苯并噻吩-3-羧酸甲酯 | 22913-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 苯并噻吩-3-羧酸甲酯
• 中文别名: 苯并噻吩-3-甲酸甲酯
• 英文名称: methyl benzothiophene-3-carboxylate
• 英文别名: benzo[b]thiophene-3-carboxylic acid methyl ester；3-carboxymethylbenzothiophene；methyl benzo[b]thiophene-3-carboxylate；benzo[b]thiophene-3-carboxylic acid methyl ester；Benzo[b]thiophen-3-carbonsaeure-methylester；methyl benzothiophene-3-carboxylate；methyl 1-benzothiophene-3-carboxylate
• CAS: 22913-25-3
• 化学式: C₁₀H₈O₂S
• mdl: MFCD06203855
• 分子量: 192.238
• InChiKey: FSJAXBXCHWMNAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl benzothiophene-3-carboxylate
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: Methyl benzothiophene-3-carboxylate
CAS number: 22913-25-3

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H8O2S
Molecular weight: 192.2

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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, 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：

  苯并噻吩-3-羧酸甲酯 在 sodium hydroxide 、 氢气 作用下， 以 水 为溶剂， 反应 1.5h， 生成 1-苯并噻吩-3-羧酸
  参考文献：
  名称：

  Chatterjea, J. N.; Sahai, Radhika P., Journal of the Indian Chemical Society, 1982, vol. 59, # 11/12, p. 1372 - 1374

  摘要：

  DOI：
• 作为产物：
  描述：

  benzothiophene-2,3-dicarboxylic anhydride 在 铜 作用下， 165.0~166.0 ℃ 、2.27 kPa 条件下， 反应 3.5h， 生成 苯并噻吩-3-羧酸甲酯
  参考文献：
  名称：

  Chatterjea, J. N.; Sahai, Radhika P., Journal of the Indian Chemical Society, 1982, vol. 59, # 11/12, p. 1372 - 1374

  摘要：

  DOI：

文献信息

• Transition-Metal-Free Transformation of Aryl Bromides into Aromatic Esters and Amides via Aryl Trichloromethyl Ketones
  作者：Souya Dohi、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1002/ejoc.201301170

  日期：2013.12

  Aryl bromides have been treated with Mg and then chloral, followed by tBuOCl or tBuOCl with I2 as an additive, and subsequently alcohols or amines to form the corresponding aromatic esters and aromatic amides via aryl trichloromethyl ketones as intermediates.

  芳基溴化物先用Mg然后用氯醛处理，然后用t BuOCl或t BuOCl（以I 2为添加剂）处理，然后用醇或胺处理，通过芳基三氯甲基酮作为中间体形成相应的芳族酯和芳族酰胺。
• Synthesis of Novel Highly Active Thiophene and Benzothiophene Containing Diphosphine Ligands and their Use in the Asymmetric Allylation of Catechol
  作者：Lutz F. Tietze、J. Klaas Lohmann、Christian Stadler

  DOI：10.1055/s-2004-822891

  日期：——

  Novel thiophene and benzothiophene containing diphosphine ligands 5-8 with a chiral cyclohexyl diamine backbone have been prepared and used in the asymmetric allylation of catechol. The advantage of these new ligands is their high reactivity and excellent selectivity. The best results were obtained using ligand 7 to give the allylated catechol 24b from 23b in 90% ee and 91% yield within 4 hours.

  新的噻吩和苯并噻吩含有二膦配体 5-8 与手性环己二胺骨架已被制备并用于邻苯二酚的不对称烯丙基化。这些新配体的优点是它们的高反应性和出色的选择性。最好的结果是使用配体 7 在 4 小时内以 90% ee 和 91% 产率从 23b 得到烯丙基化的儿茶酚 24b。
• C2 Arylated Benzo[<i>b</i>]thiophene Derivatives as<i>Staphylococcus aureus</i>NorA Efflux Pump Inhibitors
  作者：François Liger、Pascale Bouhours、Carine Ganem-Elbaz、Claude Jolivalt、Stéphane Pellet-Rostaing、Florence Popowycz、Jean-Marc Paris、Marc Lemaire

  DOI：10.1002/cmdc.201500463

  日期：2016.2

  An innovative and straightforward synthesis of second‐generation 2‐arylbenzo[b]thiophenes as structural analogues of INF55 and the first generation of our laboratory‐made molecules was developed. The synthesis of C2‐arylated benzo[b]thiophene derivatives was achieved through a method involving direct arylation, followed by simple structural modifications. Among the 34 compounds tested, two of them

  开发了一种新颖，直接的合成方法，合成了第二代2-芳基苯并[ b ]噻吩作为INF55的结构类似物，并合成了我们实验室制造的第一代分子。C2芳基化的苯并[ b ]噻吩衍生物的合成是通过涉及直接芳基化，然后进行简单的结构修饰的方法实现的。在测试的34种化合物，其中两人有力诺拉以0.25和0.5微克毫升浓度泵抑制剂，其导致了环丙沙星最小抑制浓度（MIC）的16倍的降低对抗SA-1199B应变-1（1和1.5μ米，分别地）。相对于利血平（MIC = 20μgmL -1），是NorA泵抑制剂中的参考化合物。因此，这些分子代表了与环丙沙星一起用于抗氟喹诺酮耐药菌株的有希望的候选物。
• Piperidine derivatives having anxiolytic effect
  申请人：Lundbeck; H.

  公开号：US05665725A1

  公开（公告）日：1997-09-09

  Piperidine compounds having the general formula (I), ##STR1## wherein R.sup.1 is a group having general formula (II), ##STR2## wherein X is CHR.sup.10, O, S, SO, SO.sub.2 or NR.sup.10, Z.sup.1 is CH.sub.2, O, or S; Z.sup.2 and Z.sup.3 are independently (CH.sub.2).sub.n, n being 0 or 1, O or S or Z.sup.1 and Z.sup.2 may together represent a group --CH.dbd.CH--; or when Z.sup.3 is (CH.sub.2).sub.n wherein n is 0, Z.sup.1 and Z.sup.2 may together represent a 3-membered divalent group; show potent sigma receptor activity. Furthermore they show effect in animal models indicative of anxiolytic properties. Accordingly they are useful as medicines for the treatment of anxiety, psychosis, epilepsy, convulsion, movement disorders, motor disturbances, amnesia, cerebrovascular diseases, senile demential of the Alzheimer type or Parkinson's disease.

  哌啶化合物具有通式（I），其中 R.sup.1 是具有通式（II）的基团，其中 X 是CHR.sup.10，O，S，SO，SO.sub.2或NR.sup.10，Z.sup.1是CH.sub.2，O或S；Z.sup.2和Z.sup.3分别为（CH.sub.2）.sub.n，n为0或1，O或S或Z.sup.1和Z.sup.2可以共同表示一个羟基；或者当Z.sup.3是（CH.sub.2）.sub.n时，其中n为0，Z.sup.1和Z.sup.2可以共同表示一个3-成员双价基团；显示出强大的σ受体活性。此外，它们在动物模型中显示出具有抗焦虑特性的效果。因此，它们可用作治疗焦虑症、精神病、癫痫、抽搐、运动障碍、运动紊乱、健忘症、脑血管疾病、老年性阿尔茨海默病或帕金森病的药物。
• Electrosynthesis of Fluorinated Benzo[b]thiophene Derivatives
  作者：Toshio Fuchigami、Bin Yin、Shinsuke Inagi

  DOI：10.1055/s-0030-1260549

  日期：2011.6

  Anodic fluorination of benzo[b]thiophene derivatives provided a complex mixture of di- and trifluorinated products. On the other hand, anodic fluorination of 3-oxo-2,3-dihydrobenzo[b]thiophene and methyl 3-oxo-2,3-dihydrobenzo[b]thiophene-2-carboxylate gave the corresponding monofluorinated products ­selectively in moderate yields. Anodic fluorination of methyl α-(2-cyanophenylthio)acetate followed by intramolecular cyclization provided 3-amino-2-fluorobenzo[b]thiophene in excellent yield.

  苯并[b]噻吩衍生物的阳极氟化反应产生了一种复杂的二氟和三氟混合物。另一方面，3-氧代-2,3-二氢苯并[b]噻吩和 3-氧代-2,3-二氢苯并[b]噻吩-2-甲酸甲酯的阳极氟化反应以中等产率选择性地得到了相应的单氟化产物。对δ-(2-氰基苯硫基)乙酸甲酯进行阳极氟化，然后进行分子内环化，可以得到产率极高的 3-氨基-2-氟苯并[b]噻吩。