4-氯-N,N-二异丙基苯甲酰胺 | 79606-45-4

• 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-氯-N,N-二异丙基苯甲酰胺
• 英文名称: 4-chloro-N,N-diisopropylbenzamide
• 英文别名: N,N-diisopropyl 4-chlorobenzamide；N,N-diisopropyl-4-chlorobenzamide；p-chloro-N,N-diisopropylbenzamide；N,N-diisopropyl-p-chlorobenzamide；4-chloro-N,N-di(propan-2-yl)benzamide
• CAS: 79606-45-4
• 化学式: C₁₃H₁₈ClNO
• mdl: MFCD00032340
• 分子量: 239.745
• InChiKey: MGPPJDHMGGQMSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 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
• 储存条件：
  -20℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Chloro-N,N-diisopropylbenzamide
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.
4-Chloro-N,N-diisopropylbenzamide
Ingredient name:
CAS number: 79606-45-4

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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: C13H18ClNO
Molecular weight: 239.7

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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

制备方法与用途

OR59402和NSC 48107是一种生物活性化合物。

反应信息

• 作为反应物：
  描述：

  4-氯-N,N-二异丙基苯甲酰胺 在 盐酸 、 zinc(II) chloride 作用下， 反应 72.0h， 以100%的产率得到对氯苯甲酸
  参考文献：
  名称：

  一些苯甲酰胺的卤化优先发生在邻位、对位

  摘要：

  N, N-二取代苯甲酰胺在乙酸水溶液中的氯化和溴化方向受氮原子上烷基性质的强烈影响。对于大基团，卤化在邻/对位发生相当有选择性。

  DOI：

  10.1002/(sici)1099-0690(199808)1998:8<1689::aid-ejoc1689>3.0.co;2-m
• 作为产物：
  描述：

  对氯苯甲酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 4-氯-N,N-二异丙基苯甲酰胺
  参考文献：
  名称：

  通过两个 C-H 键的自由基介导的分子内偶联轻松合成异吲哚啉酮

  摘要：

  开发了一种通过自由基介导的 N,N-二异丙基苯甲酰胺的两个 C-H 键分子内偶联来构建 3,3-二甲基异吲哚啉酮的无金属方法。反应可以以中等到高产率进行，并具有出色的化学选择性。提出了通过烷基C-H键氧化裂解形成烷基自由基和通过分子内均裂芳族取代形成内酰胺环的反应顺序。

  DOI：

  10.1055/a-2043-4862

文献信息

• Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration
  作者：Noriyuki Tezuka、Kohei Shimojo、Keiichi Hirano、Shinsuke Komagawa、Kengo Yoshida、Chao Wang、Kazunori Miyamoto、Tatsuo Saito、Ryo Takita、Masanobu Uchiyama

  DOI：10.1021/jacs.6b03855

  日期：2016.7.27

  Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded

  芳族/杂芳族 CH 键的去质子定向邻铜化和随后用 t-BuOOH 氧化以高产率和高区域选择性和化学选择性提供官能化酚。DFT 计算表明，这种羟基化反应是通过铜 (I → III → I) 氧化还原机制进行的。将该反应应用于使用 BnONH2 的芳族 CH 胺化有效地提供了相应的伯苯胺。这些反应显示出广泛的范围和良好的官能团兼容性。还展示了这些转化的催化版本。
• Rhodium(III)-Catalyzed Direct CH Olefination of Arenes with Aliphatic Olefins
  作者：Xiao Xue、Jianbin Xu、Lingjuan Zhang、Conghui Xu、Yixiao Pan、Lijin Xu、Huanrong Li、Weidong Zhang

  DOI：10.1002/adsc.201500697

  日期：2016.2.18

  A rhodium(III)‐catalyzed direct ortho CH bond olefination of arenes, including but not limited to benzamides, arylpyridines and indoles, with a variety of unactivated aliphatic olefins has been developed. In the presence of catalytic amounts of dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer [Cp*RhCl2]2}, copper(II) acetate monohydrate [Cu(OAc)2⋅H2O] and silver hexafluoroantimonate(V) (AgSbF6)

  铑（III）催化的直接邻Ç 芳烃的H键烯，包括但不限于苯甲酰胺，芳基吡啶并吲哚，与各种未活化的脂族烯烃的已经研制成功。在催化量的二氯（五甲基环戊二烯）合铑（III）二聚体的[Cp *的RhCl存在2 ] 2 }，铜（II）一水合乙酸[铜（OAC）2 ⋅H 2 O]和六氟锑酸银（V）（ AgSbF 6），偶联反应有效发生，得到邻位烯烃化的线性产物，具有良好的产率和优异的选择性，并具有较高的区域选择性和立体选择性，并且两个偶合伙伴中的一系列官能团均与反应条件兼容。该方案依赖于使用导向基团，并且添加AgSbF 6作为添加剂对于催化至关重要。这种新方法扩大了铑（III）催化的芳烃直接CH键烯化反应的范围，并提供了快速获得未活化烯烃有用的线性芳基化产物的途径。
• Lipshutz-type bis(amido)argentates for directed <i>ortho</i> argentation
  作者：Noriyuki Tezuka、Keiichi Hirano、Andrew J. Peel、Andrew E. H. Wheatley、Kazunori Miyamoto、Masanobu Uchiyama

  DOI：10.1039/c9sc06060j

  日期：——

  aromatic functionalization via unprecedented directed ortho argentation (DoAg). X-Ray crystallographic analysis showed that 3 takes a structure analogous to that of the corresponding Lipshutz cuprate. DoAg with this TMP-Ag-ate afforded multifunctional aromatics in high yields in processes that exhibited high chemoselectivity and compatibility with a wide range of functional groups. These included organometallics-

  双（酰胺基）银盐（TMP）2 Ag（CN）Li 2（3，TMP-Ag-酸盐; TMP = 2,2,6,6-四甲基哌啶子基）被设计为通过空前的定向原位化学键进行化学选择性芳族官能化的工具（D o Ag）。X射线晶体学分析表明3具有与相应的Lipshutz铜酸盐类似的结构。d Ø具有这种TMP-Ag-酸酯的Ag在具有高化学选择性和与各种官能团相容性的工艺中，以高收率提供了多官能芳烃。这些包括对有机金属和过渡金属敏感的取代基，例如甲酯，醛，乙烯基，碘，（三氟甲磺酰基）氧基和硝基。白蚁类药物与各种亲电试剂显示出良好的反应性。硫属元素（S，Se和Te）的安装和偶氮偶合反应也有效进行。
• Directed <i>ortho</i>-metalation–nucleophilic acyl substitution strategies in deep eutectic solvents: the organolithium base dictates the chemoselectivity
  作者：Simone Ghinato、Giuseppe Dilauro、Filippo Maria Perna、Vito Capriati、Marco Blangetti、Cristina Prandi

  DOI：10.1039/c9cc03927a

  日期：——

  Directed ortho metalation (DoM) or nucleophilic acyl substitution (SNAc) can be efficiently programmed on the same aromatic carboxylic acid amide, in a choline chloride-based eutectic mixture, by simply switching the nature of the organolithium reagent. Telescoped, one-pot ortho-lithiation/Suzuki–Miyaura cross-couplings have also been demonstrated for the first time in Deep Eutectic Solvents.

  定向邻位金属化（d Ò M）或亲核酰基取代（S Ñ AC）可以有效地设定为在同芳族羧酸酰胺，在基于氯化物胆碱共熔混合物，通过简单地切换有机锂试剂的性质。伸缩式单罐正锂化/铃木-宫浦交叉联结也已在深共晶溶剂中首次得到证明。
• Visible-Light-Induced, Base-Promoted Transition-Metal-Free Dehalogenation of Aryl Fluorides, Chlorides, Bromides, and Iodides
  作者：Ting-Hui Ding、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.orglett.0c00827

  日期：2020.4.17

  We report a simple and efficient visible-light-induced transition-metal-free hydrogenation of aryl halides. The combined visible light and base system is used to initiate the desired radical-mediated hydrogenation. A variety of aryl fluorides, chlorides, bromides, and iodides could be reduced to the corresponding (hetero)arenes with excellent yields under mild conditions. Various functional groups

  我们报告了简单有效的芳基卤化物的可见光诱导的无过渡金属氢化。可见光和碱的组合系统用于引发所需的自由基介导的氢化反应。在温和条件下，可以将多种芳基氟化物，氯化物，溴化物和碘化物还原成相应的（杂）芳烃。可以容忍各种官能团和其他杂环化合物。