(1H-苯并咪唑-2-亚甲基)胺 | 5805-57-2

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (1H-苯并咪唑-2-亚甲基)胺
• 中文别名: (1H-苯并[d]咪唑-2-基)甲胺
• 英文名称: 2-Aminomethylbenzimidazole
• 英文别名: (1H-benzo[d]imidazol-2-yl)methanamine；1H-benzimidazol-2-ylmethanamine
• CAS: 5805-57-2
• 化学式: C₈H₉N₃
• mdl: MFCD00464052
• 分子量: 147.18
• InChiKey: UCOSRTUSVXHIMK-UHFFFAOYSA-N

物化性质

• 熔点：
  101.5 °C
• 沸点：
  384.3±25.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (1H-Benzo[d]imidazol-2-yl)methanamine
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: (1H-Benzo[d]imidazol-2-yl)methanamine
CAS number: 5805-57-2

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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.
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: C8H9N3
Molecular weight: 147.2

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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.

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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

简介

(1H-苯并咪唑-2-亚甲基)胺又称为2-氨甲基苯并咪唑。这种化合物是一种重要的精细化工原料。由于含苯并咪唑功能团的有机化合物具有较强的配位能力和多样的配位构型，因此含苯并咪唑配体的配位化学成为非常活跃的研究课题。

制备方法

将邻苯二胺（1.08g）、甘氨酸（1.12g）置于20mL高压釜中，并加入6mol/L的盐酸（14mL），搅拌均匀后，在120℃恒温箱中保温48小时。冷却至室温后，使用浓氨水调节pH值至约8，继续冷却至4℃以下，析出固体。抽滤后，产物用蒸馏水重结晶，并加入活性炭进行脱色处理，最终得到无色针状(1H-苯并咪唑-2-亚甲基)胺，产率为72%。

反应信息

• 作为反应物：
  描述：

  (1H-苯并咪唑-2-亚甲基)胺 在 potassium carbonate 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 10.0h， 生成 N-[(6,8-dibromo-4-oxoquinazolin-3-yl)methyl]-2-[2-[(1,3-dioxoisoindol-2-yl)methyl]benzimidazol-1-yl]acetamide
  参考文献：
  名称：

  Misra, Vinay S.; Shah, Pramilla; Saxena, V. K., Journal of the Indian Chemical Society, 1982, vol. 59, # 9, p. 1074 - 1076

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(aminomethyl)benzimidazole dihydrochloride 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (1H-苯并咪唑-2-亚甲基)胺
  参考文献：
  名称：

  BENZIMIDAZOLE COMPOUNDS THAT ARE VITRONECTIN RECEPTOR ANTAGONISTS

  摘要：

  公开号：

  EP1135374B9
• 作为试剂：
  描述：

  2-(2-(2-(叠氮乙氧基)乙氧基)乙氧基)乙醛 、 N-[2-(6-amino-1,3-dioxobenzo[de]isoquinolin-2-yl)ethyl]-2-hydrazinylacetamide 在 (1H-苯并咪唑-2-亚甲基)胺 作用下， 生成
  参考文献：
  名称：

  INJECTABLE AND STABLE HYDROGELS WITH DYNAMIC PROPERTIES MODULATED BY BIOCOMPATIBLE CATALYSTS

  摘要：

  一种水凝胶组合物包括：（1）聚合物网络，包括第一水溶性聚合物和第二水溶性聚合物，通过动态键交联；和（2）催化剂，用于调节聚合物网络的交联交换速率。

  公开号：

  US20180104348A1

文献信息

• Compounds and uses thereof for decreasing activity of hormone-sensitive lipase
  申请人：——

  公开号：US20030166644A1

  公开（公告）日：2003-09-04

  Use of compounds to inhibit hormone-sensitive lipase, pharmaceutical compositions comprising the compounds, methods of treatment employing these compounds and compositions, and novel compounds. The present compounds are inhibitors of hormone-sensitive lipase and may be useful in the treatment and/or prevention of medical disorders where a decreased activity of hormone-sensitive lipase is desirable.

  使用化合物抑制激素敏感性脂肪酶，包括这些化合物的药物组合物，使用这些化合物和组合物的治疗方法，以及新化合物。目前的化合物是激素敏感性脂肪酶的抑制剂，可能在治疗和/或预防需要降低激素敏感性脂肪酶活性的医学疾病中有用。
• Cooperative Mn(<scp>i</scp>)-complex catalyzed transfer hydrogenation of ketones and imines
  作者：Kasturi Ganguli、Sujan Shee、Dibyajyoti Panja、Sabuj Kundu

  DOI：10.1039/c8dt05001e

  日期：——

  complex presented higher reactivity in the transfer hydrogenation (TH) of ketones in 2-propanol. Experimentally, it was established that both the benzimidazole and amine N–H proton played a vital role in the enhancement of the catalytic activity. Utilizing this system a wide range of aldehydes and ketones were reduced efficiently. Notably, the TH of several imines, as well as chemoselective reduction of

  据报道，带有双功能配体的Mn（I）配合物的合成和反应性均包含胺N-H和苯并咪唑片段。在各种配体中，含Mn（I）的N -（（1 H-苯并咪唑-2-基）甲基）苯胺配体）配合物在2-丙醇中酮的转移加氢（TH）中表现出更高的反应性。实验确定，苯并咪唑和胺NH质子均在增强催化活性中起着至关重要的作用。使用该系统可以有效地减少各种醛类和酮类。值得注意的是，在该催化剂的存在下，实现了几种亚胺的TH以及不饱和酮的化学选择性还原。进行DFT计算以了解合理的反应机理，该机理揭示了转移氢化反应遵循协调的外球机理。
• Synthesis and Evaluation of Selected Benzimidazole Derivatives as Potential Antimicrobial Agents
  作者：Fatmah Alasmary、Anna Snelling、Mohammed Zain、Ahmed Alafeefy、Amani Awaad、Nazira Karodia

  DOI：10.3390/molecules200815206

  日期：——

  A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed

  合成了53个苯并咪唑衍生物的文库，它们在1、2和5位具有取代基，并针对一系列与医学相关的细菌和真菌参考菌株进行了筛选。SAR分析最有前景的结果表明，化合物的抗菌活性取决于与双环杂环相连的取代基。特别是，某些化合物对两种耐甲氧西林的金黄色葡萄球菌（MRSA）菌株表现出抗菌活性，其最低抑制浓度（MIC）与广泛使用的环丙沙星药物相当。这些化合物具有一些共同特征。三个具有5-卤素取代基；两个是（S）-2-乙胺苯并咪唑的衍生物；其他是一种2-（氯甲基）-1H-苯并[d]咪唑和（1H-苯并[d]咪唑-2-基）甲硫醇的衍生物。抗真菌筛选的结果也非常有趣：23种化合物对选定的真菌菌株显示出有效的杀真菌活性。它们的MIC值显示出比两性霉素B相同或更高的效力。5-卤代苯并咪唑衍生物被认为是有前途的广谱抗微生物候选物，值得进一步研究以用于潜在的治疗应用。
• Aminopyrimidine Kinase Inhibitors
  申请人：Baldino Carmen M.

  公开号：US20110152235A1

  公开（公告）日：2011-06-23

  Disclosed are compounds, pharmaceutical compositions containing those compounds, and uses of the compounds and compositions as modulators of casein kinase 1 (e.g., CK1γ), casein kinase 2 (CK2), Pim 1, Pim2, Pim3, the TGFβ pathway, the Wnt pathway, the JAK/STAT pathway, and/or the mTOR pathway. Uses are also disclosed for the treatment or prevention of a range of therapeutic indications due at least in part to aberrant physiological activity of casein kinase 1 (e.g., CK1γ), casein kinase 2 (CK2), Pim 1, Pim2, Pim3, the TGFβ pathway, the Wnt pathway, the JAK/STAT pathway, and/or the mTOR pathway.

  揭示了化合物、含有这些化合物的药物组合物，以及这些化合物和组合物作为酪蛋白激酶1（例如CK1γ）、酪蛋白激酶2（CK2）、Pim 1、Pim2、Pim3、TGFβ途径、Wnt途径、JAK/STAT途径和/或mTOR途径调节剂的用途。还揭示了用于治疗或预防一系列治疗适应症的用途，至少部分原因是由于酪蛋白激酶1（例如CK1γ）、酪蛋白激酶2（CK2）、Pim 1、Pim2、Pim3、TGFβ途径、Wnt途径、JAK/STAT途径和/或mTOR途径的异常生理活性。
• Synthesis and Characterization of Novel Oxadiazole Derivatives from Benzimidazole
  作者：Balasubramanaya Vishwanathan、Bannimath Gurupadayya

  DOI：10.5012/jkcs.2014.58.5.450

  日期：2014.10.20

  (4a−4j) were efficiently synthesized. Condensation of hydrazide derivative 3 with various carboxylic acid derivatives yielded N-[(1H-benzo[d]imidazol-2-yl)methy](5-substituted-1,3,4-oxadiazol-2-yl)methanamine (4a−4j) and compound 5-[(1H-benzo[d]imidazol-2-yl)methylamino]methyl}-1,3,4-oxadiazole-2-thiol (4k) was obtained on treating hydrazide 3 with carbon disulfide. All the newly synthesized analogues

  在本研究中，一系列新的N-（1H-苯并[d]咪唑-2-基）甲基-5-[（杂）芳基-1,3,4-恶二唑-2-基]甲胺（4a-4j）被有效地合成了。酰肼衍生物3与各种羧酸衍生物的缩合产生N-[（1H-苯并[d]咪唑-2-基）甲基]（5-取代的1,3,4-恶二唑-2-基）甲胺（4a- 4j）和化合物5-[（（1H-苯并[d]咪唑-2-基）甲基氨基]甲基] -1,3,4-恶二唑-2-硫醇（4k））通过用二硫化碳处理酰肼3而获得。所有新合成的类似物均通过IR，1 H NMR，C NMR和质谱数据表征。