5-溴-2-甲氧基苯甲酰胺 | 303111-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-溴-2-甲氧基苯甲酰胺
• 英文名称: 5-bromo-2-methoxybenzamide
• CAS: 303111-31-1
• 化学式: C₈H₈BrNO₂
• mdl: MFCD08105424
• 分子量: 230.061
• InChiKey: VWRKGVNZHGRWSV-UHFFFAOYSA-N

物化性质

• 熔点：
  153-154 °C(Solv: ethanol (64-17-5))
• 沸点：
  304.0±32.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-2-methoxybenzamide
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-Bromo-2-methoxybenzamide
CAS number: 303111-31-1

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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: C8H8BrNO2
Molecular weight: 230.1

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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-2-甲氧基苯甲酰胺 在 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 ((S)-1-Benzyl-pyrrolidin-3-ylmethyl)-[2-(5-bromo-2-methoxy-phenyl)-oxazol-4-ylmethyl]-amine
  参考文献：
  名称：

  苯恶唑和苯基噻唑作为苯甲酰胺的生物等排体：合成和多巴胺受体结合特征。

  摘要：

  当氨基甲基吡咯烷衍生物4o证明了D3和D4的结合特性分别与非典型的抗精神病药舒必利和氯氮平相当时，研究了构象受限的苯甲酰胺生物异构体。

  DOI：

  10.1016/s0960-894x(00)00405-4
• 作为产物：
  描述：

  2-乙基苯甲醚 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 、 碘 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 30.0h， 生成 5-溴-2-甲氧基苯甲酰胺
  参考文献：
  名称：

  N-溴代琥珀酰亚胺和I 2 -NH 3水溶液将乙炔直接转化为伯芳酰胺

  摘要：

  通过在乙酸乙酯和水，乙腈和水的混合物中催化量的2,2'-偶氮二（异丁腈）存在下用N-溴琥珀酰亚胺处理，将各种乙基芳烃高收率转化为相应的伯芳族酰胺。，或氯仿和水，然后在一个锅中与分子碘和NH 3水溶液反应。发现在第一反应步骤中形成芳基α-溴甲基酮和/或芳基甲基酮，并且在第二反应步骤中发生它们的碘仿型反应以提供伯芳族酰胺。本反应是用于从乙基芳烃制备伯芳族酰胺的有用且实用的无过渡金属的方法。

  DOI：

  10.1021/acs.orglett.6b00048

文献信息

• Condensed derivatives of imidazole useful as pharmaceuticals
  申请人：LABORATOIRE BIODIM

  公开号：EP2913330A1

  公开（公告）日：2015-09-02

  The invention relates to the compounds (I) and their acids and bases salts: wherein: the dotted line indicates a double bond; X is N or C-R1 and Y is N or C-R2, X and Y not being simultaneously N; A is selected from the group consisting of phenyl, naphthyl and (5-11) membered monocyclic or bicyclic unsaturated cycle or heterocycle possibly substituted as defined in the application, and A can also comprise either a further (4-7) membered heterocycle, said heterocycle being a monocycle, fused, saturated or unsaturated, the polycyclic system then comprising up to 14 members and up to 5 heteroatoms selected from N, O and S; B is Hydrogen or a substituent as defined in the application, or B is a (4-10) membered mono or bicyclic saturated or unsaturated heterocycle containing 1-3 heteroatoms selected from N, O and S, and possibly substituted as defined in the application; B not being Hydrogen when X is N and Y is C-R2; R1 is Hydrogen or a substituent as defined in the application; B and R1 cannot be simultaneously Hydrogen; R2 is Hydrogen or Halogen; their preparation, their use in the antibacterial prevention and therapy, alone or in association with antibacterials, antivirulence agents or drugs reinforcing the host innate immunity, and pharmaceutical compositions and associations containing them.

  该发明涉及化合物（I）及其酸盐和碱盐： 其中： 虚线表示双键； X为N或C-R1，Y为N或C-R2，X和Y不同时为N； A选自苯基、萘基和（5-11）成员单环或双环不饱和环或杂环，可能按申请中定义进行取代， A还可以包括另一个（4-7）成员杂环，该杂环为单环、融合、饱和或不饱和，多环系统则包括最多14个成员和最多5个N、O和S中选择的杂原子； B为氢或按申请中定义的取代基，或 B为含有1-3个N、O和S中选择的杂原子的（4-10）成员单环或双环饱和或不饱和杂环，并可能按申请中定义进行取代； 当X为N且Y为C-R2时，B不是氢； R1为氢或按申请中定义的取代基； B和R1不能同时为氢； R2为氢或卤素； 它们的制备，它们在抗菌预防和治疗中的用途，单独或与抗菌药物、抗毒力剂或增强宿主先天免疫力的药物联合使用，以及含有它们的药物组合物和联合物。
• Cyclic Amidines as Benzamide Bioisosteres: EPC Synthesis and SAR Studies Leading to the Selective Dopamine D4 Receptor Agonist FAUC 312
  作者：Jürgen Einsiedel、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(03)00004-0

  日期：2003.3

  Investigation of conformationally restricted benzamide bioisosteres led to the chiral phenyltetrahydropyrimidine derivative ent2a (FAUC 312) displaying strong and highly selective dopamine D4 receptor binding (K(i(high))=1.5 nM). Mitogenesis experiments indicated 83% ligand efficacy when compared to the unselective agonist quinpirole. The target compounds of type 2 and 3 were synthesized in enantiopure

  构象受限的苯甲酰胺生物等位基因的研究导致手性苯基四氢嘧啶衍生物ent2a（FAUC 312）表现出强而高度选择性的多巴胺D4受体结合（K（i（high））= 1.5 nM）。与非选择性激动剂喹吡罗相比，有丝分裂实验表明配体效力为83％。从天冬酰胺开始以对映纯形式合成2型和3型目标化合物。
• Discovery of GS-9973, a Selective and Orally Efficacious Inhibitor of Spleen Tyrosine Kinase
  作者：Kevin S. Currie、Jeffrey E. Kropf、Tony Lee、Peter Blomgren、Jianjun Xu、Zhongdong Zhao、Steve Gallion、J. Andrew Whitney、Deborah Maclin、Eric B. Lansdon、Patricia Maciejewski、Ann Marie Rossi、Hong Rong、Jennifer Macaluso、James Barbosa、Julie A. Di Paolo、Scott A. Mitchell

  DOI：10.1021/jm500228a

  日期：2014.5.8

  expected that a more selective Syk inhibitor would provide a greater therapeutic window. Herein we report the discovery and optimization of a novel series of imidazo[1,2-a]pyrazine Syk inhibitors. This work culminated in the identification of GS-9973, 68, a highly selective and orally efficacious Syk inhibitor which is currently undergoing clinical evaluation for autoimmune and oncology indications.

  脾酪氨酸激酶（Syk）在自身免疫，炎症和肿瘤疾病适应症中是有吸引力的药物靶标。最先进的Syk抑制剂，R406，1（或它的前药形式fostamatinib，2），已在多个治疗适应症中显示出功效，但其临床进展已经由已被归因，至少部分剂量限制性不利影响的阻碍，到的脱靶活性1。预期选择性更高的Syk抑制剂将提供更大的治疗窗口。在本文中，我们报告了一系列新型咪唑并[1,2- a ]吡嗪Syk抑制剂的发现和优化。这项工作在GS-9973，鉴定高潮68是一种高度选择性和口服有效的Syk抑制剂，目前正在针对自身免疫和肿瘤学适应症进行临床评估。
• Discovery of 6-benzamide Containing 4-phenylquinazoline Derivatives as Novel PI3Kδ Inhibitors
  作者：Minhang Xin、Yuan-Yuan Hei、Hao Zhang、Xiao-Xiao Xie、Shuai Mao、Sai-Jie Zuo、San-Qi Zhang

  DOI：10.2174/1570180813666160720160523

  日期：2016.12.21

  In the present study, a series of new 6-benzamide containing 4-phenylquinazoline derivatives were designed and synthesized as PI3Kδ inhibitors. The preliminary SAR for this series of compounds was established. PI3Kδ inhibitory assay showed that most of the synthesized compounds achieved significant activity against PI3Kδ. Compound 12h was the most potent PI3Kδ inhibitor, displaying an IC50 value of

  在本研究中，设计并合成了一系列新型的含有4-苯基喹唑啉的6-苯甲酰胺衍生物作为PI3Kδ抑制剂。建立了该系列化合物的初步SAR。PI3Kδ抑制试验表明，大多数合成的化合物均具有显着的抗PI3Kδ活性。化合物12h是最有效的PI3Kδ抑制剂，IC 50值为17 nM。这些结果表明，含有6-苯甲酰胺的4-苯基喹唑啉是一种令人鼓舞的化学亚结构，值得进一步的结构探索，以鉴定出新型且高效的PI3Kδ抑制剂。
• Design and synthesis of novel 6-aryl substituted 4-anilinequinazoline derivatives as potential PI3Kδ inhibitors
  作者：Minhang Xin、Yuan-Yuan Hei、Hao Zhang、Ying Shen、San-Qi Zhang

  DOI：10.1016/j.bmcl.2017.03.020

  日期：2017.5

  In this study, a series of new 6-aryl substituted 4-anilinequinazolines was designed and synthesized as PI3Kδ inhibitors based on our reported chemical structures. The preliminary structure-activity relationship (SAR) was established, and compounds 13h and 13k displayed most potent PI3Kδ inhibitory activities with the IC50 values of 9.3nM and 9.7nM, respectively. Compound 13h demonstrated similar anti-proliferative

  在这项研究中，根据我们报道的化学结构，设计并合成了一系列新型的6-芳基取代的4-苯胺喹唑啉类化合物作为PI3Kδ抑制剂。建立了初步的构效关系（SAR），化合物13h和13k显示出最有效的PI3Kδ抑制活性，IC50值分别为9.3nM和9.7nM。化合物13h对三种人类B细胞系表现出了与艾得拉西类似的抗增殖特性。在与PI3Kδ酶的13h对接中发现了三个关键的氢键相互作用。这些结果表明化合物13h具有纳摩尔PI3Kδ抑制活性和独特的化学结构，值得进一步的结构优化。