N-叔丁基-4-氯苯甲酰胺 | 42498-40-8

• 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-氯苯甲酰胺
• 英文名称: N-tert-butyl-4-chlorobenzamide
• 英文别名: N-t-Butyl-p-chlor-benzamid
• CAS: 42498-40-8
• 化学式: C₁₁H₁₄ClNO
• mdl: MFCD00461169
• 分子量: 211.691
• InChiKey: XOEWMCMXPCWIDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

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-chlorobenzamide
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-chlorobenzamide
Ingredient name:
CAS number: 42498-40-8

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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: C11H14ClNO
Molecular weight: 211.7

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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 chloride.

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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-氯苯甲酰胺 在 silver hexafluoroantimonate 、 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl 、 palladium diacetate 、 三氟乙酸 、 silver(l) oxide 、 sodium t-butanolate 、 三甲基乙酸 作用下， 以 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 60.0h， 生成 4-(9,9-dimethylacridin-10(9H)-yl)-2-(5-(9,9-dimethylacridin-10(9H)-yl)benzo[b]thiophen-2-yl)benzamide
  参考文献：
  名称：

  深入了解苯并噻吩 C3-芳基化的好氧氧化 C-H/C-H 偶联中的区域选择性控制：迈向结构非传统 OLED 材料

  摘要：

  通过偶联反应安装含（苯并）噻吩的联芳基化合物已成为设计光电材料的主要方法。不可否认，两种（杂）芳烃之间的 C-H/C-H 交叉偶联反应将是通向这些结构片段的捷径。虽然更可靠的交叉偶联技术已经成熟以提供 C2 芳基化（苯并）噻吩，但芳基化 C3 位的有效方法仍未开发。在这里，我们深入了解了决定这些交叉偶联反应的区域选择性转换的因素。X 射线晶体学分析为三氟甲磺酸盐在区域选择性脱芳构化和醋酸盐在碱辅助抗芳烃中的关键作用提供了确凿的证据。-β-去质子化重构化。涉及两种底物的中型脱芳环金属化加合物的首次分离和 X 射线表征为有氧氧化 Ar-H/Ar-H 交叉偶联反应提供了额外的见解。机械突破孵化了第一个例子，使苯并噻吩的 C-H/C-H 型 C3-芳基化成为可能。最后，该化学物质用于设计具有螺旋构象的蓝色发射热激活延迟荧光 (TADF) 材料，在 OLED 中表现出高达 25.4% 的最大外部量子效率。

  DOI：

  10.1021/jacs.1c11277
• 作为产物：
  描述：

  (p-chlorobenzylidene)(tert-butyl)amine 在 potassium permanganate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以62%的产率得到N-叔丁基-4-氯苯甲酰胺
  参考文献：
  名称：

  Larsen, Jan; Jorgensen, Karl Anker; Christensen, Dorthe, Journal of the Chemical Society. Perkin transactions I, 1991, # 5, p. 1187 - 1190

  摘要：

  DOI：

文献信息

• 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。
• Synthesis of Amides via Palladium-Catalyzed Amidation of Aryl Halides
  作者：Huanfeng Jiang、Bifu Liu、Yibiao Li、Azhong Wang、Huawen Huang

  DOI：10.1021/ol103081y

  日期：2011.3.4

  A new and efficient method for the synthesis of amides via palladium-catalyzed C−C coupling of aryl halides with isocyanides is reported, by which a series of amides were formed from readily available starting materials under mild conditions. This transformation could extend its use to the synthesis of natural products and significant pharmaceuticals.

  报道了通过钯催化的芳基卤化物与异氰酸酯的C-C偶联合成酰胺的一种新的有效方法，通过该方法在温和的条件下由易于获得的起始原料形成了一系列酰胺。这种转变可以将其用途扩展到天然产物和重要药物的合成。
• Carboxylate-Assisted Iridium-Catalyzed C−H Amination of Arenes with Biologically Relevant Alkyl Azides
  作者：Tao Zhang、Xuejiao Hu、Zhen Wang、Tiantian Yang、Hao Sun、Guigen Li、Hongjian Lu

  DOI：10.1002/chem.201504880

  日期：2016.2.24

  wide substrate scope is reported. Benzamides with electron‐donating and ‐withdrawing groups and linear, branched, and cyclic alkyl azides are all applicable. Cesium carboxylate is crucial for both reactivity and regioselectivity of the reactions. Many biologically relevant molecules, such as amino acid, peptide, steroid, sugar, and thymidine derivatives can be introduced to arenes with high yields and

  据报道，铱催化的芳烃CHH胺化具有广泛的底物范围。具有给电子和吸电子基团以及线性，支化和环状烷基叠氮化物的苯甲酰胺均适用。羧酸铯对于反应的反应性和区域选择性都至关重要。许多生物学上相关的分子，例如氨基酸，肽，类固醇，糖和胸苷衍生物，都可以高收率和100％手性保留率引入芳烃。
• Ruthenium-Catalyzed Direct CH Amidation of Arenes Including Weakly Coordinating Aromatic Ketones
  作者：Jiyu Kim、Jinwoo Kim、Sukbok Chang

  DOI：10.1002/chem.201301025

  日期：2013.6.3

  CH activation: The ruthenium‐catalyzed direct sp2 CH amidation of arenes by using sulfonyl azides as the amino source is presented (see scheme). A wide range of substrates were readily amidated including arenes bearing weakly coordinating groups. Synthetic utility of the thus obtained products was demonstrated in the preparation of biologically active heterocycles.

  Ç  ħ激活：所述的钌催化直接SP 2 ç  ħ酰胺化，通过使用叠氮化物磺酰作为氨基源被呈现（参见方案）的芳烃。各种基材容易酰胺化，包括带有弱配位基团的芳烃。由此获得的产物的合成效用在生物活性杂环的制备中得到证明。
• Iridium-catalyzed <i>ortho</i>-selective carbon–hydrogen amidation of benzamides with sulfonyl azides in ionic liquid
  作者：Lin-Yu Jiao、Zi-Hui Ning、Qian Hong、Xin-Hua Peng、Xiao-Mei Yin、Shanshan Liu、Huiyong Chen、Zhuo Li、Ming Sun、Xiao-Xun Ma

  DOI：10.1039/d0ra05527a

  日期：——

  An efficient and convenient iridium(III) catalyzed ortho-C–H bond amidation of weakly coordinating benzamides treated with readily available sulfonyl azides as the amino source has been described. In this transformation, ionic liquids represents an ideal reaction medium, giving rise to a broad range of amidation products under mild conditions in the open air. This protocol offers moderate to excellent

  已经描述了用容易获得的磺酰叠氮化物作为氨基源处理的弱配位苯甲酰胺的有效且方便的铱( III )催化邻-C-H键酰胺化。在这种转变中，离子液体代表了一种理想的反应介质，在温和的露天条件下可产生多种酰胺化产物。该协议提供中等至优异的化学产量、独特的区域选择性和良好的官能团耐受性。