5-溴-1H-吲唑-1-甲酸叔丁酯 | 651780-02-8

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 5-溴-1H-吲唑-1-甲酸叔丁酯
• 中文别名: 5-溴-1H-吲唑-1-羧酸叔丁酯；5-溴-吲唑-1-羧酸叔丁酯；1-Boc-5-溴吲唑
• 英文名称: tert-butyl 5-bromo-1H-indazole-1-carboxylate
• 英文别名: tert-butyl 5-bromoindazole-1-carboxylate
• CAS: 651780-02-8
• 化学式: C₁₂H₁₃BrN₂O₂
• 分子量: 297.151
• InChiKey: CAQGDWLRIQCXSP-UHFFFAOYSA-N

物化性质

• 沸点：
  377℃
• 密度：
  1.46
• 闪点：
  182℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: tert-Butyl 5-bromo-1h-indazole-1-carboxylate
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: tert-Butyl 5-bromo-1h-indazole-1-carboxylate
CAS number: 651780-02-8

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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: C12H13BrN2O2
Molecular weight: 297.1

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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
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-溴-1H-吲唑-1-甲酸叔丁酯 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 盐酸羟胺 、 chloroamine-T 、 铜 、 copper(II) sulfate 、 三乙胺 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 5-(1H-indazol-5-yl)-N-methylisoxazole-3-carboxamide
  参考文献：
  名称：

  Scaffold oriented synthesis. Part 3: Design, synthesis and biological evaluation of novel 5-substituted indazoles as potent and selective kinase inhibitors employing [2+3] cycloadditions

  摘要：

  We report the synthesis and biological evaluation of 5-substituted indazoles and amino indazoles as kinase inhibitors. The compounds were synthesized in a parallel synthesis fashion from readily available starting materials employing [2+3] cycloaddition reactions and were evaluated against a panel of kinase assays. Potent inhibitors were identified for numerous kinases such as Rock2, Gsk3 beta, Aurora2 and Jak2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.007
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 5-溴吲唑 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以89.5%的产率得到5-溴-1H-吲唑-1-甲酸叔丁酯
  参考文献：
  名称：

  叔丁基-5-(4,4,5,5-四甲基-1,3,2-DIOXABOROLAN-2-YL)-1H-INDAZOLE-1-CARBOXYLATE 的合成、晶体结构和 DFT 研究

  摘要：

  摘要 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1 H -indazole-1-carboxylate叔丁基-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1 H -indazole-1-carboxylate 是1H-吲唑衍生物的重要中间体。本文通过两次取代反应得到标题化合物。该结构由 FTIR、1 H 和13证实C NMR光谱和MS。同时，通过X射线衍射检测单晶，应用密度泛函理论（DFT）计算，并进行晶体学和构象分析。DFT计算值与X射线衍射值的比较结果表明，优化后的分子结构确实与实验确定的单晶结构相一致。在 DFT 计算中发现了 98.28% 的稳定构象异构体和 1.72% 的不稳定构象异构体。此外，为了揭示标题化合物的物理化学特征，通过 DFT 研究了分子静电势和前沿分子轨道。

  DOI：

  10.1134/s0022476621090043

文献信息

• Rational design, synthesis and testing of novel tricyclic topoisomerase inhibitors for the treatment of bacterial infections part 1
  作者：R. Kirk、A. Ratcliffe、G. Noonan、M. Uosis-Martin、D. Lyth、O. Bardell-Cox、J. Massam、P. Schofield、S. Hindley、D. R. Jones、J. Maclean、A. Smith、V. Savage、S. Mohmed、C. Charrier、A-M. Salisbury、E. Moyo、R. Metzger、N. Chalam-Judge、J. Cheung、N. R. Stokes、S. Best、M. Craighead、R. Armer、A. Huxley

  DOI：10.1039/d0md00174k

  日期：——

  and topoisomerase IV inhibitors that demonstrate potent activity against a range of Gram-positive and selected Gram-negative organisms, including clinically-relevant and drug-resistant strains. In part 1, we present a detailed structure activity relationship (SAR) analysis that led to the discovery of our previously disclosed compound, REDX05931, which has a minimum inhibitory concentration (MIC) of

  针对细菌感染的药物有效性令人震惊的下降，迫切需要开发新的抗菌剂来绕过细菌耐药机制。我们在此报告了一系列 DNA 促旋酶和拓扑异构酶 IV 抑制剂，它们对一系列革兰氏阳性和选定的革兰氏阴性生物体（包括临床相关和耐药菌株）表现出有效的活性。在第 1 部分中，我们提出了详细的构效关系 (SAR) 分析，导致我们发现了我们之前公开的化合物 REDX05931，该化合物对耐氟喹诺酮类金黄色葡萄球菌的最小抑制浓度 (MIC) 为 0.06 μg mL -1。虽然在体外 hERG 和 CYP 抑制阻止了进一步的发展，它验证了一种合理的设计方法来解决这一紧迫的未满足的医疗需求，并为进一步优化提供了一个支架，在第 2 部分中介绍。
• [EN] AZABENZIMIDAZOLES AS FATTY ACID SYNTHASE INHIBITORS<br/>[FR] AZABENZAMIDAZOLES COMME INHIBITEURS D'ACIDE GRAS SYNTHASE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011066211A1

  公开（公告）日：2011-06-03

  This invention relates to the use of azabenzimidazole derivatives for the modulation, notably the inhibition of the activity or function of fatty acid synthase (FAS). Suitably, the present invention relates to the use of azabenzimidazoles in the treatment of cancer.

  这项发明涉及使用吡唑苯并咪唑衍生物来调节，特别是抑制脂肪酸合成酶（FAS）的活性或功能。适当地，本发明涉及在癌症治疗中使用吡唑苯并咪唑。
• 6-AMINOIMIDAZO[1,2-b]PYRIDAZINE ANALOGS AS RHO KINASE INHIBITORS FOR THE TREATMENT OF RHO KINASE-MEDIATED DISEASES AND CONDITIONS
  申请人：CHEN Hwang-Hsing

  公开号：US20080153813A1

  公开（公告）日：2008-06-26

  Methods for using 6-aminoimidazo[1,2-b]pyridazine analogs are disclosed herein to treat rho kinase-mediated diseases or rho kinase-mediated conditions, including controlling intraocular pressure and treating glaucoma, are disclosed. Ophthalmic pharmaceutical compositions useful in the treatment of eye diseases such as glaucoma, and additionally useful for controlling intraocular pressure, the compositions comprising an effective amount of 6-aminoimidazo[1,2-b]pyridazine analogs, are disclosed herein.

  本文披露了使用6-氨基咪唑并[1,2-b]吡啶嗪类似物治疗rho激酶介导的疾病或rho激酶介导的症状的方法，包括控制眼压和治疗青光眼。本文还披露了用于治疗眼部疾病如青光眼，并且对控制眼压有益的眼科药物组合物，该组合物包括有效量的6-氨基咪唑并[1,2-b]吡啶嗪类似物。
• Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
  申请人：Molino F. Bruce

  公开号：US20060052378A1

  公开（公告）日：2006-03-09

  The compounds of the present invention are represented by the chemical structure found in Formula (I): wherein: the carbon atom designated * is in the R or S configuration; and X is a fused bicyclic carbocycle or heterocycle selected from the group consisting of benzofuranyl, benzo[b]thiophenyl, benzoisothiazolyl, benzoisoxazolyl, indazolyl, indolyl, isoindolyl, indolizinyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, imidazo[1,2-a]pyridinyl, pyrazolo[1,5-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, thieno[2,3-b]pyridinyl, thieno[3,2-b]pyridinyl, 1H-pyrrolo[2,3-b]pyridinyl, indenyl, indanyl, dihydrobenzocycloheptenyl, tetrahydrobenzocycloheptenyl, dihydrobenzothiophenyl, dihydrobenzofuranyl, indolinyl, naphthyl, tetrahydronaphthyl, quinolinyl, isoquinolinyl, 4H-quinolizinyl, 9aH-quinolizinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, benzo[1,2,3]triazinyl, benzo[1,2,4]triazinyl, 2H-chromenyl, 4H-chromenyl, and a fused bicyclic carbocycle or fused bicyclic heterocycle optionally substituted with substituents (1 to 4 in number) as defined in R 14 ; with R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 14 defined herein.

  本发明的化合物由以下式中的化学结构表示（I）： 其中： 指定为*的碳原子处于R或S构型；X是从苯并呋喃基、苯并噻吩基、苯并异噻唑基、苯并异噁唑基、吲哚基、吲哚基、异吲哚基、吲哚啉基、苯并咪唑基、苯并噁唑基、苯并噻唑基、苯并三唑基、咪唑并[1,2-a]吡啶基、吡唑并[1,5-a]吡啶基、[1,2,4]三唑并[4,3-a]吡啶基、噻吩并[2,3-b]吡啶基、噻吩并[3,2-b]吡啶基、1H-吡咯并[2,3-b]吡啶基、茚基、茚基、二氢苯并环庚烯基、四氢苯并环庚烯基、二氢苯并噻吩基、二氢苯并呋喃基、吲啉基、萘基、四氢萘基、喹啉基、异喹啉基、4H-喹啉基、9aH-喹啉基、喹唑啉基、喜啉基、邻苯二嗪基、喹啉基、苯并[1,2,3]三嗪基、苯并[1,2,4]三嗪基、2H-香豆素基、4H-香豆素基或者是一个可选地用取代基（1至4个）取代的螺联苯环或螺联杂环的螺联双环碳环或螺联双环杂环； 其中R1、R2、R3、R4、R5、R6、R7、R8和R14在此处定义。
• The application of nitrogen heterocycles in mitochondrial-targeting fluorescent markers with neutral skeletons
  作者：Yue Wang、Bing Xu、Ru Sun、Yu-Jie Xu、Jian-Feng Ge

  DOI：10.1039/d0tb01377c

  日期：——

  1H-indazole and 1H-pyrrolo[2,3-b]pyridine) as targeting groups were designed and prepared in order to screen out structural units for targeting mitochondria. Several classical fluorophores (coumarin, 1,8-naphthalimide and Nile Red) were connected with these heterocycles via Suzuki coupling reactions. The derivatives of coumarin (dyes 1a and 2a–c) and 1,8-naphthalimide (dyes 3a–c) fluoresced in the blue-green

  设计并制备了四种不同的含氮杂环的中性荧光标记物（喹喔啉，1 H-吡唑并[3,4- b ]吡啶，1 H-吲唑和1 H-吡咯并[2,3- b ]吡啶）作为靶向基团。为了筛选出针对线粒体的结构单元。几种经典的荧光团（香豆素，1,8-萘二甲酰亚胺和尼罗红）通过Suzuki偶联反应与这些杂环连接。香豆素（染料1a和2a–c）和1,8-萘二甲酰亚胺（染料3a–c）的衍生物在蓝绿色区域发出荧光，而尼罗红衍生物（染料1b和2d）则发荧光。4a–c）在红光区域发出荧光。新染料保留了经典荧光团的光学性质，例如发射性质和光稳定性。它们均显示出低细胞毒性。在L929正常细胞和HeLa癌细胞中进行的共聚焦荧光实验表明，染料1a–b靶向线粒体和脂质液滴的双重位点。此外，染料2a–c，3a–c和4a–c靶向线粒体。同时，仅有少数具有中性骨架的线粒体靶向标记。此外，还发现带有NH键的氮杂环可以提高部分中性荧光团的线粒体靶向能力。