2-氨基-4-溴苯腈 | 304858-65-9

• 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: 2-氨基-4-溴苯腈
• 中文别名: 2-氨基-4-溴苯甲腈
• 英文名称: 2-amino-4-bromobenzonitrile
• CAS: 304858-65-9
• 化学式: C₇H₅BrN₂
• mdl: MFCD08752638
• 分子量: 197.034
• InChiKey: PWJBXJQMHYIRKI-UHFFFAOYSA-N

物化性质

• 沸点：
  317.8±27.0 °C(Predicted)
• 密度：
  1.69

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• TSCA：
  N
• 危险等级：
  IRRITANT
• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Amino-4-bromobenzonitrile
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-4-bromobenzonitrile
CAS number: 304858-65-9

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C7H5BrN2
Molecular weight: 197

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氨基-4-溴苯腈 在 三氟乙酸 、 双氧水 作用下， 反应 2.67h， 以70%的产率得到2-硝基-4-溴苯腈
  参考文献：
  名称：

  Synthesis and Dual D₂ and 5-HT_1A Receptor Binding Affinities of 7-piperazinyl and 7-piperidinyl-3,4-dihydroquinazolin-2(1H)-ones

  摘要：

  一系列新的7-哌嗪基和7-哌啶基-3,4-二氢喹唑啉-2(1H)-酮已被合成。所述化合物在结构上与阿多拉嗪相关，后者是一种潜在的不典型抗精神病药物，具有强效的D2受体拮抗剂和5-HT1A受体激动剂特性。制备了适当修饰的芳基溴化物，并与叔丁基哌嗪-1-羧酸酯缩合，得到高级中间体哌嗪基-3,4-二氢喹唑啉-2(1H)-酮。同样，Suzuki-Miyaura交叉偶联反应中，环状乙烯基硼酸盐与适当的芳基溴化物反应，得到哌啶基-3,4-二氢喹唑啉-2(1H)-酮。通过哌嗪基和哌啶基-3,4-二氢喹唑啉-2(1H)-酮与适当设计的联芳基醛的还原胺化反应，完成了这些目标化合物的合成。所述化合物被筛选为D2和5-HT1A受体结合亲和力。结构-活性关系研究表明，环戊烯基吡啶和环戊烯基苄基对这些化合物的双重D2和5-HT1A受体结合亲和力有显著贡献。

  DOI：

  10.2174/15734064113096660046
• 作为产物：
  描述：

  2-氨基苯甲腈 在 N-溴代丁二酰亚胺(NBS) 、 lithium perchlorate 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以95%的产率得到2-氨基-4-溴苯腈
  参考文献：
  名称：

  高氯酸锂分散在硅胶上在N-溴代琥珀酰亚胺溴化芳香族化合物中的有趣作用

  摘要：

  通过在室温下将 N-溴代琥珀酰亚胺和芳族化合物在二氧化硅表面混合，开发了一种方便有效的亲电芳族溴化方法。

  DOI：

  10.1139/v05-001

文献信息

• The Cascade Methylation/Cyclization of <i>ortho</i> -Cyanoarylacrylamides with Dicumyl Peroxide
  作者：Tao Yang、Wen-Jin Xia、Bin Zhou、Yangchun Xin、Yuehai Shen、Ya-Min Li

  DOI：10.1002/ejoc.201900918

  日期：2019.9.8

  A radical cascade methylation/cyclization of ortho‐cyanoarylacrylamides was developed by utilizing dicumyl peroxide as a methylation reagent. This transformation provides a simple and straightforward approach to methylated quinoline‐2,4(1H,3H)‐diones, and exhibits a wide substrate scope. Furthermore, this reaction could be readily scaled up.

  通过使用过氧化二枯基作为甲基化试剂，开发了邻-氰基芳基丙烯酰胺的自由基级联甲基化/环化反应。这种转化为甲基化喹啉-2,4（1 H，3 H）-二酮提供了一种简单明了的方法，并具有广泛的底物范围。此外，该反应可以容易地扩大规模。
• [EN] DIHYDROBENZOFURAN DERIVATIVES AS INSECTICIDAL COMPOUNDS<br/>[FR] DÉRIVÉS DE DIHYDROBENZOFURANE UTILISABLES EN TANT QUE COMPOSÉS INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2014135095A1

  公开（公告）日：2014-09-12

  Provided are compounds of formula (I) and methods of controlling insects, acarines, nematodes or molluscs, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I).

  提供的是公式(I)的化合物以及控制昆虫、蜱虫、线虫或软体动物的方法，该方法包括将公式(I)的化合物的杀虫剂、杀蜱剂、杀线虫剂或杀软体动物剂有效量的化合物应用于害虫、害虫的栖息地或易受害虫侵害的植物上。
• Chemoselective Double Annulation of Two Different Isocyanides: Rapid Access to Trifluoromethylated Indole-Fused Heterocycles
  作者：Yuelei Gao、Zhongyan Hu、Jinhuan Dong、Jun Liu、Xianxiu Xu

  DOI：10.1021/acs.orglett.7b02582

  日期：2017.10.6

  chemoselective double annulation of α-trifluoromethylated isocyanides with o-acylaryl isocyanides has been developed. This new reaction provides a rapid, efficient, and complete atom-economic strategy for the synthesis of trifluoromethylated oxadiazino[3,2-a]indoles in a single operation from readily available starting materials. Isocyanide insertion into C═O double bonds is disclosed for the first

  已经开发出空前的α-三氟甲基化异氰酸酯与邻酰基芳基异氰酸酯的化学选择性双环。该新反应提供了快速，有效和完整的原子经济策略，可通过一次操作从容易获得的起始原料合成三氟甲基化的恶二嗪并[3,2- a ]吲哚。由18 O-标记实验的结果表明，异氰酸酯首次插入C = O双键。提出了这种多米诺反应的机制，其中包括两种不同异氰酸酯的化学选择性异二聚化，然后是吲哚-2,3-环氧化物的形成和重排。
• Linear-Organic-Polymer-Supported Iridium Complex as a Recyclable Auto-Tandem Catalyst for the Synthesis of Quinazolinones via Selective Hydration/Acceptorless Dehydrogenative Coupling from <i>o</i>-Aminobenzonitriles
  作者：Shushu Hao、Jiazhi Yang、Peng Liu、Jing Xu、Chenchen Yang、Feng Li

  DOI：10.1021/acs.orglett.1c00475

  日期：2021.4.2

  coordinative immobilization of [Cp*IrCl2]2 on poly(4-vinylpyridine), was proven to be an efficient heterogeneous autotandem catalyst for synthesizing quinazolinones via selective hydration/acceptorless dehydrogenative coupling from o-aminobenzonitriles. Furthermore, the synthesized catalyst was recycled five times without an obvious decrease in the catalytic activity.

  通过将[Cp * IrCl 2 ] 2配位固定在聚（4-乙烯基吡啶）上设计和合成的线性有机聚合物负载的铱络合物Cp * Ir @ P4VP被证明是一种有效的异质串联催化剂通过邻氨基苄腈的选择性水合/无受体脱氢偶联合成喹唑啉酮。此外，将合成的催化剂循环使用五次，而催化活性没有明显降低。
• Quinazolinones from <i>o</i> -Aminobenzonitriles by One-Pot Sequential Selective Hydration/Condensation/Acceptorless Dehydrogenation Catalyzed by an Iridium Complex
  作者：Wei Zhao、Pengcheng Liu、Feng Li

  DOI：10.1002/cctc.201501385

  日期：2016.4.20

  A new strategy for the direct synthesis of quinazolinones from o‐aminobenzonitriles was proposed and accomplished. In the presence of [Cp*IrCl2]2 (Cp*=pentamethylcyclopentadienyl), a variety of desirable products was obtained easily through the one‐pot sequential selective hydration/condensation/acceptorless dehydrogenation. This protocol is highly attractive because it uses readily available starting

  提出并完成了由邻氨基苯甲腈直接合成喹唑啉酮的新策略。在[Cp * IrCl 2 ] 2（Cp * =五甲基环戊二烯基）的存在下，通过一锅顺序选择性水合/缩合/无受体脱氢可以轻松获得各种所需产物。该协议具有很高的吸引力，因为它使用了容易获得的起始原料，原子效率高，产率高到优，化学药品和能源的消耗最少。值得注意的是，这项研究显示出开发涉及无受体脱氢的过渡金属催化单锅顺序反应的新潜力。