4-溴-3-硝基苯甲酰胺 | 879-93-6

• 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: 4-溴-3-硝基苯甲酰胺
• 英文名称: 4-bromo-3-nitrobenzamide
• CAS: 879-93-6
• 化学式: C₇H₅BrN₂O₃
• mdl: MFCD00462259
• 分子量: 245.032
• InChiKey: XEXLVJPVLGTROT-UHFFFAOYSA-N

物化性质

• 沸点：
  297.7±25.0 °C(Predicted)
• 密度：
  1.799±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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

• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-3-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: 4-Bromo-3-nitrobenzamide
CAS number: 879-93-6

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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: 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

反应信息

• 作为反应物：
  描述：

  4-溴-3-硝基苯甲酰胺 在 三丁基膦 、 sodium iodide 、 nickel dibromide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 18.0h， 以54%的产率得到3-硝基-4-碘苯甲酰胺
  参考文献：
  名称：

  镍和芳基溴化物的镍催化芳族Finkelstein反应。

  摘要：

  已经开发了快速和有效的镍催化的芳基和杂芳基溴化物的碘化反应。发现该转化对于广泛的底物而言是通用的，并且用于合成阿尔茨海默氏病的显像剂碘-PK11195和用于治疗乳腺癌的化合物伊尼帕里（iniparib）。

  DOI：

  10.1039/c2cc30956d
• 作为产物：
  描述：

  4-溴-3-硝基苯甲酰氯 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-溴-3-硝基苯甲酰胺
  参考文献：
  名称：

  作为治疗阿尔茨海默病的有效 GSK-3β/DYRK1A 双重抑制剂的去氢骆驼蓬碱衍生物的设计、合成和生物学评价

  摘要：

  阿尔茨海默病（AD）是一种慢性进行性神经退行性疾病，其特征是不可逆的认知障碍、记忆丧失和行为障碍，最终导致死亡。糖原合酶激酶 3β (GSK-3β) 和双特异性酪氨酸磷酸化调节激酶 1A (DYRK1A) 因其在 tau 病理学中的作用而受到广泛关注。为了寻找潜在的 GSK-3β/DYRK1A 双重抑制剂，我们重点研究了去氢骆驼蓬碱，一种天然β-咔啉生物碱，其预防 AD 的多种生物学效应已被广泛研究。在本研究中，设计、合成了一系列新的去氢骆驼蓬碱衍生物，并评估其作为 GSK-3β/DYRK1A 双重抑制剂的多种生物活性。体外结果表明，它们中的大多数对 GSK-3β 和 DYRK1A 表现出有希望的活性。其中，化合物ZDWX-25对GSK-3β和DYRK1A表现出有效的抑制作用，IC 50值分别为71和103 nM。分子模型和动力学研究证实ZDWX-25可以与 GSK-3β 和 DYRK1A

  DOI：

  10.1016/j.ejmech.2021.113554

文献信息

• Catalytic, Diastereoselective 1,2-Difluorination of Alkenes
  作者：Steven M. Banik、Jonathan William Medley、Eric N. Jacobsen

  DOI：10.1021/jacs.6b02391

  日期：2016.4.20

  with all types of substitution patterns. In general, the vicinal difluoride products are produced with high diastereoselectivities. The observed sense of stereoinduction implicates anchimeric assistance pathways in reactions of alkenes bearing neighboring Lewis basic functionality.

  我们描述了一种直接催化烯烃 1,2-二氟化的方法。该方法利用亲核氟化物源和氧化剂以及芳基碘化物催化剂，适用于具有所有类型取代模式的烯烃。一般来说，邻位二氟化物产物具有高非对映选择性。观察到的立体诱导感暗示具有邻近路易斯基本官能团的烯烃反应中的嵌合辅助途径。
• Nickel-Mediated Radioiodination of Aryl and Heteroaryl Bromides: Rapid Synthesis of Tracers for SPECT Imaging
  作者：Alastair A. Cant、Sue Champion、Rajiv Bhalla、Sally L. Pimlott、Andrew Sutherland

  DOI：10.1002/anie.201302800

  日期：2013.7.22

  Rapid and efficient radioiodination of aryl and heteroaryl bromides has been achieved using a nickel(0)‐mediated halogen‐exchange reaction. This transformation gives direct access to [123I]‐ and [125I]‐imaging agents for single photon emission computed tomography (SPECT), such as 5‐[123I]‐A85380 (see scheme, Boc=tert‐butyloxycarbonyl, cod=1,5‐cyclooctadiene, TFA=trifluoroacetic acid).

  使用镍（0）介导的卤素交换反应已实现了芳基和杂芳基溴化物的快速有效碘化。此转换可直接访问用于单光子发射计算机断层扫描（SPECT）的[ 123 I]-和[ 125 I]-成像剂，例如5- [ 123 I] -A85380（请参阅方案，Boc =叔丁氧羰基，化学需氧量= 1,5-环辛二烯，TFA =三氟乙酸）。
• β-咔波啉类GSK3β/DYRK1A双重抑制剂及其制备方法和抗阿尔兹海默病的应用
  申请人：中国人民解放军北部战区总医院

  公开号：CN113072552B

  公开（公告）日：2022-11-04

  本发明公开了一种通式I所示的β‑咔波啉类GSK3β/DYRK1A双重抑制剂及其制备方法和抗阿尔兹海默病的应用，本发明的新型β‑咔波啉衍生物具有GSK3β/DYRK1A双重抑制活性，并提供所述β‑咔波啉类衍生物作为GSK3β/DYRK1A双重抑制剂的制备方法，同时还指出β‑咔波啉类衍生物在制备治疗阿尔兹海默病药物中的应用。该类β‑咔波啉衍生物可为发现新的AD治疗药物提供理论依据。
• Schoepff, Chemische Berichte, 1890, vol. 23, p. 3442
  作者：Schoepff

  DOI：——

  日期：——
• Nucleophilic Substitution Reactions of 1-Halogeno-4-COR-2-nitrobenzenes and 1-Halogeno-6-COR-2-nitrobenzenes with Sodium Benzenethiolate and Piperidine. Can an “Inverted Built-In Solvation” Be Responsible for the Peculiar Activation by an <i>o</i>-Carboxamido Group in S_NAr Reactions with an Anionic Nucleophile?
  作者：Caterina Arnone、Giovanni Consiglio、Vincenzo Frenna、Domenico Spinelli

  DOI：10.1021/jo961040h

  日期：1997.5.1

  A kinetic study of the title reactions has allowed an interpretation of the higher efficiency of an o-carboxamido group with respect to an o-carbomethoxy group in activating the benzenethiolate-dehalogenation reactions in methanol (k(CONH2)/k(CO2Me) 2.2-3.0) as due to an interaction between the anionic nucleophile and the hydrogen atoms of the carboxamido group. An inversion of the activating power of the two groups (kCONH(2)/k(CO2Me) 0.14) in the reactions with the same nucleophile has been observed when they are in a para-position. Moreover, for piperidino-dehalogenation reactions in methanol k(CONH2)/k(CO2Me) ratios less than unity (0.2-0.6) have been observed independently of the position (ortho or para) of the carboxamido and carbomethoxy groups with respect to the reaction center.