4,5-二碘咪唑 | 15813-09-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 4,5-二碘咪唑
• 中文别名: 4,5-1-(H)-二碘咪唑；4,5-二碘-1H-咪唑
• 英文名称: 4,5-diiodo-1H-imidazole
• 英文别名: 4,5-diiodoimidazole
• CAS: 15813-09-9
• 化学式: C₃H₂I₂N₂
• mdl: MFCD00963878
• 分子量: 319.871
• InChiKey: XMWPTVMTXKJONE-UHFFFAOYSA-N

物化性质

• 熔点：
  197-198°C
• 沸点：
  436.9±30.0 °C(Predicted)
• 密度：
  3.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933290090
• 危险类别：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境中保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4,5-Diiodo-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-Diiodo-1H-imidazole
CAS number: 15813-09-9

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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, refrigerated.
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: C3H2I2N2
Molecular weight: 319.9

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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 Iodide.

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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

制备方法与用途

应用：4,5-二碘-1H-咪唑是一种杂环衍生物，可用作医药中间体。

反应信息

• 作为反应物：
  描述：

  4,5-二碘咪唑 在 Oxone 作用下， 以 水 为溶剂， 以64.3%的产率得到4,5-diiodylimidazole
  参考文献：
  名称：

  低爆炸压力的富含碘的致密化合物作为杀菌剂

  摘要：

  制备了十五种碘化合物和六种碘化合物，其碘含量在45.3％至89.0％之间。通过使用Oxone，从相应的碘代化合物获得单，二和三碘基化合物。所有化合物均通过IR，1 H和13 C NMR，元素分析和差示扫描量热法（DSC）表征。冲击敏感度通过使用BAM（BundesamtfürMaterialforschung）方法进行测量。根据计算出的地层热和实验密度，采用Cheetah 6.0预测了爆轰性能和爆轰产物。含碘物质的总百分比（wt％）（I 2，HI和气相中的I）范围为46.7（21）至88.94％（11）被发现在爆炸产物中。碘和/或含碘物种的高浓度和易获取性对于开发适合用作特工击败武器（ADW）的材料非常重要。

  DOI：

  10.1002/chem.201300565
• 作为产物：
  描述：

  咪唑 在 sodium hydroxide 、 碘 、 potassium iodide 作用下， 以 水 为溶剂， 以90%的产率得到4,5-二碘咪唑
  参考文献：
  名称：

  通过碘-铜交换反应对咪唑进行选择性官能化。

  摘要：

  受保护的4,5-二碘咪唑与（PhMe2CCH2）2CuLi的区域选择性反应可生成5-杯化的咪唑，该咪唑易于与各种亲电试剂反应，以高收率提供官能化的咪唑；值得注意的是，这些所得的单碘咪唑在诸如醛或酮的敏感官能团的存在下再次进行碘-铜交换反应。

  DOI：

  10.1039/b603419e

文献信息

• Metal-mediated base pairing in DNA involving the artificial nucleobase imidazole-4-carboxylate
  作者：Nikolas Sandmann、Denise Defayay、Alexander Hepp、Jens Müller

  DOI：10.1016/j.jinorgbio.2018.10.013

  日期：2019.2

  Cu(II)-mediated base pairing. Moreover, it is the smallest nucleoside known to form stable Cu(II)-mediated base pairs. Structures of the X-Cu(II)-X and X-Ag(I)-X base pairs are proposed, too, based on molecular structures obtained using the model nucleobase 1-benzyl-1H-imidazole-4-carboxylate.

  据报道，在金属介导的碱基配对中，将咪唑-4-羧酸盐（X）用作人工核碱基。为此，合成了相应的脱氧核糖核苷，并在结构上表征为其钠盐（1,2-二脱氧-1-（4-羧基咪唑-1-基）-d-呋喃核糖钠。将脱氧核糖核苷掺入不同的DNA双链体（平行链和反平行链）中，并研究了它们的Cu（II）-和Ag（I）结合行为。结果表明，可以同时形成X-Cu（II）-X和X-Ag（I）-X碱基对，前者比后者更稳定。X-Cu（II）-X碱基对的形成伴随着反平行链双链体双链解链温度升高约20°C，平行链双链体的双链体解链温度升高约12°C。咪唑-4-羧酸盐代表Cu（II）介导的碱基配对的第一个基于咪唑的核苷。而且，它是已知形成稳定的Cu（II）介导的碱基对的最小核苷。基于使用模型核碱基1-苄基-1H-咪唑-4-羧酸盐获得的分子结构，也提出了X-Cu（II）-X和X-Ag（I）-X碱基对的结构。
• [EN] AZOLIUM AND PURINIUM SALT ANTICANCER AND ANTIMICROBIAL AGENTS<br/>[FR] ANTIMICROBIENS ET ANTINÉOPLASIQUES DE SELS D'AZOLIUM ET DE PURINIUM
  申请人：UNIV AKRON

  公开号：WO2012149523A1

  公开（公告）日：2012-11-01

  Singly and multiply charged imidazolium cations (ICs) have been identified as a class of chemical compositions that possess potent antineoplastic, antibacterial and antimicrobial properties. The imidazolium cations disclosed demonstrate greater or equivalent potency towards cancerous cells as the current clinical standard, cisplatin. These imidazolium cations, however, achieve this efficacy without any of the known toxic side effects caused by heavy metal-based antineoplastic drugs such as cisplatin.

  单电荷和多电荷咪唑阳离子（ICs）已被确认为一类具有强效抗肿瘤、抗菌和抗微生物特性的化学成分。所披露的咪唑阳离子对癌细胞表现出比当前临床标准顂铂更高或相等的效力。然而，这些咪唑阳离子在不引起类似顂铂等重金属抗肿瘤药物已知的毒副作用的情况下实现了这种功效。
• [EN] N-ACYLPIPERIDINE ETHER TROPOMYOSIN-RELATED KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE APPARENTÉS À LA N-ACYLPIPÉRIDINE ÉTHER TROPOMYOSINE
  申请人：PFIZER LTD

  公开号：WO2015092610A1

  公开（公告）日：2015-06-25

  The present invention relates to compounds of Formula (I) described herein and their pharmaceutically acceptable salts, and their use in medicine, in particular as Trk antagonists.

  本发明涉及本文所述的式(I)化合物及其药学上可接受的盐，以及它们在医学上的用途，特别是作为Trk拮抗剂。
• Bergman cycloaromatization of imidazole-fused enediynes: the remarkable effect of N-aryl substitution
  作者：Zhengrong Zhao、Yunshan Peng、N.Kent Dalley、John F Cannon、Matt A Peterson

  DOI：10.1016/j.tetlet.2004.02.152

  日期：2004.4

  A series of N-aryl substituted `imidazole-fused' (Z) 3-ene-1,5-diynes was prepared and kinetic parameters for their Bergman cycloaromatization reactivities were determined. N-Arylation enhanced rates relative to N-alkyl derivatives by up to sevenfold (ANOVA p<0.0001). The greatest enhancement was exhibited by the N-phenyl derivative (sevenfold at 145 °C).

  制备了一系列的N-芳基取代的“咪唑稠合的”（Z）3-烯-1,5-二炔，并确定了其Bergman环芳化反应活性的动力学参数。N-芳基化相对于N-烷基衍生物的速率提高了七倍（ANOVA p <0.0001）。N-苯基衍生物表现出最大的增强作用（在145°C时为七倍）。
• IMIDAZOPIPERAZINE INHIBITORS OF TRANSCRIPTION ACTIVATING PROTEINS
  申请人：Board of Regents, The University of Texas System

  公开号：US20190298729A1

  公开（公告）日：2019-10-03

  The present disclosure relates to heterocyclic compounds and methods which may be useful as inhibitors of transcription activating proteins such as CBP and P300 for the treatment or prevention of diseases such as proliferative diseases, inflammatory disorders, autoimmune diseases, and fibrotic diseases.

  本公开涉及杂环化合物和方法，这些方法可能作为转录激活蛋白（如CBP和P300）的抑制剂，用于治疗或预防增殖性疾病、炎症性疾病、自身免疫疾病和纤维化疾病。