N,N-二甲基-3-硝基苯甲酰胺 | 7291-02-3

• 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: N,N-二甲基-3-硝基苯甲酰胺
• 英文名称: N,N-dimethyl-3-nitrobenzamide
• 英文别名: 3-nitro-N,N-dimethylbenzamide
• CAS: 7291-02-3
• 化学式: C₉H₁₀N₂O₃
• mdl: MFCD00466214
• 分子量: 194.19
• InChiKey: DKWDGIRXGDSOST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: N,N-Dimethyl-3-nitrobenzamide
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: N,N-Dimethyl-3-nitrobenzamide
CAS number: 7291-02-3

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C9H10N2O3
Molecular weight: 194.2

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N,N-二甲基-3-硝基苯甲酰胺 在 苯甲酸乙酯 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以91%的产率得到间硝基苯甲醛
  参考文献：
  名称：

  DIBALH：从已知的基本反应到不寻常的反应；在酯存在下化学选择性部分还原叔酰胺。

  摘要：

  本研究提出了一种快速可靠的方法，可在使用商业 DIBALH 试剂的易还原酯基团存在的情况下，将叔酰胺化学选择性部分还原为醛。此外，所开发的方法还扩展到带有酯部分的多功能分子，这些分子成功地化学选择性地还原为相应的醛。

  DOI：

  10.1039/d1ra06279d
• 作为产物：
  描述：

  m-nitrobenzhydroxamoyl chloride 在 乙醇 、 silver(l) oxide 、 苯 作用下， 生成 N,N-二甲基-3-硝基苯甲酰胺
  参考文献：
  名称：

  Brady; Peakin, Journal of the Chemical Society, 1929, p. 2269

  摘要：

  DOI：
• 作为试剂：
  描述：

  1,3,5-三氯苯 在 2-((双(二甲基氨基)亚甲基)氨基)-1,3-二甲基-4,5-二氢-1H-咪唑-3-鎓氯化物 potassium fluoride 、 N,N-二甲基-3-硝基苯甲酰胺 作用下， 以 环丁砜 为溶剂， 220.0 ℃ 、800.01 kPa 条件下， 反应 48.0h， 以74%的产率得到1,3,5-三氟苯
  参考文献：
  名称：

  Process for preparing ring-fluorinated aromatics

  摘要：

  本发明涉及一种改进的工艺，用于在催化剂存在的情况下通过卤素交换反应（哈莱克斯反应）在一个阶段中处理多个卤素取代基，以制备一般式（I）的环氟芳香化合物。

  公开号：

  US20060009643A1

文献信息

• 2-Arylamino-6-ethynylpurines are cysteine-targeting irreversible inhibitors of Nek2 kinase
  作者：Christopher J. Matheson、Christopher R. Coxon、Richard Bayliss、Kathy Boxall、Benoit Carbain、Andrew M. Fry、Ian R. Hardcastle、Suzannah J. Harnor、Corine Mas-Droux、David R. Newell、Mark W. Richards、Mangaleswaran Sivaprakasam、David Turner、Roger J. Griffin、Bernard T. Golding、Céline Cano

  DOI：10.1039/d0md00074d

  日期：——

  Renewed interest in covalent inhibitors of enzymes implicated in disease states has afforded several agents targeted at protein kinases of relevance to cancers. We now report the design, synthesis and biological evaluation of 6-ethynylpurines that act as covalent inhibitors of Nek2 by capturing a cysteine residue (Cys22) close to the catalytic domain of this protein kinase. Examination of the crystal

  人们对与疾病状态有关的酶的共价抑制剂重新产生了兴趣，从而提供了几种针对与癌症相关的蛋白激酶的药物。我们现在报告了 6-乙炔基嘌呤的设计、合成和生物学评价，6-乙炔基嘌呤通过捕获靠近该蛋白激酶催化结构域的半胱氨酸残基 (Cys22) 来充当 Nek2 的共价抑制剂。对与 Nek2 复合的非共价抑制剂 3-((6-环己基甲氧基-7 H-嘌呤-2-基)氨基)苯甲酰胺的晶体结构的检查表明，用乙炔基取代烷氧基放置了炔烃的末端接近Cys22并且处于与迈克尔加成的立体电子学要求兼容的位置。制备了一系列 6-乙炔基嘌呤并建立了抑制 Nek2 的结构活性关系 (SAR)。 6-乙炔基-N-苯基-7 H-嘌呤-2-胺 [IC 50 0.15 μM (Nek2)] 和 4-((6-乙炔基-7 H-嘌呤-2-基)氨基)苯磺酰胺 (IC 50 0.14)选择 Nek2 的抑制模式来确定 Nek2 的抑制模式，该抑制模式具有时间依赖性，不能通过添加
• NOVEL LOW-MOLECULAR-COMPOUND FOR IMPROVING PRODUCTION, MAINTENANCE AND PROLIFERATION OF PLURIPOTENT STEM CELLS, COMPOSITION COMPRISING THE SAME, AND CULTURE METHOD
  申请人：KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY

  公开号：US20150159142A1

  公开（公告）日：2015-06-11

  According to the present invention, when the novel low-molecular-weight compound RSC-133 is added in a culture process for producing reprogrammed pluripotent stem cells from human differentiated cells, it can increase the efficiency of reprogramming and can significantly reduce the time required for the induction of reprogramming. Particularly, the novel compound RSC-133 can substitute for c-Myc acting as both a reprogramming factor and an oncogenic factor, and it can effectively increase the efficiency of reprogramming in both normal oxygen culture conditions and hypoxic culture conditions. In addition, RSC-133 can inhibit the induction of aging occurring in the reprogramming process, exhibits the effect of promoting cell proliferation, and induces epigenetic activation to improve culture conditions for induction of reprogramming. The present invention will contribute to optimizing a process of producing induced pluripotent stem cells from a small amount of patient-specific somatic cells obtained from various sources, and thus it will significantly improve a process of developing clinically applicable personalized stem cell therapy agents and new drugs and will facilitate the practical use of these agents and drugs. In addition, the novel low-molecular-weight compound RSC-133 can provide a cell culture medium effective for maintaining the undifferentiated state of human embryonic stem cells that are typical pluripotent stem cells. The medium composition containing RSC-133 can effectively induce the proliferation of human embryonic stem cells in an undifferentiated state and can be effectively used for the development of a system for culturing large amounts of embryonic stem cells.

  根据本发明，当在从人类分化细胞生产重编程的多能干细胞的文化过程中添加新型的低分子量化合物RSC-133时，它可以提高重编程的效率，并且可以显著减少诱导重编程所需的时间。特别是，新型化合物RSC-133可以替代作为重编程因子和致癌因子的c-Myc，并且可以在正常氧文化条件和无氧文化条件下有效地提高重编程的效率。此外，RSC-133可以抑制在重编程过程中发生的衰老诱导，表现出促进细胞增殖的效果，并诱导表观遗传激活以改善重编程诱导的培养条件。本发明将有助于优化从各种来源获得的患者特异性体细胞的小量生产诱导多能干细胞的过程，从而将显著改进开发临床应用的个人化干细胞治疗剂和新药的过程，并将促进这些剂和药物的实用化。另外，新型的低分子量化合物RSC-133可以提供一个有效的细胞培养介质，用于维持典型多能干细胞的人胚胎干细胞的不分化状态。含有RSC-133的培养基质可以有效诱导人胚胎干细胞在不分化状态的增殖，并且可以有效地用于大量胚胎干细胞培养系统的开发。
• Palladium‐Catalyzed Aminocarbonylation of Aryl Halides with <i>N</i> , <i>N</i> ‐Dialkylformamide Acetals
  作者：Shuichi Hirata、Takao Osako、Yasuhiro Uozumi

  DOI：10.1002/hlca.202100162

  日期：2021.11

  We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding

  我们开发了一种在中性条件下使用毒性较低的甲酰胺缩醛作为实验室稳定的氨基羰基来源的芳基卤化物的钯催化氨基羰基化的协议。在催化量的三（二亚苄基丙酮）二钯（0）-氯仿存在下，各种芳基（包括杂芳基）卤化物与N , N - 二烷基甲酰胺缩醛反应加合物和黄磷在 90–140 °C 下生成相应的芳族甲酰胺，无需任何活化剂或碱，化学产率高达定量。该方案适用于芳基溴化物、芳基碘化物和三氟甲磺酸，以及反应性相对较低的芳基氯化物。在氨基羰基化条件下，可以容忍底物芳环上的各种官能团。催化氨基羰基化反应制备了驱虫剂N , N-二乙基-3-甲基苯甲酰胺以及二氢叶酸还原酶抑制剂三嗪酸盐的合成中间体。
• Development of Potent Pyrazolopyrimidinone-Based WEE1 Inhibitors with Limited Single-Agent Cytotoxicity for Cancer Therapy
  作者：Christopher J. Matheson、Kimberly A. Casalvieri、Donald S. Backos、Philip Reigan

  DOI：10.1002/cmdc.201800188

  日期：2018.8.20

  DNA‐damaging agents. We previously reported a series of pyrazolopyrimidinones based on AZD1775, a known WEE1 inhibitor, as an initial investigation into the structural requirements for WEE1 inhibition. Our lead inhibitor demonstrated WEE1 inhibition in the same nanomolar range as AZD1775, and potentiated the effects of cisplatin in medulloblastoma cells, but had reduced single‐agent cytotoxicity. These results

  WEE1激酶调节G 2/ M细胞周期检查点，这是癌细胞中DNA修复的重要机制，可以赋予对DNA破坏剂的抗性。我们先前报道了一系列基于AZD1775（已知的WEE1抑制剂）的吡唑并吡喃二酮，作为对WEE1抑制作用的结构要求的初步研究。我们的先导抑制剂在与AZD1775相同的纳摩尔范围内表现出对WEE1的抑制作用，并增强了顺铂在髓母细胞瘤细胞中的作用，但降低了单药的细胞毒性。这些结果促使开发了更全面的WEE1抑制剂系列。在本文中，我们报告了一系列吡唑并嘧啶酮，并确定了比AZD1775更有效的WEE1抑制剂和其他化合物，这些化合物证明可以通过降低单药细胞毒性来实现WEE1抑制。
• Unusual behaviour of N-bromosuccinimide. Conversion of N,N-dimethylamides to N-methyl,N-succinimidomethylamides
  作者：C. Caristi、G. Cimino、A. Ferlazzo、M. Gattuso、M. Parisi

  DOI：10.1016/s0040-4039(00)87977-0

  日期：1983.1

  N,N-Dimethylamides are converted by NBS to the N-succinimidomethylamides in an almost quantitative yield. The intermediacy of bromomethylderivatives which further react with NBS to give is demonstrated.

  N，N-二甲基酰胺被NBS以几乎定量的产率转化为N-琥珀酰亚胺基甲基酰胺。证明了溴甲基衍生物进一步与NBS反应生成中间体。