N-丁基-2-溴苯甲酰胺 | 349403-39-0

• 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-丁基-2-溴苯甲酰胺
• 中文别名: 2-溴-n-丁基苯甲酰胺
• 英文名称: 2-bromo-N-butylbenzamide
• CAS: 349403-39-0
• 化学式: C₁₁H₁₄BrNO
• mdl: MFCD01212979
• 分子量: 256.142
• InChiKey: PVEIQVRGXQHPBG-UHFFFAOYSA-N

物化性质

• 沸点：
  355.7±25.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)
• 保留指数：
  1905

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 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
Product Name: N-Butyl 2-bromobenzamide
Synonyms: 2-Bromo-N-butylbenzamide

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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: N-Butyl 2-bromobenzamide
CAS number: 349403-39-0

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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: C11H14BrNO
Molecular weight: 256.1

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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-丁基-2-溴苯甲酰胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 2,2'-联吡啶 、 copper(l) iodide 、 potassium carbonate 、 吡啶 、 甲氧基胺盐酸盐 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 27.0h， 以82%的产率得到2-丁基-1,2-苯并异噻唑啉-3-酮
  参考文献：
  名称：

  铜催化条件下由2-溴苯甲酰胺和硫制备苯并异噻唑酮

  摘要：

  已经开发了一种方便的两步法，用于在铜催化条件下通过一锅法从2-溴苯甲酰胺和硫制备苯并[ d ]异噻唑-3（2 H）-一。该方法适合于合成N-芳基-，苄基-和烷基取代的苯并异噻唑酮。苯并异噻唑酮的产率取决于起始酰胺的性质，可以达到91％。

  DOI：

  10.1007/s10593-013-1193-5
• 作为产物：
  描述：

  N-丁基苯甲酰胺 在 N-溴代丁二酰亚胺(NBS) 、 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 三甲基乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以80%的产率得到N-丁基-2-溴苯甲酰胺
  参考文献：
  名称：

  High-Yielding, Versatile, and Practical [Rh(III)Cp*]-CatalyzedOrthoBromination and Iodination of Arenes

  摘要：

  We report a uniquely high-yielding, general, and practical ortho bromination and iodination reaction of different classes of aromatic compounds. This reaction occurs by Rh(III)-catalyzed C-H bond activation methodology and is therefore the first example of the application of this cationic catalyst for C-Br and C-I bond formation.

  DOI：

  10.1021/ja302631j

文献信息

• Convenient metal-free direct oxidative amidation of aldehyde using dibromoisocyanuric acid under mild conditions
  作者：Soosung Kang、Minh Thanh La、Hee-Kwon Kim

  DOI：10.1016/j.tetlet.2018.08.026

  日期：2018.9

  synthesized by an oxidative amidation in the presence of dibromoisocyanuric acid (DBI). Treatment of aromatic and aliphatic aldehydes with dibromoisocyanuric acid generated acyl bromide intermediates, which were employed to react with a variety of secondary and primary amines to give amides. Through this reaction method, various amides were synthesized directly from aldehydes under mild conditions in high yields

  描述了一种从醛直接合成酰胺的简便方法。在二溴异氰尿酸（DBI）存在下，通过氧化酰胺化合成酰胺键。用二溴异氰尿酸处理芳族和脂族醛可生成酰基溴中间体，该中间体可与多种仲胺和伯胺反应生成酰胺。通过这种反应方法，可以在温和的条件下以高收率和短时间直接从醛中合成出各种酰胺。这种简便有效的方法为从醛直接合成酰胺提供了潜在的策略。
• Synthesis of 1-Aminoisoquinolines by Gold(III)-Mediated Domino Reactions from 2-Alkynylbenzamides and Ammonium Acetate
  作者：Yuhua Long、Zhigang She、Xiaochen Liu、Yu Chen

  DOI：10.1021/jo302794z

  日期：2013.3.15

  1-aminoisoquinoline derivatives by gold(III)-mediated domino reactions is described. This synthetic protocol starts from readily available 2-alkynylbenzamides and ammonium acetate and takes place under mild reaction conditions compatible with a variety of functional groups. A plausible mechanism for the domino process is proposed, supported by the reaction of a possible intermediate, N-(3-phenyl-1H-isochrom

  描述了一种通过金（III）介导的多米诺反应向药学上感兴趣的1-氨基异喹啉衍生物的简便合成路线。该合成方案从容易获得的2-炔基苯甲酰胺和乙酸铵开始，并且在与各种官能团相容的温和反应条件下进行。提出了一种可行的多米诺骨牌机制，并由一种可能的中间体N-（3-苯基-1H-异色烯-1-亚烷基）丙-1-胺的反应所支持。
• N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines
  作者：Anitha Alanthadka、C. Uma Maheswari

  DOI：10.1002/adsc.201400739

  日期：2015.4.13

  (NHC)‐catalyzed oxidative amidation of aromatic aldehydes with amines in the presence of N‐bromosuccinimide (NBS) as an oxidant has been developed for the synthesis of amides. This amidation strategy is tolerant to both the electronic and the steric nature of the aryl aldehydes employed. The present methodology was extended to chiral amino acid derivatives to generate the corresponding amides in good

  在N-溴代琥珀酰亚胺（NBS）作为氧化剂的存在下，已开发出N-杂环卡宾（NHC）催化的芳香族醛与胺的氧化酰胺化反应，用于合成酰胺。该酰胺化策略对所用芳基醛的电子和空间位阻均是耐受的。本方法学扩展到手性氨基酸衍生物，以高收率和优异的ee值（> 98％）生成相应的酰胺。
• Synthesis of 3-Substituted Isocoumarin Derivatives via CuI-Catalyzed Reaction of o-Bromobenzamides with 1,3-Diketones
  作者：Chanjuan Xi、Shangjun Cai、Fei Wang

  DOI：10.1055/s-0031-1290949

  日期：2012.6

  Abstract An approach to a variety of 3-substituted isocoumarins has been developed. The reaction proceeded from o-bromobenz­amide derivatives and 1,3-diketones via CuI-catalyzed reaction in DMF under the action of K3PO4 at 120 °C without ligands or additives. An approach to a variety of 3-substituted isocoumarins has been developed. The reaction proceeded from o-bromobenz­amide derivatives and 1,3-diketones

  摘要 已经开发出一种用于多种3-取代的异香豆素的方法。该反应由邻溴苯甲酰胺衍生物和1,3-二酮在K 3 PO 4的作用下于120°C下在DMF中经CuI催化的反应在没有配体或添加剂的情况下进行。 已经开发出一种用于多种3-取代的异香豆素的方法。该反应由邻溴苯甲酰胺衍生物和1,3-二酮在K 3 PO 4的作用下于120°C下在DMF中经CuI催化的反应在没有配体或添加剂的情况下进行。
• Synthesis of pyrimido[2,1-<i>a</i>]isoindolone and isoindolo[2,1-<i>a</i>]quinazolinone <i>via</i> intramolecular aza-Prins type reaction
  作者：Subhamoy Biswas、Bikoshita Porashar、Pallav Jyoti Arandhara、Anil K. Saikia

  DOI：10.1039/d1cc04554g

  日期：——

  A novel aza-Prins type cyclization reaction involving N-acyliminium ions and amides is reported for the synthesis of tetrahydropyrimido[2,1-a]isoindole-2,6-dione and 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives in excellent yields. The strategy features inexpensive reagents, mild reaction conditions, and metal-free synthesis of N-heterocyclic frameworks. Further, post-synthetic modification

  涉及一种新颖氮杂普林斯型环化反应Ñ -acyliminium离子和酰胺被报告四氢嘧啶并[2,1-的合成一个]异吲哚-2,6-二酮和6,6-一个-dihydroisoindolo [2,1-一个]喹唑啉-5,11-二酮衍生物，产率极好。该策略的特点是试剂价格低廉，反应条件温和，N-杂环骨架的无金属合成。此外，合成后的修饰导致其前所未有的三唑、四环二氮杂环戊二烯[ def ]菲-1,4(9 a 1 H )-二酮和羰基衍生物的形成。