2-溴-N,N-二甲基苯甲酰胺 | 54616-47-6

• 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: 2-溴-N,N-二甲基苯甲酰胺
• 中文别名: 2-溴-N,N-二甲基苯酰胺；2溴N,N -二甲基苯甲酰胺
• 英文名称: 2-bromo-N,N-dimethylbenzamide
• CAS: 54616-47-6
• 化学式: C₉H₁₀BrNO
• mdl: MFCD00463635
• 分子量: 228.088
• InChiKey: JYWWETIYYPKRBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  133-136 °C(Press: 1.0 Torr)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

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
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N,N-Dimethyl 2-bromobenzamide
Synonyms: 2-Bromo-N,N-dimethylbenzamide

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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: N,N-Dimethyl 2-bromobenzamide
CAS number: 54616-47-6

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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: C9H10BrNO
Molecular weight: 228.1

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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：

  2-溴-N,N-二甲基苯甲酰胺 在 palladium diacetate 、 Wilkinson's catalyst 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 正丁基锂 、 四甲基乙二胺 、 sodium hydride 、 sodium t-butanolate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 生成 奥卡西平
  参考文献：
  名称：

  New synthesis of oxcarbazepine via remote metalation of protected N-o-tolyl-anthranilamide derivatives

  摘要：

  Benzyl and allyl protected N-o-tolyl-anthranilamides were efficiently prepared by Buchwald-Hartwig C-N cross coupling reactions, followed by protection of the amino group. Under directed remote metalation conditions, protected dibenzoazepinones were obtained in good yields. Deprotection of the amine and conversion to an urea furnished a new and efficient synthesis of the antiepileptic drug Trileptal((R)). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01981-x
• 作为产物：
  描述：

  N,N-二甲基苯甲酰胺 在 N-溴代丁二酰亚胺(NBS) 、 silver hexafluoroantimonate 、 三氟甲磺酸 、 nickel diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以77%的产率得到2-溴-N,N-二甲基苯甲酰胺
  参考文献：
  名称：

  缺电子芳烃的镍催化区域选择性C–H卤化†

  摘要：

  开发了一种简单的Ni（II）催化的一般策略，用于用易获得的卤化试剂N-卤代琥珀酰亚胺（NXS; X = Br，Cl和I）对电子缺陷型芳烃进行邻卤代化。该转化是高度区域选择性的，并且观察到宽的底物范围和官能团耐受性。该发现对于酰胺，苯甲酸酯和其他具有引导基团的物质的选择性卤化可能具有重要意义。还介绍了机械研究。

  DOI：

  10.1039/c8nj06023a

文献信息

• A new air-stable Si,S-chelating ligand for Ir-catalyzed directed <i>ortho</i> C–H borylation
  作者：Jiao Jiao、Wenzheng Nie、Peidong Song、Pengfei Li

  DOI：10.1039/d0ob02335c

  日期：——

  reaction with a broad substrate scope. This study provides the first example of using a sulfur-containing ligand in the catalytic C–H borylation process. It provides a rapid, efficient, and economical method for the preparation of organoboron compounds.

  已开发出一种新型的空气稳定的Si，S螯合配体，并用于具有广泛底物范围的铱催化的邻位C-H硼酸酯化反应中。这项研究提供了在催化C–H硼化过程中使用含硫配体的第一个例子。它提供了一种快速，有效和经济的有机硼化合物的制备方法。
• Investigation of the Mechanism of C(sp³)−H Bond Cleavage in Pd(0)-Catalyzed Intramolecular Alkane Arylation Adjacent to Amides and Sulfonamides
  作者：Sophie Rousseaux、Serge I. Gorelsky、Benjamin K. W. Chung、Keith Fagnou

  DOI：10.1021/ja103081n

  日期：2010.8.11

  reactivity of C(sp(3))-H bonds adjacent to a nitrogen atom can be tuned to allow intramolecular alkane arylation under Pd(0) catalysis. Diminishing the Lewis basicity of the nitrogen lone pair is crucial for this catalytic activity. A range of N-methylamides and sulfonamides react exclusively at primary C(sp(3))-H bonds to afford the products of alkane arylation in good yields. The isolation of a Pd(II) reaction

  可以调整与氮原子相邻的 C(sp(3))-H 键的反应性，以允许在 Pd(0) 催化下进行分子内烷烃芳基化。降低氮孤对的路易斯碱度对于这种催化活性至关重要。一系列 N-甲基酰胺和磺酰胺仅在初级 C(sp(3))-H 键上反应，以高产率提供烷烃芳基化产物。Pd(II) 反应中间体的分离使得能够评估反应机理，重点是碱在 C(sp(3))-H 键断裂步骤中的作用。这些化学计量研究的结果，连同动力学同位素效应实验，为协调的金属化-去质子化 (CMD) 过渡态提供了罕见的实验支持，此前已在烷烃 C(sp(3))-H 芳基化中提出了这种过渡态。而且，DFT 计算揭示了新戊酸盐添加剂作为磷化氢从 Pd(II) 中间体解离的促进剂的额外作用，使 CMD 过渡态成为可能。最后，进行了动力学研究，揭示了反应速率表达及其与新戊酸盐浓度的关系。
• [EN] FUSED IMIDAZOLE DERIVATIVES AS IL-17 MODULATORS<br/>[FR] DÉRIVÉS D'IMIDAZOLE FUSIONNÉS UTILISÉS EN TANT QU'INHIBITEURS D'IL-17
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2019138017A1

  公开（公告）日：2019-07-18

  A series of substituted fused bicyclic imidazole derivatives, including benzimidazole derivatives and analogues thereof, being potent modulators of human IL-17 activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including inflammatory and autoimmune disorders.

  一系列替代的融合双环咪唑衍生物，包括苯并咪唑衍生物及其类似物，作为强效的人IL-17活性调节剂，因此在治疗和/或预防各种人类疾病，包括炎症性和自身免疫性疾病方面具有益处。
• 一种高效合成多取代2-吡啶酮类化合物的方法
  申请人：武汉大学

  公开号：CN111925320A

  公开（公告）日：2020-11-13

  本发明公开了一种高效合成多取代2‑吡啶酮类化合物的方法。该方法先将4‑碘‑2‑吡啶酮类化合物或者碘代尿嘧啶类化合物、亲电试剂(卤代烷烃或者溴代芳烃类化合物)、亲核试剂(烯烃、炔烃、硼酸酯等)、钯催化剂、降冰片烯衍生物、碱(碳酸钾)一起溶于有机溶剂(1,4‑二氧六环或者乙二醇二甲醚)中，然后在50～150℃下搅拌反应，反应后分离提纯，即可高效经济、绿色地合成多取代的2‑吡啶酮类与尿嘧啶类化合物。该方法条件温和，底物普适性好，产率高。所制备的2‑吡啶酮类与尿嘧啶类化合物广泛地应用在药物化学和有机化学领域。
• A Convenient Strategy for the Synthesis of 4,5-Bis(<i>o</i>-haloaryl)isoxazoles
  作者：Roberto Olivera、Raul SanMartin、Esther Domínguez、Xabier Solans、Miren Karmele Urtiaga、María Isabel Arriortua

  DOI：10.1021/jo0002700

  日期：2000.10.1

  synthesis of 4,5-bis(o-haloaryl)isoxazoles. Isolation of intermediate hydroxyisoxazolines, which are structurally examined, provides a definitive proof for a heterocyclization mechanism based on an amine exchange process. The isolation and X-ray crystallographic studies of significant side products such as benzamides and triarylpropionitriles are also described.

  可以有效地制备一系列新的1,2-双（邻卤代芳基）乙酮并将其应用于4,5-双（邻卤代芳基）异恶唑的合成。对中间体羟基异恶唑啉的分离进行了结构检查，为基于胺交换过程的杂环化机理提供了明确的证据。还描述了重要副产物（如苯甲酰胺和三芳基丙腈）的分离和X射线晶体学研究。