4,5-二碘-2-甲基咪唑 | 73746-44-8

• 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: 4,5-二碘-2-甲基咪唑
• 英文名称: 4,5-diiodo-2-methyl-1H-imidazole
• 英文别名: 4,5-diiodo-2-methyl-imidazole；4,5-diiodo-2-methyl imidazole；4,5-diiodo-2-methylimidazole；2-methyl-4,5-diidoimidazole；4,5-diiodo-2-methyl-1H-imidazole；4,5-Dijod-2-methyl-1H-imidazol
• CAS: 73746-44-8
• 化学式: C₄H₄I₂N₂
• mdl: MFCD00464337
• 分子量: 333.898
• InChiKey: WFEZOLYJPCODOA-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195°C
• 沸点：
  434.9±30.0 °C(Predicted)
• 密度：
  2.750±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S37/39
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2933290090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H319

SDS

Name:	4 5-Diiodo-2-methyl-1h-imidazole 97% Material Safety Data Sheet
Synonym:
CAS:	73746-44-8

Section 1 - Chemical Product MSDS Name:4 5-Diiodo-2-methyl-1h-imidazole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
73746-44-8	4,5-Diiodo-2-methyl-1H-imidazole	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 73746-44-8: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: beige
Odor: odorless - slight odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 194 - 195 deg C(decom)
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C4H4I2N2
Molecular Weight: 333.89

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen iodide, iodine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 73746-44-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4,5-Diiodo-2-methyl-1H-imidazole - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 73746-44-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 73746-44-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 73746-44-8 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

4,5-二碘-2-甲基咪唑是一种有机中间体，能够表现出铁电性和压电性，并倾向于产生天然扭曲或弹性的晶体结构。其独特的分子结构赋予了该化合物显著的电子和机械特性，适用于多种应用领域，例如数据存储、能量存储、或者作为压电启动器、传感器或换能器。

制备方法

将18.5克碘（73.1毫摩尔）溶解在90毫升氯仿中，然后缓慢加入到含有2-甲基咪唑（3.0克，36.5毫摩尔）的90毫升2M NaOH溶液中。混合物开始混浊，但在2.5小时后变为澄清的两相体系。分离各层，并向有机层中加入10.5毫升乙酸（183毫摩尔），以中和反应并调整pH值至约5-6。随后会析出固体，将其过滤并从温暖的乙腈中重结晶，最终得到8.5克4,5-二碘-2-甲基咪唑，产率为69%。

反应信息

• 作为反应物：
  描述：

  4,5-二碘-2-甲基咪唑 在 正丁基锂 、 水 作用下， 生成 4-碘-2-甲基-1H-咪唑
  参考文献：
  名称：

  具有心脏刺激活性的2（1H）-喹啉酮。3.6-咪唑-1-基衍生物的合成和生物学性质。

  摘要：

  合成了一系列的6-咪唑-1-基-8-甲基-2（1H）-喹啉酮并评估了狗的心脏刺激活性。大多数化合物是由适当的6-咪唑-1-基-2（1H）-喹啉酮前体或通过硫酸催化的N-（4-杂芳基苯基）-3-乙氧基丙烯酰胺的环化反应制备的。在6-（2,4-二甲基咪唑-1-基）-8-甲基-2（1H）-喹啉酮（1）中引入一系列5-取代基可降低麻醉犬的正性肌力（dP / dtmax百分比增加）尽管2-碘被碘（10）或氰基（11）取代基取代的耐受性很好。2-甲基-4-氯（15）和2-甲基-4-（甲硫基）（22）衍生物显示出与1相似的效价（dP / dtmax增加40-50％，10-12.5微克/ kg），并且这些化合物的效力是米力农的3-5倍。碘的介绍（14），氰基（16）或乙酰基（17）取代基变成4位，正离子活性减半。在清醒的狗中，11（0.25 mg / kg）和16和17（0.125 mg / kg）的心脏收缩力（QA间隔降低）增加到1（0

  DOI：

  10.1021/jm00127a025
• 作为产物：
  描述：

  2-甲基咪唑 在 一氯化碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以55%的产率得到4,5-二碘-2-甲基咪唑
  参考文献：
  名称：

  具有心脏刺激活性的2（1H）-喹啉酮。3.6-咪唑-1-基衍生物的合成和生物学性质。

  摘要：

  合成了一系列的6-咪唑-1-基-8-甲基-2（1H）-喹啉酮并评估了狗的心脏刺激活性。大多数化合物是由适当的6-咪唑-1-基-2（1H）-喹啉酮前体或通过硫酸催化的N-（4-杂芳基苯基）-3-乙氧基丙烯酰胺的环化反应制备的。在6-（2,4-二甲基咪唑-1-基）-8-甲基-2（1H）-喹啉酮（1）中引入一系列5-取代基可降低麻醉犬的正性肌力（dP / dtmax百分比增加）尽管2-碘被碘（10）或氰基（11）取代基取代的耐受性很好。2-甲基-4-氯（15）和2-甲基-4-（甲硫基）（22）衍生物显示出与1相似的效价（dP / dtmax增加40-50％，10-12.5微克/ kg），并且这些化合物的效力是米力农的3-5倍。碘的介绍（14），氰基（16）或乙酰基（17）取代基变成4位，正离子活性减半。在清醒的狗中，11（0.25 mg / kg）和16和17（0.125 mg / kg）的心脏收缩力（QA间隔降低）增加到1（0

  DOI：

  10.1021/jm00127a025

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。
• Substituted inmidazoles as bombesin receptor subtype-3 modulators
  申请人：Chen David

  公开号：US20100022598A1

  公开（公告）日：2010-01-28

  Certain novel substituted imidazoles are ligands of the human bombesin receptor and, in particular, are selective ligands of the human bombesin receptor subtype-3 (BRS-3). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of BRS-3, such as obesity, and diabetes.

  某些新型取代咪唑是人类炸弹素受体的配体，特别是人类炸弹素受体亚型-3（BRS-3）的选择性配体。因此，它们对于治疗、控制或预防对BRS-3调节敏感的疾病和紊乱，如肥胖症和糖尿病，具有用处。
• Synthesis, structure–activity relationship studies, and identification of novel 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine derivatives as dual orexin receptor antagonists. Part 1
  作者：Thierry Sifferlen、Ralf Koberstein、Emmanuelle Cottreel、Amandine Boller、Thomas Weller、John Gatfield、Catherine Brisbare-Roch、Francois Jenck、Christoph Boss

  DOI：10.1016/j.bmcl.2013.01.088

  日期：2013.4

  A novel series of non-peptidic OX1R/OX2R orexin receptor antagonists was prepared by heterocyclic replacement of the dimethoxyphenyl moiety contained in the tetrahydroisoquinoline core skeleton of almorexant. Introduction of substituted imidazole moieties delivered potent dual orexin receptor antagonists with nanomolar potency for hOX1R and hOX2R suitable for further fine-tuning. The preparation of

  通过杂环取代almorexant的四氢异喹啉核心骨架中的二甲氧基苯基部分，制备了一系列新的非肽类OX 1 R / OX 2 R食欲素受体拮抗剂。引入取代的咪唑基团可提供有效的双orexin受体拮抗剂，对hOX 1 R和hOX 2 R具有纳摩尔浓度，适用于进一步的微调。这些通讯中描述了这些新的orexin受体拮抗剂的制备以及初步的结构-活性关系研究的结果。
• A simple method for iodination of heterocyclic compounds using HIO4/NaCl/silica gel/H2SO4 in water
  作者：Abolfazl Hosseini、Mohammad A. Khalilzadeh、Masoumeh Hosseinzadeh、Mahmoud Tajbakhsh

  DOI：10.1007/s00706-011-0611-6

  日期：2012.4

  AbstractA fast and simple method for iodination of some heterocycles is reported. The reactions were carried out in water, using HIO4/H2SO4/NaCl/silica gel at moderate temperatures of 25–50 °C. Graphical Abstract

  摘要报道了一种快速简单的碘化某些杂环的方法。反应在25–50°C的中等温度下使用HIO 4 / H 2 SO 4 / NaCl /硅胶在水中进行。 图形概要
• Aromatic iodination in aqueous solution. A new lease of life for aqueous potassium dichloroiodate
  作者：Simon J Garden、José C Torres、Simone C de Souza Melo、Alexandre S Lima、Angelo C Pinto、Edson L.S Lima

  DOI：10.1016/s0040-4039(01)00105-8

  日期：2001.3

  A re-investigation of the use of aqueous potassium dichloroiodate (KICl2) as an iodinating agent for aromatic compounds has found the reagent to be more generally applicable than previously known. The reagent has been found to give excellent yields of iodinated heterocyclic compounds, such as isatin, imidazole and pyrazole.

  重新研究使用二氯碘酸钾水溶液（KICl 2）作为芳族化合物的碘化剂，发现该试剂比以前已知的更通用。已发现该试剂可提供优异产率的碘化杂环化合物，如Isatin，咪唑和吡唑。