N-异丙基-4-溴苯甲酰胺 | 336182-29-7

• 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-异丙基-4-溴苯甲酰胺
• 中文别名: 4-溴-N-异丙基苯甲酰胺
• 英文名称: 4-bromo-N-isopropylbenzamide
• 英文别名: 4-bromo-N-propan-2-ylbenzamide
• CAS: 336182-29-7
• 化学式: C₁₀H₁₂BrNO
• mdl: MFCD00465197
• 分子量: 242.115
• InChiKey: PWXNCWKINUCUPV-UHFFFAOYSA-N

物化性质

• 沸点：
  344.6±25.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 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,P301+P312,P302+P352,P304+P340,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-Isopropyl 4-bromobenzamide
Synonyms: 4-Bromo-N-isopropylbenzamide

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H412: Harmful to aquatic life with long lasting effects
P273: Avoid release to the environment

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Section 3. Composition/information on ingredients.
Ingredient name: N-Isopropyl 4-bromobenzamide
CAS number: 336182-29-7

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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.
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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H12BrNO
Molecular weight: 242.1

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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：

  N-异丙基-4-溴苯甲酰胺 在 2-氟吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以80%的产率得到4-溴苯腈
  参考文献：
  名称：

  脂族和芳族仲酰胺向腈的多功能和化学选择性转化

  摘要：

  三氟甲磺酸酐与2-氟吡啶结合可有效地使仲酰胺脱水，在温和的反应条件下提供腈。该反应是一般性的，并且与带有仲，叔或苄基N-烷基的脂族，α，β-不饱和，芳族和杂芳族酰胺的使用相容。该反应还显示出对仲酰胺的良好的化学选择性至优异的化学选择性，并能耐受几个不稳定的官能团。

  DOI：

  10.1016/j.tet.2015.03.094
• 作为产物：
  描述：

  4-溴苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 生成 N-异丙基-4-溴苯甲酰胺
  参考文献：
  名称：

  [EN] FUNCTIONALISED AND SUBSTITUTED INDOLES AS ANTI-CANCER AGENTS
  [FR] INDOLES FONCTIONNALISÉS ET SUBSTITUÉS UTILISÉS EN TANT QU'AGENTS ANTI-CANCÉREUX

  摘要：

  本发明涉及抗肌球蛋白化合物，其制备方法，以及利用本发明的化合物治疗或预防增殖性疾病，优选癌症的方法。

  公开号：

  WO2015074123A1

文献信息

• Isoquinoline-Catalyzed Reaction of Phenacyl Bromide and N,N-Dialkyl­carbodiimides: Novel Synthesis of Azirines
  作者：Abdolali Alizadeh、Atieh Rezvanian

  DOI：10.1055/s-0031-1290487

  日期：2012.4

  A practical and efficient procedure for the synthesis of polysubstituted azirines and in some cases benzamides was developed through reaction of phenacyl bromides and N,N-dialkylcarbodiimides, in the presence of catalytic amount of isoquinoline in dry acetonitrile under mild conditions at ambient temperature. The salient features of this process include operational simplicity, high yields, and easily

  在室温温和条件下，在催化量的异喹啉的干燥乙腈中，通过苯甲酰溴和 N,N-二烷基碳二亚胺的反应开发了一种实用且有效的合成多取代氮丙啶类化合物和在某些情况下苯甲酰胺的方法。该过程的显着特点包括操作简单、产量高和易于获得起始材料。
• Ketone Synthesis by Direct, Orthogonal Chemoselective Hydroacylation of Alkenes with Amides: Use of Alkenes as Surrogates of Alkyl Carbanions
  作者：Hui Geng、Pei‐Qiang Huang

  DOI：10.1002/cjoc.201900252

  日期：2019.8

  and direct transformation of carboxamides are two exciting areas that have attracted considerable attention in recent years. We report herein that secondary amides, the least reactive derivatives of carbonyl compounds, upon activated with triflic anhydride, can serve as effective hydroacylating reagents in partner with alkenes to yield ketones at ambient temperature. The method was applied to the one‐step

  烯烃的直接官能化和羧酰胺的直接转化是近年来令人瞩目的两个令人兴奋的领域。我们在此报道，仲酰胺，即羰基化合物的反应性最低的衍生物，在用三氟甲磺酸酐活化后，可以与烯烃一起作为有效的氢酰化试剂，在环境温度下产生酮。该方法已用于外消旋二氢芳基羟色酮的一步合成。在这种方法中，烯烃用作有机金属试剂的替代物，从而可以进行正交的化学选择性反应。许多烯烃（如camp烯和降冰片烯）的现成性允许一步合成酮，而传统方法则需要几个步骤。
• [EN] AZETIDINYL PHENYL, PYRIDYL OR PYRAZINYL CARBOXAMIDE DERIVATIVES AS JAK INHIBITORS<br/>[FR] DÉRIVÉS D'AZÉTIDINYL-PHÉNYL-, DE PYRIDYL- OU DE PYRAZINYL-CARBOXAMIDE EN TANT QU'INHIBITEURS DES JAK
  申请人：INCYTE CORP

  公开号：WO2012177606A1

  公开（公告）日：2012-12-27

  The present invention provides azetidinyl phenyl, pyridyl, or pyrazinyl carboxamide derivatives of formula (I), as well as their compositions and methods of use, that modulate the activity of Janus kinase (JAKs) and are useful in the treatment of diseases related to the activity of JAK including, for example, inflammatory disorders, autoimmune disorders, cancer, and other diseases.

  本发明提供了式(I)的氮杂环丙基苯基、吡啶基或吡嗪基羧酰胺衍生物，以及它们的组合物和使用方法，这些衍生物调节Janus激酶（JAKs）的活性，并且在治疗与JAK活性相关的疾病方面具有用处，例如炎症性疾病、自身免疫性疾病、癌症和其他疾病。
• Syntheses of amides via iodine-catalyzed multiple sp3 C-H bonds oxidation of methylarenes and sequential coupling with N,N-dialkylformamides
  作者：BingNan Du、PeiPei Sun

  DOI：10.1007/s11426-014-5098-7

  日期：2014.8

  The oxidative coupling of methylarenes and N,N-dialkylformamides was developed, and the appropriate reaction conditions were established. By using I2 as the catalyst, and tert-butyl hydroperoxide (TBHP) as the oxidant, the reaction provided N,N-dialkylamides or N-alkylamides with moderate yields via multiple sp3 C-H bonds activation of methylarenes in aqueous and metal-free conditions.

  建立了甲基芳烃与N，N-二烷基甲酰胺的氧化偶联反应，并建立了适当的反应条件。通过使用I 2作为催化剂，使用叔丁基过氧化氢（TBHP）作为氧化剂，该反应通过多个sp 3 CH键提供了中等收率的N，N-二烷基酰胺或N-烷基酰胺，可以在含水和无金属条件下活化甲基芳烃条件。
• Mild Metal-Free Hydrosilylation of Secondary Amides to Amines
  作者：Pei-Qiang Huang、Qi-Wei Lang、Yan-Rong Wang

  DOI：10.1021/acs.joc.6b00572

  日期：2016.5.20

  tetrahydro-5-oxo-2-furaneamides yielded 5-(aminomethyl)dihydrofuran-2(3H)-ones in a racemization-free manner. The latter were converted in one pot to N-protected 5-hydroxypiperidin-2-ones, which are building blocks for the synthesis of many natural products. Further elaboration of an intermediate led to a concise four-step synthesis of (−)-epi-pseudoconhydrine.

  Tf 2 O的酰胺活化与B（C 6 F 5）3催化的氢硅烷基化与TMDS的结合构成了一种在温和条件下将一阶仲酰胺还原为胺的方法。该方法对减少多种类型的底物显示出广泛的适用性，并且对于许多敏感的官能团显示出良好的相容性和优异的化学选择性。从另一种合成方法获得的多官能化的α，β-不饱和酰胺的还原以及C–H官能化的产物可产生相应的胺，收率好至极好。化学选择性还原对映体纯的（ee> 99％）四氢-5-氧代-2-呋喃酰胺，生成5-（氨基甲基）二氢呋喃-2（3 H）-以无消旋的方式进行。将后者在一个罐中转化为N保护的5-羟基哌啶-2-酮，这是合成许多天然产物的基础。进一步精制中间体导致（-）- Epi- pseudoconhydrine的简洁的四步合成。