4,5-二溴-1H-咪唑 | 2302-30-9

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 4,5-二溴-1H-咪唑
• 中文别名: 4,5-二溴咪唑；4,5-二碘-1H-咪唑
• 英文名称: 4,5-dibromo-1H-imidazole
• 英文别名: 4,5-dibromo-imidazole；4,5-dibromoimidazole；4,5-dibromo-1H-imidazole；4,5-Dibrom-1H-imidazol
• CAS: 2302-30-9
• 化学式: C₃H₂Br₂N₂
• 分子量: 225.87
• InChiKey: MYYYOBVDIRECDX-UHFFFAOYSA-N

物化性质

• 熔点：
  214-216°C
• 沸点：
  388.6±22.0 °C(Predicted)
• 密度：
  2.419

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  7
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R20/21/22
• 海关编码：
  2933290090
• 安全说明：
  S26,S36/37/39
• 包装等级：
  II
• 危险类别：
  6.1,8
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P310,P302+P352,P304+P340,P305+P351+P338,P310,P321,P330,P332+P313,P362,P403+P233,P405,P501
• 危险品运输编号：
  2928
• 危险性描述：
  H301,H315,H318,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4,5-Dibromo-1H-imidazole
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: 4,5-Dibromo-1H-imidazole
CAS number: 2302-30-9

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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: C3H2Br2N2
Molecular weight: 225.9

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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：

  4,5-二溴-1H-咪唑 在 sodium sulfite 作用下， 以 水 、 异丙醇 为溶剂， 以3.6 kg的产率得到4-溴-1H-咪唑
  参考文献：
  名称：

  一种4-卤素-1H-咪唑的制备方法

  摘要：

  本发明公开了一种4‑卤素‑1H‑咪唑的制备方法，包括如下步骤：(1)以咪唑和卤素单质为原料，在碱性条件下60‑100℃反应，反应结束后过滤，所得滤饼为4‑卤素‑1H‑咪唑粗品；(2)4‑卤素‑1H‑咪唑粗品与还原剂进行还原反应，反应结束，冷却，过滤，滤饼经萃取、减压浓缩后得4‑卤素‑1H‑咪唑纯品。本发明工艺简单，反应收率高，成本低，零污染，没有废液排放。

  公开号：

  CN106674121A
• 作为产物：
  描述：

  2,4,5-三溴咪唑 在 盐酸 、 乙基溴化镁 作用下， 生成 4,5-二溴-1H-咪唑
  参考文献：
  名称：

  方便合成4（5）-单-，4,5-二-和2,4,5-三取代的咪唑

  摘要：

  描述了一种通过卤素-金属交换技术，通过FGI将2-被保护的2,4,5-三溴咪唑中的溴原子按2→5→4的顺序逐步引入取代基（包括氢）到咪唑环中的方法。

  DOI：

  10.1016/s0040-4039(00)84334-8

文献信息

• “Fleximers”. Design and Synthesis of a New Class of Novel Shape-Modified Nucleosides¹
  作者：Katherine L. Seley、Liang Zhang、Asmerom Hagos、Stephen Quirk

  DOI：10.1021/jo0255476

  日期：2002.5.1

  A new class of shape-modified nucleosides is introduced. These novel "fleximers" feature the purine ring systems of adenosine, inosine, and guanosine split into their individual imidazole and pyrimidine components (as in 1-3). This structural modification serves to introduce flexibility into the nucleoside while still retaining the elements essential for recognition. As a consequence, these novel fleximers

  引入了一类新的形状修饰的核苷。这些新颖的“挠性分子”具有腺嘌呤，肌苷和鸟苷的嘌呤环系统，分为各自的咪唑和嘧啶组分（如1-3所示）。这种结构修饰用于将柔韧性引入核苷，同时仍保留识别所必需的元素。结果，这些新颖的挠性基团应该被用作研究探针-辅酶结合位点以及核酸和蛋白质相互作用的生物探针。描述了它们的设计和综合。
• “Fleximers”. Design and Synthesis of Two Novel Split Nucleosides
  作者：Katherine L. Seley、Liang Zhang、Asmerom Hagos

  DOI：10.1021/ol0165443

  日期：2001.10.1

  shape-modified nucleosides is introduced. The purine heterobases of adenosine and guanosine have been split into their imidazole and pyrimidine components, thereby introducing flexibility while retaining the elements necessary for recognition. As a consequence, these novel "fleximers" should find use as bioprobes for investigating enzyme-coenzyme binding sites as well as nucleic acid and protein interactions

  [结构：见正文]引入了一类新的形状修饰的核苷。腺苷和鸟嘌呤的嘌呤杂碱基已被拆分成咪唑和嘧啶成分，从而在保持识别所需元素的同时引入了灵活性。结果，这些新颖的“挠性分子”应被用作研究酶-辅酶结合位点以及核酸和蛋白质相互作用的生物探针。描述了它们的设计和综合。
• TGF-Beta Inhibitors
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：US20160257690A1

  公开（公告）日：2016-09-08

  Disclosed are imidazole and thiazole compounds, as well as pharmaceutical compositions and methods of use thereof. One embodiment is a compound having the structure and pharmaceutically acceptable salts, prodrugs and N-oxides thereof (and solvates and hydrates thereof), wherein X, A, Z, R 1 and R′ are as described herein. In certain embodiments, a compound disclosed herein inhibits TGF-β, and can be used to treat disease by blocking TGF-β signaling.

  本文披露了咪唑和噻唑化合物，以及其药物组合物和使用方法。一个实施例是具有以下结构的化合物 及其药用可接受盐、前药和N-氧化物（以及其溶剂和水合物），其中X、A、Z、R1和R'如本文所述。在某些实施例中，本文披露的化合物抑制TGF-β，并可用于通过阻断TGF-β信号传导来治疗疾病。
• Use of the vinyl group as an efficient protecting group for azole N- atoms: Synthesis of polyfunctionalized imidazoles and thieno[2,3-d] ⇌ [3,2-d]imidazole
  作者：David J. Hartley、Brian Iddon

  DOI：10.1016/s0040-4039(97)00957-x

  日期：1997.6

  2 → 5 → 4 via Br → MgBr and other exchange reactions. Efficient removal of the vinyl groups from the resulting polyfunctionalized imidazoles was achieved with ozone or potassium permanganate. An extension of this methodology has allowed the first synthesis of thieno[2,3-d] ⇌ [3,2-d]-imidazole.

  由2,4,5-三溴咪唑和1,2-二溴乙烷制得2,4,5-三溴-1-乙烯基咪唑，并通过Br→MgBr等交换反应以2→5→4的顺序选择性取代其Br原子反应。用臭氧或高锰酸钾可有效地从所得的多官能化咪唑中除去乙烯基。此方法的扩展允许首次合成噻吩并[2,3- d ]⇌[3,2- d ]-咪唑。
• Fast Halogenation of Some N<i>-</i>Heterocycles by Means of<i>N</i>,<i>N′</i>-Dihalo-5,5-dimethylhydantoin
  作者：Alexander H. Sandtorv、Hans-René Bjørsvik

  DOI：10.1002/adsc.201200723

  日期：2013.1.9

  selective and high-yielding halogenation process is reported. The method operates with imidazoles, pyrazoles, and indoles under benign reaction conditions. The developed process involves the use of N,N′-dihalo-5,5-dimethylhydantoins (halo=chlorine, bromine, iodine) as halogenation reagents that are activated by catalytic quantities of a strong Brønsted acid. Moreover, the halogenation process is switchable

  报道了瞬时的，选择性的和高产率的卤化方法。该方法在良性反应条件下使用咪唑，吡唑和吲哚进行操作。开发的方法涉及使用N，N'-二卤代5,5-二甲基乙内酰脲（卤代=氯，溴，碘）作为卤化试剂，该卤化试剂通过催化量的强布朗斯台德酸活化。而且，卤化过程是可切换的，以生产单或双卤代产物。研究与反应机理有关的问题，并公开了关于反应机理的建议。