2-氟-5-溴吡啶-3-甲醛 | 875781-15-0

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氟-5-溴吡啶-3-甲醛
• 中文别名: 2-氟-5-溴烟醛；5-溴-2-氟-3-吡啶甲醛；5-溴-2-氟吡啶-3-甲醛
• 英文名称: 5-bromo-2-fluoronicotinaldehyde
• 英文别名: 5-bromo-2-fluoropyridine-3-carbaldehyde；5-bromo-2-fluoropyridine-3-carboxaldehyde
• CAS: 875781-15-0
• 化学式: C₆H₃BrFNO
• 分子量: 203.998
• InChiKey: MUYVOGAJRCBWCY-UHFFFAOYSA-N

物化性质

• 沸点：
  258.2±35.0 °C(Predicted)
• 密度：
  1.778±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  2-8°C，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
5-Bromo-2-fluoropyridine-3-carboxaldehyde
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
5-Bromo-2-fluoropyridine-3-carboxaldehyde
Ingredient name:
CAS number: 875781-15-0

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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, refrigerated.

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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: C6H3BrFNO
Molecular weight: 204.0

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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, nitrogen oxides, hydrogen fluoride, 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

制备方法与用途

应用

2-氟-5-溴吡啶-3-甲醛是一种吡啶类衍生物，主要用于有机合成和医药化学领域，也可作为助染剂、消毒剂以及染料的合成原料。

制备

在0℃下，通过加料漏斗向LDA溶液中缓慢加入2-氟-5-溴吡啶（11.1克，63.2毫摩尔，1.0当量）溶解于四氢呋喃（90毫升）中的溶液，并在此温度下搅拌15分钟。随后，在1.5小时后，继续以滴加方式缓慢加入甲酸乙酯（10.3毫升，127毫摩尔，2.0当量），并在滴加结束后再搅拌1小时。接着，用饱和氯化铵水溶液和乙酸（18毫升）的混合物淬灭反应，并将得到的浆液加热至25℃。加入约20克硫酸钠后过滤并进行真空浓缩，最后从二氯甲烷中重结晶提纯即可获得2-氟-5-溴吡啶-3-甲醛。

反应信息

• 作为反应物：
  描述：

  2-氟-5-溴吡啶-3-甲醛 在 hydrazine hydrate 作用下， 以 水 为溶剂， 反应 15.0h， 以82%的产率得到5-溴-1H-吡唑[3,4-B]吡啶
  参考文献：
  名称：

  醋酸锌促进的杂芳香胺的布赫瓦尔德-哈特维格偶联

  摘要：

  锌盐已显示出促进布赫瓦尔德-哈特维希与杂芳基氯化物的氮杂吲哚和氮杂吲唑的耦合，得到相应的1-芳基1 ħ -azaindoles和1-芳基1 ħ -azaindazoles。探索了该反应的底物范围和机理方面。

  DOI：

  10.1021/acs.joc.7b01101
• 作为产物：
  描述：

  2-氟-5-溴吡啶 在 正丁基锂 、 lithium diisopropyl amide 、 哌啶-1-甲醛 、 柠檬酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 1.77h， 以52%的产率得到2-氟-5-溴吡啶-3-甲醛
  参考文献：
  名称：

  [EN] FUSED RING HETEROCYCLE KINASE MODULATORS
  [FR] MODULATEURS HETEROCYCLIQUES A CYCLES FUSIONNES POUR LES KINASES

  摘要：

  公开号：

  WO2006015124A3

文献信息

• [EN] BIARYL KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES À BASE DE BIARYLE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2017059085A1

  公开（公告）日：2017-04-06

  The present disclosure is directed to biaryl compounds of formula (I) which can inhibit AAKl (adaptor associated kinase 1), compositions comprising such compounds and their use for treating e.g. pain, Alzheimer's disease, Parkinson's disease and schizophrenia.

  本公开涉及式(I)的双芳基化合物，该化合物能够抑制AAK1（适配器相关激酶1），包含此类化合物的组合物以及它们用于治疗例如疼痛、阿尔茨海默病、帕金森病和精神分裂症。
• [EN] INHIBITORS OF RAF KINASES<br/>[FR] INHIBITEURS DE KINASES RAF
  申请人：KINNATE BIOPHARMA INC

  公开号：WO2020227020A1

  公开（公告）日：2020-11-12

  Provided herein are heteroaryl inhibitors of receptor tyrosine kinase effector (RAF), pharmaceutical compositions comprising said compounds, and methods for using said compounds for the treatment of disease.

  本文件提供了受体酪氨酸激酶效应器（RAF）的杂芳基抑制剂，包括含有该化合物的药物组合物，以及使用这些化合物治疗疾病的方法。
• [EN] 3-(1H-PYRROLO[2,3-C]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINES AND THERAPEUTIC USES THEREOF<br/>[FR] 3-(1H-PYRROLO[2,3-C]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINES ET SES UTILISATIONS THÉRAPEUTIQUES
  申请人：SAMUMED LLC

  公开号：WO2017023981A1

  公开（公告）日：2017-02-09

  7-Azaindazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of a 7-azaindazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.

  7-氮杂吲唑化合物用于治疗各种疾病和病理已被披露。更具体地，本公开涉及使用7-氮杂吲唑化合物或其类似物，治疗通过激活Wnt途径信号（例如癌症、异常细胞增殖、血管生成、纤维化疾病、骨骼或软骨疾病和骨关节炎）表征的疾病，调节由Wnt途径信号介导的细胞事件，以及由于Wnt途径和/或一个或多个Wnt信号组分的突变或失调而导致的遗传疾病和神经病理状况/障碍/疾病。还提供了治疗与Wnt相关疾病状态的方法。
• Aryl nitrogen-containing bicyclic compounds and methods of use
  申请人：Patel F. Vinod

  公开号：US20070054916A1

  公开（公告）日：2007-03-08

  The present invention comprises a new class of compounds useful for the prophylaxis and treatment of protein kinase mediated diseases, including inflammation, cancer and related conditions. The compounds have a general Formula I wherein A 1 , A 2 , A 3 , B, R 1 , R 2 , R 3 and R 4 are defined herein. Accordingly, the invention also comprises pharmaceutical compositions comprising the compounds of the invention, methods for the prophylaxis and treatment of kinase mediated diseases using the compounds and compositions of the invention, and intermediates and processes useful for the preparation of compounds of the invention.

  这项发明涉及一类新的化合物，用于预防和治疗蛋白激酶介导的疾病，包括炎症、癌症和相关疾病。这些化合物具有一般的化学式I，其中A1、A2、A3、B、R1、R2、R3和R4在此有定义。因此，该发明还涉及包括该发明的化合物的药物组合物，使用该发明的化合物和组合物预防和治疗激酶介导的疾病的方法，以及用于制备该发明的化合物的中间体和方法。
• [EN] ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：ALIOS BIOPHARMA INC

  公开号：WO2015026792A1

  公开（公告）日：2015-02-26

  Disclosed herein are new antiviral compounds, together with pharmaceutical compositions that include one or more antiviral compounds, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a paramyxovirus viral infection with one or more small molecule compounds. Examples of paramyxovirus infection include an infection caused by human respiratory syncytial virus (RSV).

  本文披露了新的抗病毒化合物，以及包括一种或多种抗病毒化合物的药物组合物，以及合成这些化合物的方法。本文还披露了使用一种或多种小分子化合物改善和/或治疗副粘病毒病毒感染的方法。副粘病毒感染的例子包括由人类呼吸道合胞病毒（RSV）引起的感染。