3-羟基苯并[B]噻吩-2-羧酸甲酯 | 13134-76-4

• 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 - 苯并噻吩类
• 中文名称: 3-羟基苯并[B]噻吩-2-羧酸甲酯
• 英文名称: methyl 3-hydroxybenzo[b]thiophene-2-carboxylate
• 英文别名: methyl 3-hydroxy-1-benzothiophene-2-carboxylate
• CAS: 13134-76-4
• 化学式: C₁₀H₈O₃S
• mdl: MFCD00067732
• 分子量: 208.238
• InChiKey: KNSQDHMBDAMMNO-UHFFFAOYSA-N

物化性质

• 熔点：
  106-108°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 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：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 安全说明：
  S26,S36/37/39
• 储存条件：
  2-8℃，惰性气体

SDS

Name:	Methyl 3-hydroxybenzo[b]thiophene-2-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	13134-76-4

Section 1 - Chemical Product MSDS Name:Methyl 3-hydroxybenzo[b]thiophene-2-carboxylate 97% Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13134-76-4	Methyl 3-hydroxybenzo[b]thiophene-2-ca	97%	236-066-4

Hazard Symbols: XI
Risk Phrases: 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

---

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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

---

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.

---

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.

---

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.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 13134-76-4: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 106 - 108 deg C
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: C10H8O3S
Molecular Weight: 208

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, bases.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13134-76-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 3-hydroxybenzo[b]thiophene-2-carboxylate - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 13134-76-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13134-76-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13134-76-4 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-羟基苯并[B]噻吩-2-羧酸甲酯 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以65%的产率得到3-hydroxy-benzo[b]thiophene-2-carboxylic acid
  参考文献：
  名称：

  Efficient synthesis and 5-LOX/COX-inhibitory activity of some 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives

  摘要：

  A series of 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives has been prepared and subsequently evaluated with regards to the inhibition of 5-LOX/COX. Structure optimization furnished derivatives with promising in vitro activity as dual 5-LOX/COX inhibitors with submicromolar IC50 values for inhibition of 5-LOX and COX-1, respectively. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.012
• 作为产物：
  描述：

  2-thiocyanatobenzoic acid 在 盐酸 、 sodium sulfide 、 sodium hydroxide 作用下， 生成 3-羟基苯并[B]噻吩-2-羧酸甲酯
  参考文献：
  名称：

  Friedlaender, Chemische Berichte, 1906, vol. 39, p. 1062

  摘要：

  DOI：

文献信息

• As many as six tandem reactions in one step! Unprecedented formation of highly functionalized benzothiophenes
  作者：Pushparathinam Gopinath、Surapaneni Nilaya、Tripathy Ranjan Debi、Venkatachalam Ramkumar、Kannoth Manheri Muraleedharan

  DOI：10.1039/b914424b

  日期：——

  A novel reaction pathway involving 1,3-diketones and 2,2′-dithiodibenzoylchloride that gives access to benzothiophenes with spiroketal, lactone, carbonyl, hydroxyl and carboxylic acid functionalities is discussed.

  讨论了一种涉及1,3-二酮和2,2′-二硫代二苯甲酰氯的新颖反应途径，该途径可用于合成具有螺环缩酮、内酯、羰基、羟基和羧酸功能的苯并噻吩。
• [EN] 5-MEMBERED AND BICYCLIC HETEROCYCLIC AMIDES AS INHIBITORS OF ROCK<br/>[FR] AMIDES HÉTÉROCYCLIQUES À 5 CHAÎNONS ET BICYCLIQUES UTILISÉS EN TANT QU'INHIBITEURS DE ROCK
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2019014308A1

  公开（公告）日：2019-01-17

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically-acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供了化合物的结构式（I）：或其立体异构体、互变异构体或药学上可接受的盐，其中所有变量如本文所定义。这些化合物是选择性ROCK抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用它们治疗心血管、平滑肌、肿瘤学、神经病理学、自身免疫、纤维化和/或炎症性疾病的方法。
• 一种腙类化合物及其中间体，及其制备方法、药物组合物和应用
  申请人：中国科学院上海有机化学研究所

  公开号：CN110092784A

  公开（公告）日：2019-08-06

  本发明公开了一种腙类衍生物(I)、其中间体、制备方法、药物组合物和应用。本发明的腙类化合物对cIAP1蛋白的泛素化活性具有很好的抑制作用，并在细胞水平促进致癌蛋白c‑MYC的降解，抑制肿瘤细胞的生长，具有广阔的药物开发前景。
• Synthesis and properties of a benzo[1,2-b:4,5-b′]dithiophene core π-system that bears alkyl, alkylthio and alkoxy groups at 3,7-positions
  作者：Shinya Ota、Sojiro Minami、Koji Hirano、Tetsuya Satoh、Yutaka Ie、Shu Seki、Yoshio Aso、Masahiro Miura

  DOI：10.1039/c3ra41822g

  日期：——

  A synthetic sequence was developed to provide 3,7-didodecylbenzo[1,2-b:4,5-b′]dithiophene and its dialkylthio and dialkoxy analogues as planar and soluble building-blocks for constructing benzodithiophene-based π-systems. The benzodithiophenes were also transformed to the corresponding 2,6-di(5-phenyl-2-thienyl)-capped derivatives as the representative oligomers. Their absorption and emission spectra as well as CV data showed that the HOMO–LUMO energy gaps of the dialkylthio and dialkoxy derivatives are smaller than that of the dialkyl one, which is attributable to the lower ELUMO as well as EHOMO energies of the dialkylthio analogue and the higher EHOMO energy of the dialkoxy analogue, respectively. The intra- and intermolecular charge-carrier mobilities were then estimated by the flash-photolysis time-resolved microwave conductivity (FP-TRMC) method and solution-processed top contact FET performance. The TRMC method showed similar high intrinsic hole mobilities (0.16–0.24 cm2 V−1 s−1) irrespective of the substituents, whereas the dialkyl derivative especially displayed a good field-effect mobility of 0.023 cm2 V−1 s−1.

  开发了一种合成序列，提供3,7-二十二烷基苯并[1,2-b:4,5-b']二噻吩及其二烷硫基和二烷氧基类似物，作为构建苯并二噻吩基π系统的平面和可溶性构建块。苯并二噻吩也被转化为相应的2,6-二(5-苯基-2-噻吩基)封端衍生物作为代表性寡聚物。它们的吸收和发射光谱以及CV数据显示，二烷硫基和二烷氧基衍生物的HOMO-LUMO能隙小于二烷基衍生物，这可归因于二烷硫基类似物的较低ELUMO和EHOMO能量，以及二烷氧基类似物的较高EHOMO能量。然后通过闪光光解时间分辨微波电导(FP-TRMC)方法和溶液处理顶部接触FET性能估算了分子内和分子间的载流子迁移率。TRMC方法显示，无论取代基如何，固有空穴迁移率相似且高(0.16-0.24 cm² V⁻¹ s⁻¹)，而二烷基衍生物尤其显示出良好的场效应迁移率0.023 cm² V⁻¹ s⁻¹。
• 3-Alkoxy-thianapthene-2-carboxamides
  申请人：Societe d'Etudes Scientifiques et Industrielles de l'Ile-de-France

  公开号：US03954748A1

  公开（公告）日：1976-05-04

  The 3-alkoxy-thianaphthene-2-carboxamides of this invention are effective for the treatment of mammals afflicted with emesis. When administered to dogs in dosages of 250 .mu.g/kg, compounds of this invention give 100% protection against vomiting normally induced by subcutaneous administration of apomorphine. The compounds of this invention also favorably modify behavior disturbances in mammals.

  这项发明的3-烷氧基噻吩并2-羧酰胺对患有呕吐症的哺乳动物有效。当以250微克/千克的剂量给狗服用时，这项发明的化合物可使狗免受皮下注射阿波莫啡引起的呕吐，保护效果达到100%。这项发明的化合物还有助于改善哺乳动物的行为紊乱。