4,5-二碘-1-甲基-1H-咪唑 | 37067-96-2

• 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 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 4,5-二碘-1-甲基-1H-咪唑
• 英文名称: 4,5-diiodo-1-methyl-1H-imidazole
• 英文别名: 1-methyl-4,5-diiodoimidazole；4,5-diiodo-1-methylimidazole
• CAS: 37067-96-2
• 化学式: C₄H₄I₂N₂
• mdl: MFCD03001336
• 分子量: 333.898
• InChiKey: LFQKCAODRSVYMI-UHFFFAOYSA-N

物化性质

• 熔点：
  142-143°C
• 沸点：
  382.2±27.0 °C(Predicted)
• 密度：
  2.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 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：
  存储条件：2-8°C，避光干燥密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4,5-Diiodo-1-methyl-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-1-methyl-1H-imidazole
CAS number: 37067-96-2

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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: C4H4I2N2
Molecular weight: 333.9

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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

反应信息

• 作为反应物：
  描述：

  4,5-二碘-1-甲基-1H-咪唑 生成 5-碘-1-甲基咪唑
  参考文献：
  名称：

  SHVARTSBERG M. S.; BIZHAN L. N.; SINYAKOV A. N.; MYASNIKOVA R. N., IZV. AN CCCP CEP. XIM., 1979, HO 7, 1563-1569

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基咪唑 在 1-butyl-3-methylpyridinium dichloroiodate 作用下， 反应 5.0h， 以69%的产率得到4,5-二碘-1-甲基-1H-咪唑
  参考文献：
  名称：

  [EN] NOVEL RECYCLABLE IODINATING AGENT AND ITS APPLICATIONS
  [FR] NOUVEL AGENT D'IODATION RECYCLABLE ET SES APPLICATIONS

  摘要：

  本发明提供了一种新颖的可回收催化剂，其化学式为A，[在此处应插入公式A] 其中X选自以下组中的[在此处应插入公式]。本发明还提供了一种新颖的可回收碘化剂，其化学式为I、II或III，以及其合成过程。[在此处应插入公式I、II和III]此外，本发明提供了一种通过使用化学式为(I)的可回收催化剂对胺和杂环化合物进行卤化的过程。

  公开号：

  WO2016113757A1

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。
• Photoinduced Bergman cycloaromatization of imidazole-fused enediynes
  作者：Zhengrong Zhao、Justin G. Peacock、Daniel A. Gubler、Matt A. Peterson

  DOI：10.1016/j.tetlet.2004.12.136

  日期：2005.2

  imidazole-fused’ enediynes—were synthesized and their reactivities in photoinduced Bergman cycloaromatization reactions were determined. The more conformationally rigid analogues gave cycloaromatized products in good yields upon irradiation (450 W low-pressure mercury lamp, ambient temperature). A bicyclic analogue (3) was shown to cleave supercoiled plasmid DNA.

  合成了一系列的4,5-双-（炔-1-基）咪唑（“咪唑稠合”的二炔），并确定了它们在光诱导的Bergman环芳烃化反应中的反应性。构象更严格的类似物在辐射下（450 W低压汞灯，环境温度）以良好的收率提供了环芳烃化的产品。显示双环类似物（3）切割超螺旋质粒DNA。
• [EN] CONDENSED PYRIDINES AND PYRIMIDINES WITH TIE2 (TEK) ACTIVITY<br/>[FR] PYRIDINES CONDENSEES ET PYRIMIDINES A ACTIVITE TIE2 (TEK)
  申请人：ASTRAZENECA AB

  公开号：WO2004013141A1

  公开（公告）日：2004-02-12

  A compound of the Formula (I), wherein A together with the carbon atoms to which it is attached forms a fused 5-membered heteroaryl ring, wherein said heteroaryl ring contains 1 or 2 heteroatoms selected from O, N and S, and wherein the 5-membered ring containing G is linked to the ring formed by A in the meta position to the bridgehead carbon marked # in Formula (I); G is selected from O, S and NR5; Z is selected from N and CR6; Q1 is selected from optionally substituted aryl and heteroaryl, and the substituents R1 to R6 are as defined in the text for use in the production of an anti-angiogenic effect in a warm blooded animal such as man.

  化合物的公式（I），其中A与其连接的碳原子一起形成一个融合的5-成员杂环芳烃环，其中所述的杂环芳烃环包含1个或2个从O、N和S中选择的杂原子，并且包含G的5-成员环与在公式（I）中标记为桥头碳#的A形成的环在间位连接；G从O、S和NR5中选择；Z从N和CR6中选择；Q1从可选择的取代芳基和杂环芳基中选择，取代基R1到R6如文本中所定义，用于在温血动物（如人）中产生抗血管生成作用。
• Ruthenium piano-stool complexes bearing imidazole-based PN ligands
  作者：Peter C. Kunz、Indre Thiel、Anna Louisa Noffke、Guido J. Reiß、Fabian Mohr、Bernhard Spingler

  DOI：10.1016/j.jorganchem.2011.10.006

  日期：2012.1

  cyclopentadienyl ruthenium(II) with imidazole-based PN ligands have been synthesized starting from the precursor complexes [CpRu(C10H8)]PF6, [CpRu(NCMe)3]PF6 and [CpRu(PPh3)2Cl]. PN ligands used are imidazol-2-yl, -4-yl and -5-yl phosphines. Depending on the ligand and precursor different types of coordination modes were observed; in the case of polyimidazolyl PN ligands these were κ1P-monodentate, κ2P,N-, κ2N,N-

  从前体复合物[CpRu（C 10 H 8）] PF 6，[CpRu（NCMe）3 ] PF 6和[ CpRu（PPh 3）2 Cl]。所用的PN配体是咪唑-2-基，-4-基和-5-基膦。 取决于配体和前体，观察到不同类型的配位模式。在polyimidazolyl PN的情况下配体这些都是κ 1个P -monodentate，κ 2 P，N - ，κ 2 N，N- -和κ 3 N，N，N- -螯合剂和μ-κ P：κ 2 N，N-桥接。的固态结构[CPRU（1A）2 CL]·H 2 O（5 。 ħ 2 O）和[CPRU（μ-κ 2 -N，N- κ ' 1 -P -图2b）} 2 ] （C 6H 5 PO 3 H）2（C 6 H 5 PO 3 H 2）2也是确定的[CpRu（2b）} 2 ]（PF 6）2的水解产物。2CH 3 CN（7b中。 2CH 3 CN）进行了测定（1A  =咪唑-2-
• Total Synthesis of the Leucetta-Derived Alkaloid Calcaridine A
  作者：H. Dias、Carl Lovely、Panduka Koswatta、Rasapalli Sivappa

  DOI：10.1055/s-0029-1216929

  日期：2009.9

  A biomimetically guided total synthesis of the Leucetta-derived aminoimidazole alkaloid, calcaridine A, is described. The synthesis relies on position selective metalations of a 4,5-diiodo­imidazole derivative to provide a tetrasubstituted imidazole. Subjection of this polysubstituted imidazole derivative to oxidative rearrangement with a Davis oxaziridine provides the corresponding imidazolone core of calcaridine A.

  描述了一种仿生指导的全合成方法，用于合成源自Leucetta的氨基咪唑生物碱卡尔卡里丁A。该合成依赖于对4,5-二碘咪唑衍生物的选择性金属化，以提供四取代的咪唑。将这种多取代的咪唑衍生物进行氧化重排，使用Davis氧杂喹啉，得到卡尔卡里丁A的相应咪唑酮核心。