乙基4-羟基-2-(4-甲基苯基)-1,3-噻唑-5-羧酸酯 | 263016-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 乙基4-羟基-2-(4-甲基苯基)-1,3-噻唑-5-羧酸酯
• 英文名称: ethyl 4-hydroxy-2-(4-methylphenyl)-1,3-thiazole-5-carboxylate
• 英文别名: ethyl 4-hydroxy-2-(p-tolyl)thiazole-5-carboxylate
• CAS: 263016-18-8
• 化学式: C₁₃H₁₃NO₃S
• mdl: MFCD00816791
• 分子量: 263.317
• InChiKey: HTQNUGGPEURDFS-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  87.7
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25

SDS

Name:	Ethyl 4-hydroxy-2-(4-methylphenyl)-1 3-thiazole-5-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	263016-18-8

Section 1 - Chemical Product MSDS Name:Ethyl 4-hydroxy-2-(4-methylphenyl)-1 3-thiazole-5-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
263016-18-8	Ethyl 4-hydroxy-2-(4-methylphenyl)-1,3	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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

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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.
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.
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.

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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.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 263016-18-8: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 128 - 130 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: C13H13NO3S
Molecular Weight: 263

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 263016-18-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 4-hydroxy-2-(4-methylphenyl)-1,3-thiazole-5-carboxylate - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 263016-18-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 263016-18-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 263016-18-8 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

反应信息

• 作为反应物：
  描述：

  乙基4-羟基-2-(4-甲基苯基)-1,3-噻唑-5-羧酸酯 、 丙炔酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以67%的产率得到ethyl (E)-4-((3-ethoxy-3-oxoprop-1-en-1-yl)oxy)-2-(p-tolyl)thiazole-5-carboxylate
  参考文献：
  名称：

  新型噻唑支架作为潜在 TRPM8 拮抗剂的设计、合成和生物学评价

  摘要：

  报告了开发一种可行的方法来进一步功能化 4-羟基噻唑衍生物以提供目标 TRPM8 拮抗剂的初步结果。2-(3-氟苯基)-4-三氟甲基磺酰氧基-1,3-噻唑-5-甲酸乙酯的联合Sonogashira偶联/环化反应已应用于合成TRPM8 DFL23448的选择性阻断剂的类似物。在所有合成衍生物中，最有希望的化合物作为 TRPM8 阻滞剂具有活性 (IC50 = 4.06 µM)，显示出优异的代谢稳定性和无细胞毒性作用。最后，衍生物的计算机表征表明没有违反药物相似性规则。

  DOI：

  10.1016/j.bmcl.2021.128392
• 作为产物：
  描述：

  3-甲苯基硫代甲酰胺 、 溴代丙二酸二乙酯 以 乙醇 为溶剂， 反应 0.5h， 以51%的产率得到乙基4-羟基-2-(4-甲基苯基)-1,3-噻唑-5-羧酸酯
  参考文献：
  名称：

  新型噻唑支架作为潜在 TRPM8 拮抗剂的设计、合成和生物学评价

  摘要：

  报告了开发一种可行的方法来进一步功能化 4-羟基噻唑衍生物以提供目标 TRPM8 拮抗剂的初步结果。2-(3-氟苯基)-4-三氟甲基磺酰氧基-1,3-噻唑-5-甲酸乙酯的联合Sonogashira偶联/环化反应已应用于合成TRPM8 DFL23448的选择性阻断剂的类似物。在所有合成衍生物中，最有希望的化合物作为 TRPM8 阻滞剂具有活性 (IC50 = 4.06 µM)，显示出优异的代谢稳定性和无细胞毒性作用。最后，衍生物的计算机表征表明没有违反药物相似性规则。

  DOI：

  10.1016/j.bmcl.2021.128392

文献信息

• Trpm8 antagonists
  申请人：Dompe' S.P.A.

  公开号：EP2606888A1

  公开（公告）日：2013-06-26

  The invention relates to compounds acting as selective antagonists of Transient Receptor Potential cation channel subfamily M member 8 (TRPM8), and having formula: Said compounds are useful in the treatment of diseases associated with activity of TRPM8 such as pain, inflammation, ischaemia, neurodegeneration, stroke, psychiatric disorders, inflammatory conditions and urological disorders.

  该发明涉及作为瞬时受体电位阳离子通道亚家族M成员8（TRPM8）的选择性拮抗剂的化合物，其化学式为：这些化合物在治疗与TRPM8活性相关的疾病方面具有用途，如疼痛、炎症、缺血、神经退行性疾病、中风、精神障碍、炎症性疾病和泌尿系统疾病。
• [EN] TRPM8 ANTAGONISTS<br/>[FR] ANTAGONISTES DE TRPM8
  申请人：DOMPE SPA

  公开号：WO2013092711A1

  公开（公告）日：2013-06-27

  The invention relates to compounds acting as selective antagonists of Transient Receptor Potential cation channel subfamily M member 8 (TRPM8), and having formula (I). Said compounds are useful in the treatment of diseases associated with activity of TRPM8 such as pain, inflammation, ischaemia, neurodegeneration, stroke, psychiatric disorders, itch, irritable bowel diseases, cold induced and/or exhacerbated respiratory disorders and urological disorders.

  该发明涉及作为Transient Receptor Potential阳离子通道亚家族M成员8 (TRPM8)的选择性拮抗剂的化合物，其化学式为(I)。所述化合物在治疗与TRPM8活性相关的疾病方面具有用途，如疼痛、炎症、缺血、神经退行性疾病、中风、精神障碍、瘙痒、肠易激综合征、冷诱导和/或加重的呼吸道疾病以及泌尿系统疾病。
• Discovery of Novel TRPM8 Blockers Suitable for the Treatment of Somatic and Ocular Painful Conditions: A Journey through p<i>K</i>_a and LogD Modulation
  作者：Gianluca Bianchini、Mara Tomassetti、Samuele Lillini、Anna Sirico、Silvia Bovolenta、Lorena Za、Chiara Liberati、Rubina Novelli、Andrea Aramini

  DOI：10.1021/acs.jmedchem.1c01647

  日期：2021.11.25
• TRPM8 ANTAGONISTS
  申请人：Dompe' S.p.A.

  公开号：EP2793883A1

  公开（公告）日：2014-10-29
• US9585875B2
  申请人：——

  公开号：US9585875B2

  公开（公告）日：2017-03-07