苯并咪唑-7-羧酸甲酯 | 37619-25-3

• 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: 苯并咪唑-7-羧酸甲酯
• 中文别名: 1H-苯并[D]咪唑-4-羧酸甲酯；4-苯并咪唑羧酸甲酯；1H -苯并[D]咪唑- 4 -羧酸甲酯
• 英文名称: methyl 1H-benzo[d]imidazole-4-carboxylate
• 英文别名: methyl 1H-benzimidazole-4-carboxylate
• CAS: 37619-25-3
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: UZMYAXZLWVFGBD-UHFFFAOYSA-N

物化性质

• 沸点：
  416.2±18.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 1,3-benzodiazole-4-carboxylate
Synonyms: Methyl 1,3-benzodiazole-7-carboxylate

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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: Methyl 1,3-benzodiazole-4-carboxylate
CAS number: 37619-25-3

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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: C9H8N2O2
Molecular weight: 176.2

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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

反应信息

• 作为反应物：
  描述：

  苯并咪唑-7-羧酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以79.4%的产率得到1H-苯并咪唑-4-基甲醇
  参考文献：
  名称：

  一种亚胺类IDO抑制剂及其制备与用途

  摘要：

  本发明涉及一种亚胺类IDO抑制剂，它们的制备与治疗用途，所述亚胺类IDO抑制剂包括式I所示的亚胺类化合物或其药学上可接受的盐，其可以用作抗肿瘤免疫治疗药剂，式I所示取代基如说明书中描述，本发明的IDO抑制剂特点在于：作为IDO抑制剂，在细胞水平上的活性优异，其IC50小于1μM。

  公开号：

  CN114835621A
• 作为产物：
  描述：

  苯并咪唑-4-羧酸 在 硫酸 作用下， 以 甲醇 为溶剂， 以82%的产率得到苯并咪唑-7-羧酸甲酯
  参考文献：
  名称：

  一种苯并咪唑衍生物BI308及其制备方法和应用

  摘要：

  本发明公开了一种苯并咪唑衍生物BI308及其制备方法，其化学命名为甲基1‑[(2R,3R,4S,5R)‑3,4‑二羟基‑5‑(羟甲基)四氢呋喃‑2‑基]‑1H苯并[d]咪唑‑4‑羧酸酯。本发明的苯并咪唑衍生物及其药学上可接受的盐、溶剂化物和水合物对MCF‑7、SK‑BR‑3、HCT 116、U‑118 MG、U‑87 MG、MDA‑MB‑468具有优秀的抗肿瘤体内外活性，在制备抗肿瘤药物的上具有较好的应用前景。

  公开号：

  CN112920241A

文献信息

• Diversified facile synthesis of benzimidazoles, quinazolin-4(3H)-ones and 1,4-benzodiazepine-2,5-diones via palladium-catalyzed transfer hydrogenation/condensation cascade of nitro arenes under microwave irradiation
  作者：Kaicheng Zhu、Jian-Hong Hao、Cheng-Pan Zhang、Jiajun Zhang、Yiqing Feng、Hua-Li Qin

  DOI：10.1039/c4ra15765f

  日期：——

  An efficient methodology for diversified preparation of benzimidazole, quinazolin-4(3H)-ones and 1,4-benzodiazepine-2,5-diones is established using a Pd-CTH/condensation cascade of nitro arenes in a TEA–formic acid mixture under microwave irradiation.

  一种高效的方法学已建立，用于在微波辐射下利用Pd-CTH/缩合级联反应在TEA-甲酸混合物中多样化制备苯并咪唑、喹唑啉-4(3H)-酮和1,4-苯二氮杂环己酮。
• [EN] BIPHENYL SUBSTITUTED 1,3-DIHYDRO-BENZOIMIDAZOL-2-YLIDENEAMINE DERIVATIVES<br/>[FR] DÉRIVÉS DE 1,3-DIHYDRO-BENZOIMIDAZOL-2-YLIDÈNE-AMINE À SUBSTITUTION BIPHÉNYLE
  申请人：NOVARTIS AG

  公开号：WO2011157787A1

  公开（公告）日：2011-12-22

  The invention relates to new derivatives of formula (I), wherein the substituents are as defined in the specification; to processes for the preparation of such derivatives; pharmaceutical compositions comprising such derivatives; such derivatives as a medicament; such derivatives for the treatment of one or more IGF-1 R mediated disorders or diseases.

  这项发明涉及公式（I）的新衍生物，其中取代基如规范中所定义；制备这种衍生物的方法；包括这种衍生物的药物组合物；将这种衍生物用作药物；将这种衍生物用于治疗一个或多个IGF-1 R介导的疾病。
• [EN] THIADIAZOLYL DERIVATIVES AS DNA POLYMERASE THETA INHIBITORS<br/>[FR] DÉRIVÉS DE THIADIAZOLYLE COMME INHIBITEURS DE L'ADN POLYMÉRASE THÊTA
  申请人：IDEAYA BIOSCIENCES INC

  公开号：WO2020243459A1

  公开（公告）日：2020-12-03

  Disclosed herein are certain thiadiazolyl derivatives Formula (I): that inhibit DNA Polymerase Theta (Polθ) activity, in particular inhibit Polθ activity by inhibiting ATP dependent helicase domain activity of Polθ. Also, disclosed are pharmaceutical compositions comprising such compounds and methods of treating and/or preventing diseases treatable by inhibition of Polθ such as cancer, including homologous recombination (HR) deficient cancers.

  本文披露了某些噻二唑基衍生物 Formula (I)：它们通过抑制 DNA 聚合酶 Θ（Polθ）活性来抑制 Polθ 活性，特别是通过抑制 Polθ 的 ATP 依赖螺旋酶结构域活性来抑制 Polθ 活性。此外，还披露了包括这些化合物的药物组合物以及治疗和/或预防通过抑制 Polθ 而可治疗的疾病的方法，如癌症，包括同源重组（HR）缺陷癌症。
• Mild and General One-Pot Reduction and Cyclization of Aromatic and Heteroaromatic 2-Nitroamines to Bicyclic 2H-Imidazoles
  作者：Emily Hanan、Bryan Chan、Anthony Estrada、Daniel Shore、Joseph Lyssikatos

  DOI：10.1055/s-0030-1259007

  日期：2010.11

  A one-pot procedure for the conversion of aromatic and heteroaromatic 2-nitroamines into bicyclic 2H-benzimidazoles is described. The procedure employs formic acid, iron powder, and an additive such as NH4Cl to reduce the nitro group and effect the imidazole cyclization with high-yielding conversions generally within one to two hours. The compatibility with a wide range of functionality demonstrates the general utility of this procedure.

  描述了一种将芳香和杂芳香2-硝基胺转化为双环2H-苯并咪唑的一锅法步骤。该步骤采用甲酸、铁粉以及NH4Cl等添加剂来还原硝基并实现咪唑环化，通常在一到两小时内完成高产率的转化。其广泛的官能团兼容性显示了该步骤的普遍实用性。
• Deprotection of N-benzylbenzimidazoles and N-benzylimidazoles with triethylsilane and Pd/C
  作者：Thomas H. Graham

  DOI：10.1016/j.tetlet.2015.03.127

  日期：2015.5

  The benzyl group is a protecting group for benzimidazoles and imidazoles that can survive acidic, basic, oxidizing, and reducing conditions. Deprotection, however, can require vigorous and potentially non-chemoselective methods. The triethylsilane–Pd/C reduction system is an exceptionally mild, convenient, and efficient method for deprotecting N-benzylbenzimidazoles that are unsubstituted at the 2-

  苄基是苯并咪唑和咪唑的保护基，可以在酸性，碱性，氧化和还原条件下存活。然而，脱保护可能需要有力的并且可能是非化学选择性的方法。三乙基硅烷-Pd / C还原系统是一种非常温和，方便，有效的方法，用于保护在2位和4位未被取代的N-苄基苯并咪唑以及适当取代的N-苄基咪唑。