4,5-二溴-1,2-二甲基-1H-咪唑 | 16954-05-5

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4,5-二溴-1,2-二甲基-1H-咪唑
• 英文名称: 4,5-dibromo-2-methyl-1-methylimidazole
• 英文别名: 4,5-dibromo-1,2-dimethyl-1H-imidazole；4,5-dibromo-1,2-dimethylimidazole；4,5-dibromo-1,2-dimethyl-1H-imidazole；4,5-dibromo-1,2-dimethyl-imidazole；1,2-Dimethyl-4,5-dibromoimidazole
• CAS: 16954-05-5
• 化学式: C₅H₆Br₂N₂
• 分子量: 253.924
• InChiKey: IRPMMLNFWNJAMH-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78°C
• 沸点：
  331.3±22.0 °C(Predicted)
• 密度：
  2.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4,5-Dibromo-1,2-dimethyl-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-1,2-dimethyl-1H-imidazole
CAS number: 16954-05-5

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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: C5H6Br2N2
Molecular weight: 253.9

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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-1,2-二甲基-1H-咪唑 在 正丁基锂 、 RuCl₂[(R)-(DM-BINAP)][(R)-DAIPEN] 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 异丙醇 为溶剂， 反应 18.08h， 生成 (S)-1-(4-bromo-1,2-dimethyl-1H-imidazol-5-yl)hexan-1-ol
  参考文献：
  名称：

  含咪唑和恶唑的合成脂质体A 4模拟物（sLXms）的不对称合成和生物学评估

  摘要：

  脂蛋白（LX）是内源性类花生酸，具有有效的生物作用，与炎症减轻一致。LXs昂贵的合成和代谢不稳定性可能会限制其治疗潜力。在这里，我们报告合成和表征新型咪唑/含恶唑的合成LX模拟物（sLXms）。假定的sLXms不对称合成的关键步骤包括Suzuki反应和不对称酮还原。使用稳定表达核因子Kappa B（NF kB）通过研究下游细胞因子的分泌来报道基因。咪唑的潜在相互作用/与LXS的分子靶恶唑，即G蛋白偶联受体（GPCR）甲酰肽受体2（ALX / FPR2）使用其中ALX / FPR2耦合到Gα一个电池系统研究q亚单位和受体相互作用是通过细胞内钙的动员来确定的。使用小鼠酵母聚糖诱导的腹膜炎模型评估了体内抗炎作用。总体而言，结构-活性关系（SAR）研究表明6C-二甲基咪唑（1R）-11的（R）受体在所测试的十种化合物中，它是最有效，最有效的消炎药。该分子在体内显着减弱了LPS诱导的NFkB活性，减

  DOI：

  10.1016/j.ejmech.2018.10.049
• 作为产物：
  描述：

  1,2-二甲基咪唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 以81%的产率得到4,5-二溴-1,2-二甲基-1H-咪唑
  参考文献：
  名称：

  含咪唑和恶唑的合成脂质体A 4模拟物（sLXms）的不对称合成和生物学评估

  摘要：

  脂蛋白（LX）是内源性类花生酸，具有有效的生物作用，与炎症减轻一致。LXs昂贵的合成和代谢不稳定性可能会限制其治疗潜力。在这里，我们报告合成和表征新型咪唑/含恶唑的合成LX模拟物（sLXms）。假定的sLXms不对称合成的关键步骤包括Suzuki反应和不对称酮还原。使用稳定表达核因子Kappa B（NF kB）通过研究下游细胞因子的分泌来报道基因。咪唑的潜在相互作用/与LXS的分子靶恶唑，即G蛋白偶联受体（GPCR）甲酰肽受体2（ALX / FPR2）使用其中ALX / FPR2耦合到Gα一个电池系统研究q亚单位和受体相互作用是通过细胞内钙的动员来确定的。使用小鼠酵母聚糖诱导的腹膜炎模型评估了体内抗炎作用。总体而言，结构-活性关系（SAR）研究表明6C-二甲基咪唑（1R）-11的（R）受体在所测试的十种化合物中，它是最有效，最有效的消炎药。该分子在体内显着减弱了LPS诱导的NFkB活性，减

  DOI：

  10.1016/j.ejmech.2018.10.049

文献信息

• Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus
  作者：Mebarek Bahnous、Abdelmalek Bouraiou、Meryem Chelghoum、Sofiane Bouacida、Thierry Roisnel、Farida Smati、Chafia Bentchouala、Philippe C. Gros、Ali Belfaitah

  DOI：10.1016/j.bmcl.2013.01.004

  日期：2013.3

  Several new highly functionalized imidazolium derivatives were synthesized, via appropriate synthetic routes, using imidazole, 1-methylimidazole and 2-phenyl-1-methylimidazole as key intermediates. The antibacterial activity of the prepared compounds was evaluated against: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella thipymurium using disk-diffusion and MIC methods

  通过咪唑，1-甲基咪唑和2-苯基-1-甲基咪唑为关键中间体，通过适当的合成途径，合成了几种新的高度官能化的咪唑鎓衍生物。用圆盘扩散法和MIC法评价了所制备化合物对大肠杆菌，金黄色葡萄球菌，铜绿假单胞菌和沙门氏菌的抗菌活性。报告了六种化合物的晶体X射线结构。
• Convenient multi-gram scale synthesis of polybrominated imidazoles building blocks
  作者：Mebarek Bahnous、Chabane Mouats、Yves Fort、Philippe C. Gros

  DOI：10.1016/j.tetlet.2006.01.066

  日期：2006.3

  The multi-gram scale polybromination of variously substituted imidazoles has been realized using a stoichiometric amount of the Br2–DMF complex. Good yields have been obtained compared to other methods using large amounts of acetic acid–sodium acetate buffer.

  使用化学计量的Br 2 -DMF配合物已经实现了多种克取代的咪唑的多克级多溴化反应。与使用大量乙酸-乙酸钠缓冲液的其他方法相比，已获得了良好的收率。
• Imidazole-Fused Enediynes by Selective C5–C4 Alkynylations of 4,5-Dibromoimidazoles
  作者：Fabio Bellina、Marco Lessi、Alessandro Panattoni、Luca Guglielmero、Pierpaolo Minei

  DOI：10.1055/s-0037-1610666

  日期：2019.2

  An efficient synthesis of symmetrical 1,2-disubstituted 4,5-dialkynylimidazoles by Sonogashira alkynylation of the corresponding 4,5-dibromo derivatives was developed. Moreover, through a careful tuning of the palladium ligand, unsymmetrical 1,2-disusbtituted 4,5-dialkynylimidazoles were also prepared through a regioselective C5 alkynylation of 4,5-dibromoimidazoles, followed by a second alkynylation involving the 4-bromo derivatives so obtained. This interesting class of imidazole-fused enediynes is also able to give thermal Bergman cycloaromatization (BC), as proved by DSC experiments.

  通过Sonogashira炔基化反应，可以高效合成对称的1,2-二取代的4,5-二炔基咪唑。此外，通过精心调节钯配体，还可以通过对4,5-二溴代衍生物进行选择性C5炔基化反应制备非对称的1,2-二取代的4,5-二炔基咪唑，随后进行第二次炔基化反应，涉及所得的4-溴代衍生物。这一有趣的咪唑-融合烯二炔类化合物还能够通过DSC实验证明具有热Bergman环芳化反应（BC）的能力。
• Development of an Efficient Process Towards the Benzimidazole BYK308944: A Key Intermediate in the Synthesis of a Potassium-Competitive Acid Blocker
  作者：Matthias Webel、Andreas Marc Palmer、Christian Scheufler、Dieter Haag、Bernd Müller

  DOI：10.1021/op9002505

  日期：2010.1.15

  important benzimidazole building block BYK308944 was elaborated using the Stobbe reaction as central element. BYK308944 constitutes an important intermediate for the preparation of 3,6,7,8-tetrahydrochromeno[7,8-d]imidazoles as potassium-competitive acid blockers. The new route relies on the hydroxymethylation of 1,2-dimethylimidazole as cheap starting material followed by oxidation of the corresponding alcohol

  重要的苯并咪唑结构单元BYK308944的全新合成工艺以Stobbe反应为中心元素。BYK308944构成了一种重要的中间体，用于制备3,6,7,8-四氢色酚[7,8- d ]咪唑类化合物，作为钾竞争性酸阻滞剂。新途径依赖于1,2-二甲基咪唑作为廉价的原料进行羟甲基化，然后氧化相应的醇，然后将所得醛与琥珀酸二乙酯进行Stobbe缩合反应。此新方法的所有合成步骤均经过优化，目的是建立适合大规模制备的工艺。
• Synthesis and Biological Evaluation of Bicyclo[1.1.1]pentane-Containing Aromatic Lipoxin A₄ Analogues
  作者：Benjamin Owen、Monica de Gaetano、Andrew Gaffney、Catherine Godson、Patrick J. Guiry

  DOI：10.1021/acs.orglett.2c02345

  日期：2022.8.19

  Bicyclo[1.1.1]pentanes (BCPs) are potential isosteric replacements for arenes and/or alkyl groups within drug candidates. We carried out an asymmetric synthesis of four BCP-containing synthetic lipoxin A4 mimetics (BCP-sLXms) in which the key steps were a Suzuki coupling, an asymmetric ketone reduction, and a triethylborane-initiated radical bicyclopentylation. These mimetics were screened for their impact

  脂氧素是炎症消退的重要驱动因素，表明潜在的治疗益处。双环[1.1.1]戊烷 (BCP) 是候选药物中芳烃和/或烷基的潜在等排替代品。我们对四种含有 BCP 的合成脂氧素 A 4模拟物 (BCP-sLXms)进行了不对称合成，其中关键步骤是 Suzuki 偶联、不对称酮还原和三乙基硼烷引发的自由基双环戊基化。筛选了这些模拟物对炎症反应的影响，发现一种咪唑-BCP-sLXm ( 6a ) 具有高抗炎活性。