3-溴-5-硝基苯甲酰胺 | 54321-80-1

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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: 3-溴-5-硝基苯甲酰胺
• 英文名称: 3-bromo-5-nitrobenzamide
• 英文别名: 5-bromo-3-nitrobenzamide；3-Brom-5-nitrobenzamid
• CAS: 54321-80-1
• 化学式: C₇H₅BrN₂O₃
• 分子量: 245.032
• InChiKey: WNYWPPUDAKYNIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 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：
  88.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2924299090
• 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: 3-Bromo-5-nitrobenzamide
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: 3-Bromo-5-nitrobenzamide
CAS number: 54321-80-1

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H5BrN2O3
Molecular weight: 245.0

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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 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

3-溴-5-硝基苯甲酰胺是一种多聚腺苷二磷酸核糖聚合酶抑制剂，作为一种抗肿瘤试剂，目前正处于临床研究阶段。

制备

将3.7克3-溴-5-硝基苯甲酸甲酯和30毫升甲醇加入反应瓶中，在35℃下搅拌并通入氨气。通过薄层色谱（TLC）监测反应进程，采用乙酸乙酯：石油醚体积比为1:1的展开剂。反应完成后，将反应液蒸干得到约3.3克黄色固体粗品。随后，用19.8毫升乙醇对粗品进行重结晶，抽滤后，在真空条件下干燥，最终获得3.0克3-溴-5-硝基苯甲酰胺，HPLC纯度为99.75%，收率为85.2%。

反应信息

• 作为反应物：
  描述：

  3-溴-5-硝基苯甲酰胺 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 生成 3-amino-5-bromobenzamide
  参考文献：
  名称：

  Discovery of 2-methoxy-3-phenylsulfonamino-5-(quinazolin-6-yl or quinolin-6-yl)benzamides as novel PI3K inhibitors and anticancer agents by bioisostere

  摘要：

  2-Substituted-3-sulfonamino-5-(quinazolin-6-yl or quinolin-6-yl)benzamides have been proposed as novel structures of PI3K inhibitors and anticancer agents based on bioisostere. In the present study, 2-substituted-3-sulfonamino-5-(4-morpholinoquinazolin-6-yl)benzamides and 2-methoxy-3-sulfonamino-5-(4-morpholinoquinolin-6-yl)benzamides were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against four human cancer cell lines, including A549, HCT-116, U-87 MG and KB. The SAR of the title compounds was preliminarily discussed. Compound 1a with potent antiproliferative activity was tested for its inhibitory activity against MK and mTOR and its effect on the AKT and p-AKT(473). The anticancer effect of la was evaluated in established nude mice U-87 MG xenograft model. The results suggest that compound la can significantly inhibit PI3K/AKT/mTOR pathway and tumor growth. These findings strongly support the assumption that title compounds are potent PI3K inhibitors and anticancer agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.053
• 作为产物：
  描述：

  3-溴-5-硝基苯甲酸 在 ammonium hydroxide 、 氯化亚砜 作用下， 反应 2.0h， 生成 3-溴-5-硝基苯甲酰胺
  参考文献：
  名称：

  Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series

  摘要：

  We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl)ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl)ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.047

文献信息

• Combination of 2-methoxy-3-phenylsulfonylaminobenzamide and 2-aminobenzothiazole to discover novel anticancer agents
  作者：Huan Li、Xiao-Meng Wang、Juan Wang、Teng Shao、Yi-Ping Li、Qi-Bing Mei、She-Min Lu、San-Qi Zhang

  DOI：10.1016/j.bmc.2014.04.064

  日期：2014.7

  antiproliferative activity was examined for its effect on the AKT and p-AKT473. The anticancer effect of 1g was evaluated in established nude mice HCT-116 xenograft model. The results suggested that compound 1g can block PI3K/AKT/mTOR pathway and significantly inhibit tumor growth. These findings strongly support our assumption that the fragment of benzamide can replace the pyridine ring in some PI3K and mTOR dual

  已经提出了2-取代的-3-磺酰基氨基苯甲酰胺的片段来代替PI3K和mTOR双重抑制剂中的2-取代的-3-磺酰基氨基吡啶的片段，以设计基于生物等排体的新型抗癌剂。2-取代的3-磺酰基氨基苯甲酰胺的片段与2-氨基苯并噻唑或2-氨基噻唑并[5,4- b ]吡啶或2-氨基[1,2,4]三唑并[1,5-]的片段的组合一个]吡啶制备抗癌剂的新颖结构。结果，合成并表征了十九种目标化合物。通过MTT测定法评估了它们在体外对四种人类癌细胞系的体外抗增殖活性，所述细胞系包括HCT-116，A549，MCF-7和U-87 MG。初步讨论了目标化合物的SAR。化合物1g研究了具有强抗增殖活性的化合物对AKT和p-AKT 473的作用。在已建立的裸鼠HCT-116异种移植模型中评估了1g的抗癌作用。结果表明，化合物1g可以阻断PI3K / AKT / mTOR通路，并显着抑制肿瘤的生长。这些发现强烈支持我们的假设，
• Bromination of Deactivated Aromatics: A Simple and Efficient Method
  作者：K. Rajesh、M. Somasundaram、R. Saiganesh、K. K. Balasubramanian

  DOI：10.1021/jo070477u

  日期：2007.7.1

  Highly deactivated aromatic compounds were smoothly monobrominated by treatment with N-bromosuccinimide (NBS) in concentrated H2SO4 medium affording the corresponding bromo derivatives in good yields. Mild reaction conditions and simple workup provides a practical and commercially viable route for the synthesis of bromo compounds of deactivated aromatics.

  通过在浓H 2 SO 4介质中用N-溴琥珀酰亚胺（NBS）处理，将高度失活的芳族化合物顺利地单溴化，从而以高收率得到相应的溴衍生物。温和的反应条件和简单的后处理为合成失活的芳族化合物的溴化物化合物提供了实用且商业上可行的途径。
• 一种自催化氰源一锅法制备芳基伯酰胺的方法
  申请人：杭州微流汇科技有限公司

  公开号：CN114685308A

  公开（公告）日：2022-07-01

  本发明公开一种自催化氰源一锅法制备芳基伯酰胺的方法，实施过程以如式(1)所示的化合物作为起始原料，无需贵金属催化剂，无需配体，以有机溶剂和水为反应溶剂，在碱性条件下，由氰源引入氰基，最终生成如式(2)所示的芳基伯酰胺化合物，反应方程式为:取代基为R(n)，n＝1‑3，n取整数，R(n)选自氢、甲基、乙基、叔丁基、硝基、甲氧基、羰基、醛基、氨基甲酰基、N‑甲基氨基甲酰基、N‑甲基‑N‑烯丙基氨基甲酰基、酯基或卤素；Ar为苯基、噻吩基、萘基、吡啶基、喹啉基、吲哚基、呋喃基、吡咯基、咪唑基或噻唑基。本发明由芳基溴代物制备芳基酰胺，具有无需贵金属催化剂、无需配体、底物适应广、操作简单、转化率和选择性高等优点。
• Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series
  作者：David Alagille、Herve DaCosta、Yelin Chen、Kamondanai Hemstapat、Alice Rodriguez、Ronald M. Baldwin、Jeffrey P. Conn、Gilles D. Tamagnan

  DOI：10.1016/j.bmcl.2011.04.047

  日期：2011.6

  We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl)ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl)ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity. (C) 2011 Elsevier Ltd. All rights reserved.
• PISKOV V. B.; KASPEROVICH V. P.; YAKOVLEVA L. M., XIMIYA GETEROTSIKL. SOEDIN., 1976, HO 8, 1112-1118
  作者：PISKOV V. B.、 KASPEROVICH V. P.、 YAKOVLEVA L. M.

  DOI：——

  日期：——