4-碘-1-甲苯磺酰-1H-咪唑 | 163854-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-碘-1-甲苯磺酰-1H-咪唑
• 英文名称: N-tosyl-4-iodoimidazole
• 英文别名: 4-Iodo-1-tosyl-1H-imidazole；4-iodo-1-(4-methylphenyl)sulfonylimidazole
• CAS: 163854-63-5
• 化学式: C₁₀H₉IN₂O₂S
• mdl: MFCD04039580
• 分子量: 348.164
• InChiKey: GNMAMHYZZVUENR-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148°C
• 溶解度：
  溶于氯仿、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Iodo-1-tosyl-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-Iodo-1-tosyl-1H-imidazole
CAS number: 163854-63-5

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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: C10H9IN2O2S
Molecular weight: 348.2

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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, sulfur oxides.

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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-碘-1-甲苯磺酰-1H-咪唑 在 manganese(IV) oxide 、 四(三苯基膦)钯 、 2,9-二甲基-4,7二苯基-1,10-菲啰啉 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.0h， 生成 (E)-4-(3-methoxystyryl)-1-tosyl-1H-imidazole
  参考文献：
  名称：

  通过量身定制和优化的氧化Heck交叉偶联功能实现咪唑骨架的功能化

  摘要：

  公开了芳族硼酸与乙烯基咪唑的一般和选择性Pd催化交叉偶联。与大多数交叉偶联反应不同，该方法在没有碱的情况下运行良好，避免了副产物的形成。氮基配体（特别是红霉素）的存在可大大提高反应性。该方法涉及MnO 2作为氧化Pd（0）→Pd（II）的氧化剂，它比以前文献中报道的要弱得多。这允许使用具有多个官能团的反应物。范围和限度研究涉及一系列24种硼酸，其中18种提供的TM产率在41–95％范围内。所公开的方法构成了在咪唑支架上进行氧化性Heck交叉偶联的第一种通用方法，该方法还可以与其他杂环一起选择。

  DOI：

  10.1002/adsc.202000909
• 作为产物：
  描述：

  对甲苯磺酰氯 、 4-碘-1(H)-咪唑 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以68%的产率得到4-碘-1-甲苯磺酰-1H-咪唑
  参考文献：
  名称：

  咪唑骨架上 Sonogashira 偶联反应的范围和机械限制

  摘要：

  开发并研究了将末端炔烃连接到咪唑主链的 Sonogashira 偶联反应方法。该方法表现出良好的官能团耐受性，并以 70-93% 的产率提供目标 4-炔基化咪唑。炔试剂通过 DFT 计算表征，由此产生静电势面 (EPS)。揭示了三键的 EPS 与偶联反应的成功之间的明确相关性。如果 EPS 在 –94 到 –105 kJ mol–1 的范围内，则耦合成功。通过辅助基团（叔丁基二甲基甲硅烷基）使一类不成功的试剂（炔醇）相容。这些修饰试剂的 EPS 与模型的 EPS 相似，这些辅助辅助试剂随后以优异的产率成功耦合。

  DOI：

  10.1002/ejoc.201500520

文献信息

• Palladium catalysed coupling of imidazoles to alkynyl and vinyl substrates
  作者：Matthew D Cliff、Stephen G Pyne

  DOI：10.1016/0040-4020(96)00823-x

  日期：1996.10

  Methods for preparing 4-substituted imidazoles from the palladium(0) catalysed couplings of N-protected 4-haloimidazoles with alkynes or alkynyl- and vinyltrialkyltin derivatives or from the coupling reactions of 4-trimethylstannylimidazole 9 with aryl and vinyliodides and bromides under Stille conditions is reported.

  由N-保护的4-卤代咪唑与炔烃或炔基和乙烯基三烷基锡衍生物的钯（0）催化偶合或在Stille条件下由4-三甲基苯乙烯基咪唑9与芳基和乙烯基碘化物及溴化物的偶合反应制备4-取代的咪唑的方法是报告。
• HETEROARYL-PYRAZOLE DERIVATIVE
  申请人：Nakamura Toshio

  公开号：US20130137865A1

  公开（公告）日：2013-05-30

  A compound represented by formula [I] and a pharmaceutically accepted salt of said compound are a novel compound and a pharmaceutically accepted salt thereof which exert antagonistic activity against group II metabotropic glutamate (mGlu) receptors, and are effective as a novel preventive or therapeutic agent for disorders such as mood disorders (depressive disorder, bipolar disorder, etc.), anxiety disorders (generalized anxiety disorder, panic disorder, obsessive-compulsive disorder, social anxiety disorder, posttraumatic stress disorder, a specific phobic disorder, acute stress disorder, etc.), schizophrenia, Alzheimer's disease, cognitive impairment, dementia, drug dependence, convulsions, shivering, pain, sleep disorders, and the like.

  公式[I]所代表的化合物及其药学上可接受的盐是一种新颖的化合物及其药学上可接受的盐，对II类代谢型谷氨酸（mGlu）受体具有拮抗活性，并且作为一种新型预防或治疗剂对情绪障碍（抑郁症、双相情感障碍等）、焦虑障碍（广泛性焦虑障碍、恐慌障碍、强迫症、社交焦虑障碍、创伤后应激障碍、特定恐惧障碍、急性应激障碍等）、精神分裂症、阿尔茨海默病、认知障碍、痴呆、药物依赖、抽搐、颤抖、疼痛、睡眠障碍等疾病具有有效性。
• Preparation and Diels−Alder Chemistry of 4-Vinylimidazoles
  作者：Carl J. Lovely、Hongwang Du、Rasapalli Sivappa、Manojkumar R. Bhandari、Yong He、H. V. Rasika Dias

  DOI：10.1021/jo0626008

  日期：2007.5.1

  circumvented to a large extent by the choice of reaction conditions. Limited reactions were observed with other dienophiles, providing the expected cycloadducts in most cases, although an abnormal adduct was obtained in one case with dimethyl acetylene dicarboxylate. These substrates also participate in regioselective Diels−Alder reactions with monoactivated dienophiles, but require fairly forcing conditions

  从相应的4-碘咪唑或从尿酸制备了各种4-乙烯基咪唑衍生物。报道了几种详细说明这些乙烯基咪唑及其Diels-Alder反应的方法。在本研究过程中制备的所有乙烯基咪唑均与N反应-苯基马来酰亚胺很容易被温和的热活化而形成单个环加合物，在大多数情况下是初始的非芳族加合物。对于更多的富电子底物，尽管可以通过选择反应条件在很大程度上避免这些初始环加合物发生芳构化，烯键反应和氧化的趋势。观察到与其他亲二烯体的反应有限，在大多数情况下可提供预期的环加合物，尽管在一种情况下，与乙炔二甲酸二甲酯反应可得到异常的加合物。这些底物还与单活化的亲二烯体参与区域选择性Diels-Alder反应，但需要相当强的条件，因此仅以适度的收率提供了芳构化的环加合物。对咪唑部分2-位的取代基作用进行了研究，在其中耐受给电子和弱吸电子的取代基。另外，已经研究了具有末端取代的乙烯基部分的几种底物。
• Convenient Synthesis of Furo[3,2-b]quinolin-4(1H)-ones
  作者：Veronika Králová、Miroslav Soural、Radim Horák、Pavel Hradil

  DOI：10.1055/s-0039-1691743

  日期：2020.6

  from readily available 4-ethynyl-[1,3]dioxolo[4,5-c]quinolone as the key starting material. After Sonogashira (hetero)arylation, formation of the furoquinoline scaffold was accomplished using methanesulfonic acid and metal-free conditions. Although the cyclization was affected by the substitution of reaction intermediates, the method allowed the preparation of derivatives varying at the C3-position.

  在这项工作中，我们报告了从现成的 4-乙炔基-[1,3] 二氧杂环 [4,5-c] 喹诺酮中简单合成呋喃 [3,2-b] 喹啉-4(1H)-酮作为关键起始材料。Sonogashira（杂）芳基化后，使用甲磺酸和无金属条件完成呋喃喹啉支架的形成。尽管环化受反应中间体取代的影响，但该方法允许制备 C3 位变化的衍生物。
• Stille Cross-Coupling for the Functionalization of the Imidazole Backbone: Revisit, Improvement, and Applications of the Method
  作者：Alexander H. Sandtorv、Karl Wilhelm Törnroos、Hans-René Bjørsvik

  DOI：10.1002/ejoc.201500328

  日期：2015.6

  We have revisited the Stille coupling reaction for the functionalization of the imidazole backbone. In this context CuI was exploited as a co-catalyst, which resulted in significantly improved yields of target coupling products. Furthermore, a systematic investigation of the effect of the auxiliary group on the N-1-ring atom was performed. When mono-coupling is desired, the Tosyl (Tos) group is superior

  我们重新审视了用于咪唑骨架功能化的 Stille 偶联反应。在这种情况下，CuI 被用作助催化剂，从而显着提高了目标偶联产物的产率。此外，还对辅助基团对 N-1 环原子的影响进行了系统研究。当需要单偶联时，甲苯磺酰基 (Tos) 基团优于（二甲氨基）磺酰基 (DMAS) 基团，以显着更高的产率提供相应的 4 偶联咪唑。然而，当首选双耦合时，DMAS 组对于耦合程序的成功是必不可少的。利用该反应协议，我们成功地展示了使用 N-DMAS-4,5-二碘咪唑作为底物的 Stille 双偶联的第一个例子。