体，如cMYC。核磁共振研究揭示了主要通过末端堆积模式结合，表面等离子体共振研究显示最强的化合物主要的解离常数值低于100 nM，而对双链体的结合力几乎弱了100倍。这些新设计的三甲川菁染料对四链体的高度选择性以及它们区分不同四链体的能力是非常有前景的特性，有望开发它们作为体内靶向四链体的新型探针。
• Ring transformations of heterocyclic compounds.<b>XXII</b>. Pyrido[1,2-<i>a</i>]indolium salts from 2-methyl-3<i>H</i>-indoles by pyrylium mediated three carbon annelation
  作者：Thomas Zimmermann、Lothar Hennig

  DOI：10.1002/jhet.5570390203

  日期：2002.3

  The synthesis of pyrido[1,2-a]indolium perchlorates 8,11 from 2,4,6-triarylpyrylium perchlorates 1 and 2-methyl-3H-indoles 6,9 in the presence of a basic condensing agent (anhydrous sodium acetate, piperidine acetate, triethylamine/acetic acid, triethylamine) in ethanol by a 2,4-[C3+C2N] pyrylium ring transformation is reported. Spectroscopic data of the transformation products and their mode of formation

  吡啶并合成[1,2一]吲哚鎓高氯酸盐-8,11-从2,4,6-三芳基高氯酸盐1和2-甲基-3- ħ -indoles 6,9在碱性缩合剂的存在下（无水醋酸钠报道了乙醇中乙酸哌啶，三乙胺/乙酸，三乙胺通过2，4- [C 3 + C 2 N]吡啶鎓环的转化。讨论了转化产物的光谱数据及其形成方式。