4-甲基-2-噻吩硼酸 | 162607-15-0

• 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 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 4-甲基-2-噻吩硼酸
• 中文别名: 4-甲基噻吩-2-硼酸；2-硼酸-4-甲基噻吩
• 英文名称: (4-methyl-2-thienyl)boronic acid
• 英文别名: 4-methylthiophen-2-ylboronic acid；4-methylthiophene-2-boronic acid；(4-methylthiophen-2-yl)boronic acid
• CAS: 162607-15-0
• 化学式: C₅H₇BO₂S
• mdl: MFCD01319040
• 分子量: 141.986
• InChiKey: DFUMIZDUIJNUJU-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  305.4±44.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT, KEEP COLD
• 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
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存放于0至6℃阴凉干燥处

SDS

Name:	4-Methylthiophene-2-boronic acid Material Safety Data Sheet
Synonym:	4-Methyl-2-thienylboric acid
CAS:	162607-15-0

Section 1 - Chemical Product MSDS Name:4-Methylthiophene-2-boronic acid Material Safety Data Sheet
Synonym:4-Methyl-2-thienylboric acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
162607-15-0	4-Methylthiophene-2-boronic acid	100	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. Do NOT use mouth-to-mouth resuscitation.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4C/39F.)

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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# 162607-15-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Not available.
Odor: Not available.
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: C5H7BO2S
Molecular Weight: 141.97

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, light, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents, acids, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide, boron oxides.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 162607-15-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Methylthiophene-2-boronic acid - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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# 162607-15-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 162607-15-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 162607-15-0 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

4-甲基噻吩-2-硼酸是一种噻吩衍生物，广泛应用于合成农药、医药、化学试剂、染料和高分子助剂等。

制备

将3.0g（8.85mmol）七水合磷酸钾、1.50g（5.90mmol）联硼酸频哪醇酯B2(pin)2、12mg（0.015mmol）Xphos-Pd-G2和4mg（0.008mmol）Xphos依次加入反应瓶中，加入6mL乙醇搅拌均匀，再加入0.36mL（2.95mmol）4-甲基噻吩-2-氯代物。在室温下反应1小时后，向反应液中加入5mL乙酸乙酯稀释，并经硅藻土过滤、乙酸乙酯洗涤，合并滤液减压浓缩得到粗产物。然后通过硅胶柱层析分离，使用石油醚-乙酸乙酯洗脱，最终获得4-甲基噻吩-2-硼酸频哪醇酯。

接着将4-甲基噻吩-2-硼酸频哪醇酯加入反应瓶中，并滴加稀HCl进行水解。溶液先产生沉淀，随着沉淀逐渐消失，调节体系pH值至1。向溶液中滴加质量分数为25％的NaOH溶液，直至pH值达到13，搅拌1小时后分液。有机相用15mL的质量分数为10％的NaOH萃取两次，将水相合并，并用15mLTHF分别萃取碱液两次。调pH值使溶液开始产生浑浊，慢慢出现絮状物，最终将pH值调整至5.0。最后使用70mL THF萃取水相，有机相旋干、提纯后得到4-甲基噻吩-2-硼酸。

反应信息

• 作为反应物：
  描述：

  4-甲基-2-噻吩硼酸 在 四(三苯基膦)钯 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 6-(3-methylthiophen-5-yl)-9-(β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides

  摘要：

  Significant anti-HCV activity of 6-hetarylpurine ribonucleosides has been discovered and is reported here for the first time and compared with cytostatic effect. An extended series of 6-hetarylpurine ribonucleosides has been prepared by heterocyclizations in position 6 of purine nucleosides or by cross-couplings of 6-chloropurine nucleosides with hetarylboronic acids, -stannanes, or -zinc halides. The most anti-HCV active were purine ribonucleosides bearing pyrrol-3-yl (3k) or 2-furyl (3g) groups exerting EC90 = 0.14 and 0.4 mu M, respectively.

  DOI：

  10.1021/jm050335x
• 作为产物：
  描述：

  2-溴-4-甲基噻吩 在 盐酸 、 仲丁基锂 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.08h， 生成 4-甲基-2-噻吩硼酸
  参考文献：
  名称：

  一种单杂环硼酸的制备方法

  摘要：

  本发明提供了一种单杂环硼酸的制备方法，所述制备方法包括以下步骤：(1)将式I所示化合物与烷基硼酸酯溶于溶剂A中，得到A溶液，将有机锂试剂溶于溶剂B中，得到B溶液，将A溶液与B溶液连续加料反应，流出反应管后终止反应得到中间体；(2)将步骤(1)得到的中间体经水解反应后得到所述单杂环硼酸；本发明所提供的制备方法能够提高反应收率，最高可达到95％以上，减少反应时间，可在5‑60min中内完成反应，并且可以使反应温度提高，降低了低温反应的能耗，温度可控，安全性提高，压力控制方便，自动化程度提高，有利于生产操作，成本降低，提升经济效益。

  公开号：

  CN108440587A

文献信息

• [EN] AURORA KINASE MODULATORS AND METHOD OF USE<br/>[FR] MODULATEURS D'AURORA KINASE ET PROCÉDÉ D'UTILISATION
  申请人：AMGEN INC

  公开号：WO2009117157A1

  公开（公告）日：2009-09-24

  The present invention relates to chemical compounds having a general formula (I) wherein A1-5 and 7-8, D', L1, L2, R1, R3, R6-8, n and o are defined herein, and synthetic intermediates, which are capable of modulating the activity of Aurora kinase proteins and, thereby, influencing various disease states and conditions related to the activities of Aurora kinases. For example, the compounds are capable of influencing the process of cell cycle and cell proliferation to treat cancer and cancer-related diseases. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of Aurora kinase.

  本发明涉及具有一般式(I)的化合物，其中在此定义了A1-5和7-8，D'，L1，L2，R1，R3，R6-8，n和o，以及合成中间体，这些化合物能够调节枢纽激酶蛋白的活性，从而影响与枢纽激酶活动相关的各种疾病状态和病况。例如，这些化合物能够影响细胞周期和细胞增殖过程，以治疗癌症和与癌症相关的疾病。该发明还包括包括这些化合物的药物组合物，以及治疗与枢纽激酶活性相关的疾病状态的方法。
• [EN] METHODS OF TREATMENT OF AMYLOIDOSIS USING ASPARTYL-PROTEASE INIHIBITORS<br/>[FR] PROCEDES DE TRAITEMENT D'AMYLOIDOSE UTILISANT DES INHIBITEURS DE PROTEASE ASPARTYLE
  申请人：ELAN PHARM INC

  公开号：WO2005070407A1

  公开（公告）日：2005-08-04

  The invention relates to acetyl 2-hydroxy-1,3-diaminospirocyclohexanes and derivatives thereof that are useful in treating diseases, disorders, and conditions associated with amyloidosis. Amyloidosis refers to a collection of diseases, disorders, and conditions associated with abnormal deposition of A-beta protein.

  这项发明涉及乙酰2-羟基-1,3-二氨基螺环己烷及其衍生物，可用于治疗与淀粉样变性相关的疾病、疾病和症状。淀粉样变性是指与A-beta蛋白异常沉积相关的一系列疾病、疾病和症状。
• [EN] PIPERAZINE DERIVATIVES USEFUL FOR THE TREATMENT OF GASTROINTESTINAL DISORDERS<br/>[FR] DERIVES DE PIPERAZINE CONVENANT POUR LE TRAITEMENT DE TROUBLES GASTRO-INTESTINAUX
  申请人：GLAXO GROUP LTD

  公开号：WO2006010629A1

  公开（公告）日：2006-02-02

  The invention provides compounds of formula (I) or pharmaceutically acceptable salts thereof, wherein Ra, Rb, Rc, Rd, Re, Rf and Y are as defined in the specification. The compounds are partial or full agonists at the growth hormone secretagogue (GHS) receptors . Pharmaceutical compositions comprising the compounds, methods of preparing the compounds, uses of the compounds and methods involving the compounds are also provided.

  这项发明提供了式（I）的化合物或其药用盐，其中Ra、Rb、Rc、Rd、Re、Rf和Y如规范中所定义。这些化合物是生长激素分泌素（GHS）受体的部分或全激动剂。还提供了包括这些化合物的药物组合物、制备这些化合物的方法、这些化合物的用途以及涉及这些化合物的方法。
• Aurora Kinase Modulators and Method of Use
  申请人：Amgen Inc.

  公开号：US20140336182A1

  公开（公告）日：2014-11-13

  The present invention relates to chemical compounds having a general formula I wherein A 1-8 , D′, L 1 , L 2 , R 1 , R 6-8 and n are defined herein, and synthetic intermediates, which are capable of modulating various protein kinase receptor enzymes and, thereby, influencing various disease states and conditions related to the activities of such kinases. For example, the compounds are capable of modulating Aurora kinase thereby influencing the process of cell cycle and cell proliferation to treat cancer and cancer-related diseases. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of Aurora kinase.

  本发明涉及具有一般式I的化合物，其中A1-8、D'、L1、L2、R1、R6-8和n在此处定义，并且具有调节各种蛋白激酶受体酶并因此影响与这些激酶活动相关的各种疾病状态和病况的能力的合成中间体。例如，这些化合物能够调节枢纽激酶，从而影响细胞周期和细胞增殖过程，以治疗癌症和与癌症相关的疾病。该发明还包括包括这些化合物的药物组合物，以及治疗与枢纽激酶活性相关的疾病状态的方法。
• [EN] CRYSTALLINE FORMS OF N-(4-((3-(2-AMINO-4-PYRIMIDINYL) - 2-PYRIDINYL)OXY)PHENYL)-4-(4-METHYL-2-THIENYL)-1 -PHTHALAZINAMINE PHARMACEUTICALLY ACCEPTABLE SALTS AND USES THEREOF<br/>[FR] FORMES CRISTALLINES DE SELS PHARMACEUTIQUEMENT ACCEPTABLES DE LA N-(4-((3-(2-AMINO-4-PYRIMIDINYL)-2-PYRIDINYL)OXY)PHÉNYL)-4-(4-MÉTHYL-2-THIÉNYL)-1-PHTALAZINAMINE ET LEURS UTILISATIONS
  申请人：AMGEN INC

  公开号：WO2015084649A1

  公开（公告）日：2015-06-11

  The present invention relates to crystalline forms and co-crystal forms of pharmaceutically acceptable salts of the compound, N-(4-((3-(2-amino-4-pyrimidinyl)-2-pyridinyl)oxy)phenyl)-4-(4-methyl-2-thienyl)-1-phthalazinamine (AMG 900, and pharmaceutical compositions comprising said crystalline and co-crystal forms thereof. The invention further provides uses of the crystalline foms and compositions, to treat cancer, including various types of solid tumors and hematologic cancer including myeloma and leukemia.

  本发明涉及药用可接受盐的晶型和共晶型形式，该盐为化合物N-(4-((3-(2-氨基-4-嘧啶基)-2-吡啶基)氧基)苯基)-4-(4-甲基-2-噻吩基)-1-鞣酸苄胺（AMG 900），以及包括所述晶型和共晶型形式的药物组合物。该发明还提供了利用这些晶型和组合物治疗癌症的用途，包括各种固体肿瘤和血液癌症，包括骨髓瘤和白血病。