2-呋喃硼酸 | 4347-32-4

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-呋喃硼酸
• 中文别名: 3-醛基-4-噻吩硼酸
• 英文名称: 4-formyl-3-thiopheneboronic acid
• 英文别名: (4-formylthiophen-3-yl)boronic acid；4-formylthiophene-3-boronic acid；3-Formyl-4-thiopheneboronic acid
• CAS: 4347-32-4
• 化学式: C₅H₅BO₃S
• mdl: MFCD01319006
• 分子量: 155.97
• InChiKey: LVLCWVAVXNPOFF-UHFFFAOYSA-N

物化性质

• 沸点：
  381.2±52.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 储存条件：
  0-6°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Formyl-4-thiopheneboronic acid
Synonyms: (4-Formyl-3-thienyl)boronic acid

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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: 3-Formyl-4-thiopheneboronic acid
CAS number: 4347-32-4

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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, under −20◦C.
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: C5H5BO3S
Molecular weight: 156.0

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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, 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：

  2-呋喃硼酸 在 肼 作用下， 生成 2H-thieno[3,4-d][1,2,3]diazaborinin-1-ol
  参考文献：
  名称：

  Gronowitz,S.; Bugge,A., Acta Chemica Scandinavica (1947), 1965, vol. 19, p. 1271 - 1285

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴-4-噻吩甲醛乙烯缩醛 在 正丁基锂 、 盐酸 、 水 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 以95%的产率得到2-呋喃硼酸
  参考文献：
  名称：

  WO2006/46030

  摘要：

  公开号：

文献信息

• Direct One-Pot Synthesis of Naphthoxindoles from 4-Bromooxindoles by Suzuki-Miyaura Coupling and Aldol Condensation Reactions
  作者：Kyeong-Yong Park、Bum Tae Kim、Jung-Nyoung Heo

  DOI：10.1002/ejoc.201301242

  日期：2014.1

  An efficient one-pot synthesis of naphthoxindoles by using 4-bromoindolin-2-ones and 2-formylphenylboronic acids has been developed. The coupling reaction proceeds in good to excellent yields under microwave irradiation through a Suzuki–Miyaura coupling and an aldol condensation cascade reaction. In addition, this protocol permits the facile construction of naphthoxindoles through an expanded scope

  使用 4-bromoindolin-2-ones 和 2-formylphenylboronic 酸有效地一锅合成萘并吲哚。在微波辐射下，通过 Suzuki-Miyaura 偶联和醇醛缩合级联反应，偶联反应以良好的产率进行。此外，该协议允许通过扩大的底物范围轻松构建萘并吲哚。
• Discovery of a potent, highly selective, and orally bioavailable inhibitor of CDK8 through a structure-based optimisation
  作者：Mingfeng Yu、Yi Long、Yuchao Yang、Manjun Li、Theodosia Teo、Benjamin Noll、Stephen Philip、Shudong Wang

  DOI：10.1016/j.ejmech.2021.113391

  日期：2021.6

  is viewed as a therapeutic target for the treatment of the disease. Accordingly, the search for small-molecule inhibitors of CDK8 is being intensified. Capitalising on our initial discovery of AU1-100, a potent CDK8 inhibitor yet with a limited degree of kinase selectivity, a structure-based optimisation was carried out, with a series of new multi-substituted pyridines rationally designed, chemically

  CDK8 在多种类型的人类癌症中失调，被视为治疗该疾病的治疗靶点。因此，正在加紧寻找 CDK8 的小分子抑制剂。利用我们最初发现的 AU1-100，一种有效的 CDK8 抑制剂，但激酶选择性有限，我们进行了基于结构的优化，对一系列新的多取代吡啶进行了合理设计、化学制备和生物学评估。这种努力最终确定了42，这是一种更有效的 CDK8 抑制剂，具有优异的运动学选择性和口服生物利用度。42抗增殖作用的机制对 MV4-11 细胞进行了研究，表明该化合物可以阻止 G1 细胞周期并引发细胞凋亡。估计42的肝毒性和心脏毒性的风险较低。这些发现值得进一步研究42作为靶向癌症治疗剂。
• Simple <i>Aza</i>-Conjugate Addition Methodology for the Synthesis of Isoindole Nitrones and 3,4-Dihydroisoquinoline Nitrones
  作者：Lucy R. Peacock、Robert S. L. Chapman、Adam C. Sedgwick、Mary F. Mahon、Dominique Amans、Steven D. Bull

  DOI：10.1021/acs.orglett.5b00103

  日期：2015.2.20

  reactive N-hydroxy-carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford isoindole nitrones and 3,4-dihydroisoquinoline nitrones in good yield. Conditions have been developed to reduce these isoindole nitrones to their corresponding hydroxylamine, enamine, and amine derivatives. Isoindole nitrones react with dimethyl acetylenedicarboxylate (DMAD) via a [4

  含有邻位取代的α，β-不饱和羧酸衍生物的芳醛与羟胺反应，以提供反应性的N-羟基-甲醇胺中间体，使它们进行分子内的氮杂-共轭加成反应，从而以高收率获得异吲哚腈和3,4-二氢异喹啉腈。已经开发了将这些异吲哚腈还原为它们相应的羟胺，烯胺和胺衍生物的条件。异吲哚硝酮通过[4 + 2]-环加成/脱氨基途径与乙酰二甲酸二甲酯（DMAD）反应，得到取代的萘衍生物，而3,4-二氢异喹啉硝酮通过[1,3]-偶极环加成途径与DMAD反应，得到萘衍生物。三环杂芳烃。
• Total Synthesis of Aristolactams via a One-Pot Suzuki−Miyaura Coupling/Aldol Condensation Cascade Reaction
  作者：Joa Kyum Kim、Young Ha Kim、Ho Tae Nam、Bum Tae Kim、Jung-Nyoung Heo

  DOI：10.1021/ol801291k

  日期：2008.8.21

  A direct one-pot synthesis of phenanthrene lactams, which employs a Suzuki-Miyaura coupling/aldol condensation cascade reaction of isoindolin-1-one with 2-formylphenylboronic acid, has been developed. The approach is used to efficiently produce a number of natural aristolactams, such as aristolactam BII (cepharanone B), aristolactam BIII, aristolactam FI (piperolactam A), N-methyl piperolactam A, and

  已经开发了一种直接一锅合成菲内酰胺的方法，该方法利用了异吲哚啉-1-酮与2-甲酰基苯基硼酸的Suzuki-Miyaura偶联/醛醇缩合级联反应。该方法用于有效地生产许多天然的马兜铃内酰胺，例如马兜铃内酰胺BII（头孢兰酮B），马兜铃内酰胺BIII，马兜铃内酰胺FI（哌内酰胺A），N-甲基哌内酰胺A和sauristolactam。
• [EN] MITOCHONDRIAL ALDEHYDE DEHYDROGENASE 2 (ALDH2) BINDING POLYCYCLIC AMIDES AND THEIR USE FOR THE TREATMENT OF CANCER<br/>[FR] AMIDES POLYCYCLIQUES SE LIANT À L'ALDÉHYDE DÉSHYDROGÉNASE 2 (ALDH2) MITOCHONDRIALE ET LEUR UTILISATION DANS LE TRAITEMENT DU CANCER
  申请人：ALDEA PHARMACEUTICALS INC

  公开号：WO2015127137A1

  公开（公告）日：2015-08-27

  The present invention provides compounds of formula I that bind to mitochondrial aldehyde dehydrogenase-2 (ALDH2), and methods of using said compounds to treat patients with i.a. cancer, Fanconi anemia and alcohol-related disorders. [Formula should be inserted here] wherein i.a. A is O or NH; RA is H, cycloalkyl or alkyl optionally substituted with a carbocycle; X1 and X2 are N or CH; R1, R2, R3 and R4 are H; and Z is an optionally substituted 5- or 6-membered aromatic ring.

  本发明提供了化合物I的公式，该化合物与线粒体醛脱氢酶-2（ALDH2）结合，并且使用这些化合物的方法来治疗患有癌症、范可尼贫血和与酒精相关疾病的患者。其中i.a. A为O或NH；RA为H，环烷基或烷基，可选地用碳环取代；X1和X2为N或CH；R1、R2、R3和R4为H；Z为一个可选取代的5-或6-成员芳香环。