6-氟(1H)吲唑 | 348-25-4

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 6-氟(1H)吲唑
• 中文别名: 6-氟-1H-吲唑；6-氟吲唑
• 英文名称: 6-fluoro-1H-indazole
• CAS: 348-25-4
• 化学式: C₇H₅FN₂
• mdl: MFCD07371562
• 分子量: 136.129
• InChiKey: CFMZDEQEVCDMRN-UHFFFAOYSA-N

物化性质

• 熔点：
  126 °C (decomp)
• 沸点：
  274.9±13.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Fluoro-1H-indazole
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-Fluoro-1H-indazole
CAS number: 348-25-4

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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: C7H5FN2
Molecular weight: 136.1

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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 fluoride.

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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-氟(1H)吲唑 在 盐酸 、 manganese(IV) oxide 、 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  发现治疗急性髓系白血病的强效选择性 PI3Kδ 抑制剂

  摘要：

  PI3Kδ是与急性髓系白血病（AML）发生、发展相关的重要靶点。在此，我们研究了吡唑并[3,4- d ]嘧啶衍生物作为有效且选择性的PI3Kδ抑制剂，对AML具有较高的治疗效果。经过四轮优化设计制备了44个化合物，生物学评价表明( S )-36对MV-4-11和MOLM-13细胞表现出强效的PI3Kδ抑制活性、高选择性和高抗增殖活性。加上高口服生物利用度（ F = 59.6%）。在MOLM-13皮下异种移植模型中， ( S )-36口服剂量10 mg/kg即可显着抑制肿瘤进展，TGI为67.81%，且无明显毒性。从机制上讲， ( S )-36可以强力抑制 PI3K/AKT 通路，从而在体外和体内显着抑制细胞增殖并显着诱导细胞凋亡。因此，化合物( S )-36代表了一种有前途的PI3Kδ抑制剂，用于高效治疗急性髓系白血病。

  DOI：

  10.1021/acs.jmedchem.4c00094
• 作为产物：
  描述：

  2,4-二氟苯甲醛 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 6-氟(1H)吲唑
  参考文献：
  名称：

  新型 6-吲吲唑基-2-吡啶甲酸的设计、合成及除草活性研究

  摘要：

  通过支架跳跃设计并合成了 38 种新的 4-氨基-3,5-二吾-6-（1H-吲哚唑基）-2-吡啶酰酸和 4-氨基-3,5-二吾酰-6-（2H-吲哚唑基）-2-吆啶酰酸，以发现潜在的除草分子。对所有新化合物进行测试，以确定它们对拟南芥和五种杂草根系生长的抑制活性。总体而言，合成的化合物表现出优异的抑制性能，对杂草根系生长表现出良好的抑制作用。特别是，化合物 5a 在 10 μM 浓度的甘蓝型油菜和 Abutilon theophrasti Medicus 中显示出显著高于 picloram 的根抑制活性。大多数化合物在 250 g/hm2 时对反枝苋和藜苣表现出 100% 的苗后除草效果。我们还发现，6-吲哚唑基-2-吡啶甲酸可诱导生长素基因 ACS7 和 NCED3 的上调，而生长素内流、外排和生长素响应因子下调，表明 6-吲哚唑基-2-吡啶甲酸促进乙烯释放和 ABA 产生，在短时间内导致植株死亡，这与其他吡啶甲酸的模式不同。

  DOI：

  10.3390/molecules29020332

文献信息

• [EN] NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF<br/>[FR] STÉROÏDES NEUROACTIFS, COMPOSITIONS ET UTILISATIONS
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2015027227A1

  公开（公告）日：2015-02-26

  Described herein are neuroactive steroids of the Formula (I): or a pharmaceutically acceptable salt thereof; wherein -------, R1, R2, R5, A and L are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.

  本文描述了化学式（I）中的神经活性类固醇或其药用可接受盐；其中-------，R1，R2，R5，A和L如本文所定义。在某些实施例中，预期这些化合物将表现为GABA调节剂。本发明还提供了包括本发明化合物的药物组合物以及使用和治疗方法，例如用于诱导镇静和/或麻醉的方法。
• New CRTh2 antagonists.
  申请人：Almirall, S.A.

  公开号：EP2548863A1

  公开（公告）日：2013-01-23

  The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

  这项发明涉及到式(I)化合物，制备这种化合物的方法以及它们在治疗病理状况或疾病中的应用，这些病理状况或疾病对CRTh2拮抗活性有改善作用。
• Synthesis and structure–activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists
  作者：Itsuro Shimada、Kyoichi Maeno、Ken-ichi Kazuta、Hideki Kubota、Tetsuya Kimizuka、Yasuharu Kimura、Ken-ichi Hatanaka、Yuki Naitou、Fumikazu Wanibuchi、Shuichi Sakamoto

  DOI：10.1016/j.bmc.2007.10.100

  日期：2008.2.15

  A series of novel indazole derivatives were synthesized, and their structure-activity relationships examined in order to identify potent and selective 5-HT2C receptor agonists. Among these compounds, (S)-2-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)-1-methylethylamine (YM348) had a good in vitro profile, that is, high agonistic activity to the human 5-HT2C receptor subtype (EC50 = 1.0 nM) and high selectivity

  合成了一系列新颖的吲唑衍生物，并检查了它们的结构-活性关系，以鉴定有效的和选择性的5-HT 2C受体激动剂。在这些化合物中，（S）-2-（7-乙基-1H-呋喃[2,3-g]吲唑-1-基）-1-甲基乙胺（YM348）具有良好的体外特性，即高激动性对人5-HT2C受体亚型的活性（EC50 = 1.0 nM）和对5-HT2A受体的高选择性。口服给予该化合物在大鼠阴茎勃起模型中也有效
• 作为JAK抑制剂的化合物及其用途
  申请人：广东东阳光药业有限公司

  公开号：CN106336413B

  公开（公告）日：2021-04-20

  本发明提供作为JAK抑制剂的化合物及其用途；具体地，本发明提供一类具有JAK抑制活性的化合物(如式(I)所示)或其立体异构体，几何异构体，互变异构体，消旋体，氮氧化物，水合物，溶剂化物，代谢产物，药学上可接受的盐或前药，以及包含本发明化合物的药物组合物。本发明还公开了本发明化合物或其药物组合物在制备药物中的用途，该药物用于治疗自体免疫疾病或增殖性疾病。
• Rhodium-Catalyzed Regioselective C7-Olefination of Indazoles Using an N-Amide Directing Group
  作者：Lei Guo、Yanyu Chen、Rong Zhang、Qiujun Peng、Lanting Xu、Xianhua Pan

  DOI：10.1002/asia.201601456

  日期：2017.2.1

  A rhodium‐catalyzed regioselective C−H olefination of indazole is described. This protocol relies on the use of an efficient and removable N,N‐diisopropylcarbamoyl directing group, which offers facile access to C7‐olefinated indazoles with high regioselectivity, ample substrate scope and broad functional group tolerance.

  描述了吲哚的铑催化的区域选择性CH烯化反应。该方案依赖于使用高效，可去除的N，N-二异丙基氨基甲酰基导向基团，该基团可轻松获得具有高区域选择性，充足的底物范围和宽泛的官能团耐受性的C7烯烃基吲唑。