N-叔丁基=4-甲氧基苯甲酰胺 | 19486-73-8

• 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-叔丁基=4-甲氧基苯甲酰胺
• 中文别名: N-叔丁基-4-甲氧基苯甲酰胺
• 英文名称: N-tert-butyl-4-methoxybenzamide
• 英文别名: N-tert.-Butyl-4-methoxy-benzamid；4-methoxy-N-(tert-butyl)benzamide
• CAS: 19486-73-8
• 化学式: C₁₂H₁₇NO₂
• mdl: MFCD00751505
• 分子量: 207.272
• InChiKey: JZHSACJKCPNPHW-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C
• 沸点：
  346.0±25.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
N-tert-Butyl-4-methoxybenzamide
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P302+P352: IF ON SKIN: Wash with soap and water
P321: Specific treatment (see on this label)
P405: Store locked up

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Section 3. Composition/information on ingredients.
N-tert-Butyl-4-methoxybenzamide
Ingredient name:
CAS number: 19486-73-8

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C12H17NO2
Molecular weight: 207.3

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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.

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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：

  N-叔丁基=4-甲氧基苯甲酰胺 在 samarium diiodide 、 水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以84%的产率得到4-甲氧基苄醇
  参考文献：
  名称：

  SmI 2 / H 2 O和SmI 2 / Amine / H 2 O促进的氨基酰胺（一级，二级，三级）经由氨基酮基自由基化学选择性还原为醇的机理研究

  摘要：

  碘化（II）-水和碘化sa（II）-水-胺配合物被认为是从酰胺和衍生物选择性生成氨基酮基的有价值的试剂。产生的氨基酮基自由基可以经历还原或还原环化途径，为（i）通过具有挑战性的N–C键断裂从酰胺直接合成醇和（ii）通过酰胺的极性反转合成含氮杂环提供了有力方法键。本报告介绍了碘化sa（II）-水和碘化sa（II）-水-胺介导的从芳族伯，仲和叔酰胺（苯甲酰胺）生成苄基氨基酮基自由基的机理研究。机理实验表明，还原的速率和选择性与水浓度和进行还原的酰胺类型密切相关。数据还表明，与通过单电子转移至未活化的脂族酰胺而生成的相应氨基酮基相比，在苯甲酰胺还原中生成的苄基氨基酮基自由基对α取代的电子效应的依赖性更大。但是，在空间影响方面几乎没有变化 数据还表明，与通过单电子转移至未活化的脂族酰胺而生成的相应氨基酮基相比，在苯甲酰胺还原中生成的苄基氨基酮基自由基对α取代的电子效应的依赖性更大。但是，在空间影响方面几乎没有变化

  DOI：

  10.1021/acs.joc.7b00372
• 作为产物：
  描述：

  N-(4-methoxybenzylidene)-2-methylpropan-2-amine 在 potassium tert-butylate 、 氯化铵 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 N-叔丁基=4-甲氧基苯甲酰胺
  参考文献：
  名称：

  碱诱导的一氧化氮环加合物的环还原：无需常规氧化剂即可将亚胺转化为仲酰胺和叔酰胺，将芳族醛转化为酸

  摘要：

  一系列取代的Δ的2 -1,2,4-恶二唑啉（4,5-二氢-1,2,4-恶二唑）12已经制备由氧化腈的1,3-偶极环加成到亚胺并且发现，当用KOBu t处理，进行环还原，得到腈和酰胺阴离子。它们可以被质子化以得到仲酰胺，或者可以用烷基卤原位处理，以中等至良好的总收率得到叔酰胺，尽管该反应仅限于在5-位具有芳族取代基的实例。通过将苯甲腈氧化物环加成到芳族醛上而形成的1,4,2-二恶唑15类似地经历环还原，从而允许直接转化为取代的苯甲酸或它们的甲酯。

  DOI：

  10.1039/p19960000747

文献信息

• Fe(ClO4)3·H2O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles
  作者：Min Ji、Chengliang Feng、Bin Yan、Guibo Yin、Junqing Chen

  DOI：10.1055/s-0037-1610658

  日期：2018.10

  An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with esters catalyzed by Fe(ClO4)3·H2O is described. Fe(ClO4)3·H2O is an economically efficient catalyst for the Ritter reaction under solvent-free conditions. Reactions of a range of esters (benzyl, sec-alkyl, and tert-butyl esters) with nitriles (primary, secondary, tertiary, and aryl nitriles) were

  描述了通过 Fe(ClO4)3·H2O 催化的腈与酯的 Ritter 反应高效且廉价地合成 N-取代酰胺。Fe(ClO4)3·H2O 是一种在无溶剂条件下进行 Ritter 反应的经济高效的催化剂。进行一系列酯（苄基、仲烷基和叔丁基酯）与腈（伯腈、仲腈、叔腈和芳基腈）的反应，以高产率至极好的产率提供相应的酰胺。
• Palladium-catalyzed oxidative coupling of arylboronic acid with isocyanide to form aromatic carboxylic acids
  作者：Zhen-Bang Chen、Kui Liu、Fang-Ling Zhang、Qing Yuan、Yong-Ming Zhu

  DOI：10.1039/c7ob01428g

  日期：——

  A valuable palladium-catalyzed oxidative coupling of aryl- and alkenyl borides with isocyanide for the synthesis of corresponding carboxylic acids has been developed. With wide substrate scopes and good functional group tolerance, this reaction offers corresponding carboxylic acids in moderate to excellent yields.

  已经开发了有价值的钯-芳基和烯基硼化物与异氰化物的钯催化的氧化偶联，用于合成相应的羧酸。具有宽的底物范围和良好的官能团耐受性，该反应以中等至优异的产率提供了相应的羧酸。
• An Efficient and Scalable Ritter Reaction for the Synthesis of <i>tert</i>-Butyl Amides
  作者：Jean C. Baum、Jacqueline E. Milne、Jerry A. Murry、Oliver R. Thiel

  DOI：10.1021/jo8024797

  日期：2009.3.6

  A scalable procedure for the conversion of nitriles to N-tert-butyl amides via the Ritter reaction was optimized employing tert-butyl acetate and acetic acid. The reaction has a broad scope for aromatic, alkyl, and α,β-unsaturated nitriles.

  用于腈向转换可扩展的过程ñ -叔丁基酰胺通过Ritter反应进行优化使用叔丁基乙酸酯和乙酸。该反应对于芳族，烷基和α，β-不饱和腈具有广泛的范围。
• Experimental and Theoretical Studies on Ru(II)-Catalyzed Oxidative C–H/C–H Coupling of Phenols with Aromatic Amides Using Air as Oxidant: Scope, Synthetic Applications, and Mechanistic Insights
  作者：Luoqiang Zhang、Lei Zhu、Yuming Zhang、Yudong Yang、Yimin Wu、Weixin Ma、Yu Lan、Jingsong You

  DOI：10.1021/acscatal.8b02816

  日期：2018.9.7

  synthesis of Palomid 529, a drug in development for the treatment of glioblastoma and neovascular age-related macular degeneration. With a combination of experimental and theoretical methods, we get more insight into the essential issues of strategy determining the reaction process. The stronger coordinating ability of 2-aryloxypyridine and the less steric hindrance of amide are pivotal to the high chemoselectivity

  我们在本文中说明了借助Zn（OTf）2的Ru（II）催化的酚与（杂）芳族酰胺的氧化邻位-C-H / C-H交叉偶联的双重螯合辅助策略。，可快速组装2'-羟基联苯-2-羧酸衍生物的丰富文库。该方案具有广泛的底物范围，优异的官能团耐受性，空气作为末端氧化剂，偶联剂的摩尔比低以及按比例放大的合成。特别是，该方法可以耐受更复杂的天然产物衍生物，从而为后期功能化提供了机会。该方案还被用作简明合成Palomid 529的关键步骤，Palomod 529是一种正在开发的用于治疗胶质母细胞瘤和新血管性年龄相关性黄斑变性的药物。结合实验和理论方法，我们对决定反应过程的策略的基本问题有更多的了解。2-芳氧基吡啶的较强的配位能力和酰胺的空间位阻较小，这是交叉偶联相对于均相偶联的高化学选择性的关键。第一个C–H键活化步骤发生在酰胺底物上，随后在2-芳氧基吡啶上的C–H键活化反应参与速率确定的步骤。
• Exploiting the Reactivity of Isocyanide: Coupling Reaction between Isocyanide and Toluene Derivatives Using the Isocyano Group as an N1 Synthon
  作者：Zhiqiang Liu、Xinglu Zhang、Jianxiong Li、Feng Li、Chunju Li、Xueshun Jia、Jian Li

  DOI：10.1021/acs.orglett.6b01928

  日期：2016.8.19

  An unusual oxidative coupling reaction of isocyanide and toluene derivatives using tetrabutylammonium iodide (TBAI) as a catalyst is disclosed. The experimental results and mechanistic study show that the isocyano group acts formally as an N1 synthon during the transformation, thus expanding the reactivity profile of isocyanide.

  公开了使用碘化四丁铵（TBAI）作为催化剂的异氰酸酯和甲苯衍生物的不寻常的氧化偶联反应。实验结果和机理研究表明，异氰酸酯基团在转化过程中正式作为N1合成子起作用，从而扩大了异氰酸酯的反应活性。