苯并二唑-4-甲醛 | 32863-32-4

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 中文名称: 苯并二唑-4-甲醛
• 中文别名: 2,1,3-苯并恶二唑-4-甲醛；5-硝基-1H-吲哚；苯并噁二唑-4-甲醛
• 英文名称: benzo[c][1,2,5]oxadiazole-4-carbaldehyde
• 英文别名: 4-benzofurazancarboxaldehyde；2,1,3-benzoxadiazole-4-carbaldehyde
• CAS: 32863-32-4
• 化学式: C₇H₄N₂O₂
• mdl: MFCD07772900
• 分子量: 148.121
• InChiKey: YBBRQAXNTWMMFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  100-102°C
• 沸点：
  277 °C
• 密度：
  1.417
• 闪点：
  121 °C
• 溶解度：
  可溶于二氯甲烷（少许）、氯仿（少许）、甲醇（少许）

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：
  0.0
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8℃，在惰性气体氛围下进行。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Benzofurazancarboxaldehyde
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-Benzofurazancarboxaldehyde
CAS number: 32863-32-4

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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, refrigerated.
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: C7H4N2O2
Molecular weight: 148.1

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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：

  苯并二唑-4-甲醛 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以57%的产率得到benzofurazan-4-carboxylic acid
  参考文献：
  名称：

  一种伊拉地平杂质Ⅱ的制备方法

  摘要：

  本发明公开了一种伊拉地平杂质Ⅱ的制备方法，其特征在于：以苯并噁二唑‑4‑甲醛为原料，在碱性有机条件下发生歧化反应，经分离得到伊拉地平杂质Ⅱ，反应式如下：该伊拉地平杂质Ⅱ制备工艺简单，原料易得，所得产品纯度高(HPLC≥99％)，可直接用于伊拉地平关键中间体(化合物2)的质量研究。

  公开号：

  CN106967006A
• 作为产物：
  描述：

  7 - 甲基-1H -苯并[D]咪唑 在 四氯化碳 、 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 过氧化苯甲酰 作用下， 以 二甲基亚砜 为溶剂， 生成 苯并二唑-4-甲醛
  参考文献：
  名称：

  一种制备含有苯并呋咱环类抗高血压药物的合 成方法

  摘要：

  本发明涉及一种制备含有呋咱环类抗高血压药物的合成方法，以4-甲基苯并呋咱为原料，经溴化、氧化反应制备重要中间体4-甲酰基苯并呋咱、再与乙酰乙酸酯发生Hantzsch反应制备目标化合物。本发明与其它工艺相比，它具有反应条件温和，操作简单，高效，收率高等特点，具有一定的工业化生产前景。

  公开号：

  CN102285978B

文献信息

• A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH₂ OH) to Nitriles (RCN) Mediated by SO₂ F₂
  作者：Ying Jiang、Bing Sun、Wan-Yin Fang、Hua-Li Qin

  DOI：10.1002/ejoc.201900478

  日期：2019.6.2

  A new transition‐metal‐free one‐pot cascade process for the direct conversion of alcohols to nitriles was developed without introducing an “additional carbon atom”. This protocol allows transformations of readily available, inexpensive, and abundant alcohols to highly valuable nitriles.

  在不引入“额外碳原子”的情况下，开发了一种新的无过渡金属的单锅级联工艺，用于将醇直接转化为腈。该方案允许将容易获得，廉价和丰富的醇转化为高价值的腈。
• 化合物及其作为L-型钙通道阻滞剂或/和乙酰 胆碱酯酶抑制剂的应用
  申请人：江苏先声药物研究有限公司

  公开号：CN102464608B

  公开（公告）日：2016-05-11

  本发明公开了化合物及其作为L-型钙通道阻滞剂或/和乙酰胆碱酯酶抑制剂的应用。100nmol/L的本发明所述化合物对L-型钙通道的抑制率为8.71-35.77％，1000nmol/L的本发明所述化合物对L-型钙通道的抑制率为26.43-83.54％，本发明所述化合物对乙酰胆碱酯酶活性的IC50为16-1470nmol/L，可见，本发明所述化合物对L-型钙通道具有有效地阻滞作用，对乙酰胆碱酯酶具有明显的抑制作用，因此，本发明还提供所述化合物在制备治疗心血管疾病、中风或老年性痴呆药物中的应用。
• A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO ₂ F ₂ /K ₂ CO ₃ Using DMSO as Solvent and Oxidant
  作者：Gao‐Feng Zha、Wan‐Yin Fang、Jing Leng、Hua‐Li Qin

  DOI：10.1002/adsc.201900104

  日期：2019.5.14

  A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture‐ and oxygen‐free conditions are required. Stoichiometric amount of inexpensive K2CO3, which generates easy to separate by‐products, is used as the base. Thus, 5‐gram

  在环境温度下，使用SO 2 F 2作为亲电子试剂在DMSO中作为氧化剂和溶剂，伯醇和仲醇进行实用，通用且温和的氧化成羰基化合物的收率可达99％。不需要无湿气和无氧条件。化学计量的廉价K 2 CO 3生成易于分离的副产物的油基用作基础。因此，通过简单的过滤作为后处理，以几乎定量的产量进行了5克规模的运行。还应注意使用通常促进竞争的Pummerer重排的极性溶剂（例如DMSO）。该协议与（杂）芳烃，烯烃和炔烃底物上的各种常见的N-，O-和S-官能团兼容（68个例子）。该方案被应用（99％的产率）用于重要的降胆固醇药物瑞舒伐他汀的正式合成。
• Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH₂OH/Na₂CO₃/SO₂F₂ in DMSO
  作者：Wan-Yin Fang、Hua-Li Qin

  DOI：10.1021/acs.joc.8b03164

  日期：2019.5.3

  and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and

  使用无机试剂（NH 2 OH / Na 2 CO ）开发了一种简单，温和且实用的方法，将醛直接转化为腈，可在较宽的底物范围内实现出色的官能团耐受性（52个实例，大多数情况下产率超过90％）3 / SO 2 F 2）在DMSO中。该方法允许以易用，原子和步经济的方式将易于获得，廉价且丰富的醛转化为高度有价值的腈，而无需过渡金属。该协议将作为将氰基部分安装到复杂分子的强大工具。
• 4,6-Substituted-1H-Indazoles as potent IDO1/TDO dual inhibitors
  作者：Lingling Yang、Yang Chen、Junlin He、Emmanuel Mfotie Njoya、Jianjun Chen、Siyan Liu、Congqiang Xie、Wenze Huang、Fei Wang、Zhouyu Wang、Yuzhi Li、Shan Qian

  DOI：10.1016/j.bmc.2019.02.014

  日期：2019.3

  Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO) are constitutively overexpressed in many types of cancer cells and exert important immunosuppressive functions. In this article, a series of 4,6-substituted-1H-indazole derivatives were synthesized and evaluated the inhibitory activities against IDO1 and TDO, as well as their structure-activity relationships (SARs). Among these

  吲哚胺 2,3-双加氧酶 1 (IDO1) 和色氨酸 2,3-双加氧酶 (TDO) 在许多类型的癌细胞中组成型过度表达并发挥重要的免疫抑制功能。在本文中，合成了一系列 4,6-取代-1H-吲唑衍生物并评估了对 IDO1 和 TDO 的抑制活性，以及​​它们的构效关系 (SAR)。其中，化合物 35 显示出最强的 IDO1 抑制效力，在酶促测定中的 IC50 值为 0.74 μM，在 HeLa 细胞中的 IC50 值为 1.37 μM。蛋白质印迹结果的定量分析表明，35 以浓度依赖性方式显着降低 INFγ 诱导的 IDO1 表达。此外，35 显示出有希望的 TDO 抑制，在酶促测定中的 IC50 值为 2.93 μM，在 A172 细胞中为 7.54 μM。而且，化合物35在CT26异种移植模型中表现出体内抗肿瘤活性。这些发现表明 1H-吲唑衍生物 35 是一种有效的 IDO1/TDO 双重抑制剂，具有开发用于