苯并咪唑-5-羧酸甲酯 | 26663-77-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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-5-羧酸甲酯
• 中文别名: 苯并[D]咪唑-5-羧酸甲酯；苯并咪唑-5-甲酸甲酯
• 英文名称: methyl 1H-benzo[d]imidazole-5-carboxylate
• 英文别名: methyl 1H-benzimidazole-5-carboxylate；methyl benzimidazole-5-carboxylate；5-benzimidazolecarboxylic acid,methyl ester；methyl 3H-benzimidazole-5-carboxylate
• CAS: 26663-77-4
• 化学式: C₉H₈N₂O₂
• mdl: MFCD03407310
• 分子量: 176.175
• InChiKey: WJHHIVYNOVTVGY-UHFFFAOYSA-N

物化性质

• 熔点：
  139 °C
• 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)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 安全说明：
  S24/25
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Name:	Methyl 1h-benzimidazole-5-carboxylate, 97% Material Safety Data Sheet
Synonym:
CAS:	26663-77-4

Section 1 - Chemical Product MSDS Name: Methyl 1h-benzimidazole-5-carboxylate, 97% Material Safety Data Sheet
Synonym:

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
26663-77-4	Methyl 1H-benzimidazole-5-carboxylate	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Not available. Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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. Store under nitrogen.

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SECTION 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 26663-77-4: 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
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C9H8N2O2
Molecular Weight: 176.17

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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, acids.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 26663-77-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 1H-benzimidazole-5-carboxylate - 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 No information available. IMO No information available. RID/ADR No information available.

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SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases: S 24/25 Avoid contact with skin and eyes. WGK (Water Danger/Protection) CAS# 26663-77-4: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 26663-77-4 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 26663-77-4 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 6/10/2003 Revision #0 Date: Original. The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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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-5-羧酸甲酯 在 甲醇 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到1H-苯并咪唑-5-羧酸
  参考文献：
  名称：

  [EN] SELECTIVE HDAC3 INHIBITORS
  [FR] INHIBITEURS HDAC3 SÉLECTIFS

  摘要：

  本文提供了HDAC3抑制剂，以及包括将这些化合物用于需要的受试者的治疗方法。

  公开号：

  WO2014121062A1
• 作为产物：
  描述：

  1H-苯并咪唑-5-羧酸 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以489 mg的产率得到苯并咪唑-5-羧酸甲酯
  参考文献：
  名称：

  [EN] ARYL AND HETEROARYL-CARBOXAMIDE SUBSTITUTED HETEROARYL COMPOUNDS AS TYK2 INHIBITORS
  [FR] COMPOSÉS HÉTÉROARYLE SUBSTITUÉS PAR ARYLE ET HÉTÉROARYLE-CARBOXAMIDE UTILES EN TANT QU'INHIBITEURS DE TYK2

  摘要：

  公开了一种化合物，其为新颖的羧酰胺取代化合物，化学式为（I）；以及其制备方法，包含它们的药物组成物和它们作为酪氨酸激酶2（Tyk2）抑制剂在治疗中的用途。

  公开号：

  WO2021204626A1

文献信息

• Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazoles <i>via</i> a sulfinyl radical
  作者：Mei Fu、Xiaochen Ji、Yongtong Li、Guo-Jun Deng、Huawen Huang

  DOI：10.1039/d0gc02269a

  日期：——

  A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to

  发现温和的不含过渡金属的无毒需氧光氧化还原系统可实现2-巯基苯并咪唑的高效脱硫。这种可行的催化系统包括低催化剂含量的Rose Bengal作为光敏剂，以及廉价的无毒NaCl（催化量）作为添加剂，并与氧气气氛相结合。该方案提供了重要的替代途径，可以以通常的高收率获得各种苯并咪唑和氘代苯并咪唑产品，并且对各种合成和药学上有用的功能具有良好的耐受性。机理研究表明，单电子转移和能量转移都可能在初始步骤发生，并且亚硫酰基自由基中间体参与了关键的脱硫过程。
• Efficient N-arylation of azole compounds utilizing selective aryl-transfer TMP-iodonium(III) reagents
  作者：Daichi Koseki、Erika Aoto、Toshitaka Shoji、Kazuma Watanabe、Yasuko In、Yasuyuki Kita、Toshifumi Dohi

  DOI：10.1016/j.tetlet.2019.04.012

  日期：2019.5

  It was determined that diaryliodonium(III) triflates bearing a trimethoxybenzene (TMP) auxiliary are more reactive than the reported selective aryl-transfer iodonium salts in the N-arylation of benzimidazoles and other types of azole compounds under catalytic conditions. The TMP-iodonium(III) salts can thus effectively facilitate the reaction at 50 °C or below, producing the corresponding N-arylated

  已确定在催化条件下，在苯并咪唑和其他类型的唑化合物的N-芳基化反应中，带有三甲氧基苯（TMP）助剂的二芳基碘鎓（III）三氟甲磺酸盐比报道的选择性芳基转移碘鎓盐更具反应性。因此，TMP-碘鎓（III）盐可以有效地促进在50℃或更低的温度下反应，产生相应的N-芳基化的联芳基，而不会形成TMP-衍生的偶联副产物。在温和的条件下使用该TMP试剂可防止潜在的辅助基团参与偶联反应的问题，这是在使用需要升高温度的碘鎓（III）盐时观察到的。
• Non-prostanoid thromboxane A2 receptor antagonists with a dibenzoxepin ring system. 2
  作者：Etsuo Ohshima、Hitoshi Takami、Hideyuki Sato、Shinichiro Mohri、Hiroyuki Obase、Ichiro Miki、Akio Ishii、Shiro Shirakura、Akira Karasawa、Kazuhiro Kubo

  DOI：10.1021/jm00096a017

  日期：1992.9

  11-[2-(1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxep in-2- carboxylic acid derivatives and related compounds were synthesized and found to be potent TXA2/PGH2 receptor antagonists. Each compound synthesized was tested for its ability to displace [3H]U-46619 binding from guinea pig platelet TXA2/PGH2 receptors. Structure-activity relationship studies revealed that the following key elements were

  合成了一系列11- [2-（1-苯并咪唑基）亚乙基] -6,11-二氢二苯并[b，e] oxep in-2-羧酸衍生物及相关化合物，发现它们是有效的TXA2 / PGH2受体拮抗剂。测试了每种合成的化合物从豚鼠血小板TXA2 / PGH2受体置换[3H] U-46619结合的能力。构效关系研究表明，增强活性需要以下关键元素：（1）在二苯并二甲苯环系统的11位上的（E）-2-（1-苯并咪唑基）亚乙基侧链和（2）a在二苯并二氧杂戊环体系的2-位上的羧基。研究还表明，该系列化合物在豚鼠血小板中与TXA2 / PGH2受体的结合亲和力与人血小板中的相关性较弱。将取代基引入苯并咪唑部分是有效的，并且（E）-11- [2-（5,6-二甲基-1-苯并咪唑基）亚乙基]钠-6,11-二氢二苯并[b，e] oxepin-2 -羧酸一水合物（57）对人血小板TXA2 / PGH2受体的亲和力最高，K（i）值为1
• Rapid Access to Benzimidazo[1,2-<i>a</i>]quinoline-Fused Isoxazoles via Pd(II)-Catalyzed Intramolecular Cross Dehydrogenative Coupling: Synthetic Versatility and Photophysical Studies
  作者：Subrata Sahoo、Shantanu Pal

  DOI：10.1021/acs.joc.0c02926

  日期：2021.3.5

  efficient and atom-economical palladium-catalyzed intramolecular cross dehydrogenative coupling (CDC) reaction has been developed for the construction of highly π-conjugated benzimidazo[1,2-a]quinoline-fused isoxazole scaffolds using molecular oxygen as sole oxidant. The approach portrayed wide substrate scope with good functional group tolerance and depicted a useful tool for the generation of fluorescence

  已开发出一种有效且原子经济的钯催化的分子内交叉脱氢偶联（CDC）反应，用于使用分子氧作为唯一氧化剂构建高度π共轭的苯并咪唑并[1,2- a ]喹啉稠合的异恶唑支架。该方法描绘了具有良好官能团耐受性的较宽的底物范围，并描述了一种用于生成具有高量子产率的荧光活性化合物的有用工具。已经展示了通过Fe催化的还原异恶唑环裂解为吡啶，嘧啶，吡唑稠合的杂环化合物的方法的通用性。
• Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides
  作者：Liangliang Luo、Hongyan Li、Jinxin Liu、Yuan Zhou、Lin Dong、You-Cai Xiao、Fen-Er Chen

  DOI：10.1039/d0ra04636a

  日期：——

  A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved.

  一种高效的TMSCl介导的N-亲核试剂加成到异氰酸酯的方法已经实现。