3-溴-N-异丙基苯甲酰胺 | 35306-75-3

• 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: 3-溴-N-异丙基苯甲酰胺
• 英文名称: 3-bromobenzoic acid isopropylamide
• 英文别名: 3-bromo-N-isopropylbenzamide；m-bromo-N-isopropylbenzamide；m-bromobenzamide；3-bromo-N-isopropyl-benzamide；3-bromo-N-propan-2-ylbenzamide
• CAS: 35306-75-3
• 化学式: C₁₀H₁₂BrNO
• mdl: MFCD00779673
• 分子量: 242.115
• InChiKey: FRETYNHHZZBJMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromo-N-isopropylbenzamide
Synonyms:

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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: 3-Bromo-N-isopropylbenzamide
CAS number: 35306-75-3

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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: 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：

  3-溴-N-异丙基苯甲酰胺 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81%的产率得到间溴苯甲腈
  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：

  3-溴-N,N-二异丙基苯甲酰胺 在 盐酸 、 zinc(II) chloride 作用下， 反应 72.0h， 以90%的产率得到间溴苯甲酸
  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

文献信息

• 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。
• Electrochemical generation and reactions of acyloxytriphenylphosphonium ions
  作者：Hidenobu Ohmori、Hatsuo Maeda、Masayuki Kikuoka、Toshihide Maki、Masaichiro Masui

  DOI：10.1016/s0040-4020(01)87066-6

  日期：1991.1

  undivided cell, of Ph3P in the presence of a carboxylic acid in CH2Cl2 containing 2,6-lutidinium perchlorate as the supporting electrolyte was shown to generate the corresponding acyloxyphosphonium ion, Ph3P+-OCOR, which was converted in situ to esters, amides, and β-lactams under mild conditions.

  结果表明，在羧酸存在下的CH 2 Cl 2中，含高氯酸2,6-lut啶鎓作为辅助电解质的PH 3 P在不分隔的电池中恒流电解会生成相应的酰氧基phosph离子Ph 3 P + -OCOR，在温和条件下原位转化为酯，酰胺和β-内酰胺。
• Chemoselective Synthesis of α-Amino-α-cyanophosphonates by Reductive <i>Gem</i>-Cyanation–Phosphonylation of Secondary Amides
  作者：Ting-Ting Chen、Ai-E Wang、Pei-Qiang Huang

  DOI：10.1021/acs.orglett.9b01257

  日期：2019.5.17

  A novel approach to α-amino-α-cyanophosphonates has been developed. The method features a Tf2O-mediated reductive geminal cyanation/phosphonylation of secondary amides. Mild reaction conditions, high bond-forming efficiency, inexpensive readily available starting materials, and good to excellent yields with wide functional group compatibility constitute the main advantages of this method. The protocol

  已经开发出一种新的方法来制备α-氨基-α-氰基膦酸酯。该方法的特征在于Tf 2 O介导的仲酰胺还原性双氰胺氰基化/膦酰基化。温和的反应条件，高的键形成效率，廉价的易得原料以及具有宽泛的官能团相容性的良好至优异的收率构成了该方法的主要优点。该协议可以以克为单位运行。
• Enamines as Surrogates of Alkyl Carbanions for the Direct Conversion of Secondary Amides to α-Branched Ketones
  作者：Yong-Peng Liu、Shu-Ren Wang、Ting-Ting Chen、Cun-Cun Yu、Ai-E Wang、Pei-Qiang Huang

  DOI：10.1002/adsc.201801443

  日期：2019.3.5

  A direct transformation of secondary amides into α‐branched ketones with enamines as soft alkylation reagents was developed. In this reaction, enamines serve as surrogates of alkyl carbanions, rather than the conventional enolates equivalents in the Stork's reactions, which allowed for the easy introduction of alkyl groups with electrophilic functional groups. In the presence of 4 Å molecular sieves

  已开发了以烯胺作为软烷基化试剂将仲酰胺直接转化为α-支链酮的方法。在该反应中，烯胺充当烷基碳负离子的替代物，而不是Stork反应中的常规烯醇式等同物，从而可以轻松引入具有亲电官能团的烷基。在存在4Å分子筛的情况下，该方法可以扩展到仲酰胺与醛的单锅偶联以生成酮。
• Cross‐Coupling of Secondary Amides with Tertiary Amides: The Use of Tertiary Amides as Surrogates of Alkyl Carbanions for Ketone Synthesis
  作者：Shu‐Ren Wang、Pei‐Qiang Huang

  DOI：10.1002/cjoc.201900215

  日期：2019.9

  has been made in the field of direct transformation of amides, nevertheless, the condensation between two amides remains rare and restricted to homo‐coupling reactions. Herein, we report the cross‐coupling of secondary amides with tertiary amides, which provides a synthesis of ketones under mild conditions, and features the use of tertiary amides as surrogates of alkyl carbanions. The method relies on

  近年来，在酰胺的直接转化领域取得了令人兴奋的进展，尽管如此，两种酰胺之间的缩合仍然很少，并且仅限于均偶联反应。本文中，我们报道了仲酰胺与叔酰胺的交叉偶联，这可在温和条件下提供酮的合成，并具有使用叔酰胺作为烷基碳负离子的替代物的功能。该方法依赖于由叔酰胺通过用Vaska催化剂催化部分还原叔酰胺而产生的烯胺与由仲酰胺通过三氟甲磺酸酐活化而原位形成的腈离子的偶联，以及随后的甲酰化作用。