4-甲基-2-(3-吡啶)-1,3-噻唑-5-羧酸乙酯 | 39091-00-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-甲基-2-(3-吡啶)-1,3-噻唑-5-羧酸乙酯
• 中文别名: 4-甲基-2-(3-吡啶基)噻唑-5-羧酸乙酯
• 英文名称: ethyl 4-methyl-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate
• 英文别名: 4-methyl-2-(3-pyridyl)thiazole-5-carboxylate ethyl ester；ethyl-4-methyl-2-(pyridin-3-yl)thiazole-5-carboxylate；4-methyl-2-pyridin-3-yl-thiazole-5-carboxylic acid ethyl ester；ethyl 4-methyl-2-(pyridin-3-yl)-5-thiazolecarboxylate；ethyl 4-methyl-2-(3-pyridyl)-5-thiazolecarboxylate；Ethyl 4-methyl-2-pyridin-3-yl-1,3-thiazole-5-carboxylate
• CAS: 39091-00-4
• 化学式: C₁₂H₁₂N₂O₂S
• mdl: MFCD01567252
• 分子量: 248.305
• InChiKey: PNJYSPUXYJWHJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  82-84°
• 沸点：
  396.3±52.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S24/25
• 海关编码：
  2934100090

SDS

Name:	Ethyl 4-methyl-2-pyridin-3-yl-1 3-thiazole-5-carboxylate Material Safety Data Sheet
Synonym:	None Known
CAS:	39091-00-4

Section 1 - Chemical Product MSDS Name:Ethyl 4-methyl-2-pyridin-3-yl-1 3-thiazole-5-carboxylate Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
39091-00-4	Ethyl 4-methyl-2-pyridin-3-yl-1,3-thia	95+	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. May be harmful if absorbed through the skin.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

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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.
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.

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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 appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. 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 cool, dry, well-ventilated area away from incompatible substances.

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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# 39091-00-4: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 56-58 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: C12H12N2O2S
Molecular Weight: 248.3

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 39091-00-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 4-methyl-2-pyridin-3-yl-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
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 22 Do not breathe dust.
S 24/25 Avoid contact with skin and eyes.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 39091-00-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 39091-00-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 39091-00-4 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：

  4-甲基-2-(3-吡啶)-1,3-噻唑-5-羧酸乙酯 在 silica gel 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 9.5h， 生成 2-(4-Methyl-2-pyridin-3-yl-1,3-thiazol-5-yl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  新型带有吡啶基和噻唑基骨架的1,3,4-恶二唑的合成及抗结核活性

  摘要：

  为了寻找更有效和安全的新型抗结核药，此处设计并合成了新的2-吡啶基取代的噻唑基-5-芳基-1,3,4-恶二唑（6a - o），并以亚硫磺酰胺为起始原料，并经过新颖的多步法合成合成路线。当在二氧化硅负载的POCl 3存在下与苯甲酸/烟酸（5a - o）缩合时，中间体吡啶基取代的噻唑基酸酰肼（4）产生更好的标题化合物，收率更高。所有合成的化合物（6a - o）和中间酸酰肼（4）已经筛选了其针对结核分枝杆菌H37Ra（MTB）和牛分枝杆菌BCG的体外抗结核活性。其中，6f，6j，6l和6o在浓度低于3μg/ mL时显示出对牛分枝杆菌BCG的有希望的活性。这些化合物对四种人类癌细胞系显示出低细胞毒性（CC 50：> 100μg/ mL）。还针对分枝杆菌烯酰还原酶（InhA）酶进行了分子对接研究，以深入了解这些分子的结合方式并记录了良好的结合亲和力。还对标题产品的ADME属性进行了分析。

  DOI：

  10.1016/j.bmcl.2016.05.093
• 作为产物：
  描述：

  烟酰胺 在 tetraphosphorus decasulfide 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 11.0h， 生成 4-甲基-2-(3-吡啶)-1,3-噻唑-5-羧酸乙酯
  参考文献：
  名称：

  新型带有吡啶基和噻唑基骨架的1,3,4-恶二唑的合成及抗结核活性

  摘要：

  为了寻找更有效和安全的新型抗结核药，此处设计并合成了新的2-吡啶基取代的噻唑基-5-芳基-1,3,4-恶二唑（6a - o），并以亚硫磺酰胺为起始原料，并经过新颖的多步法合成合成路线。当在二氧化硅负载的POCl 3存在下与苯甲酸/烟酸（5a - o）缩合时，中间体吡啶基取代的噻唑基酸酰肼（4）产生更好的标题化合物，收率更高。所有合成的化合物（6a - o）和中间酸酰肼（4）已经筛选了其针对结核分枝杆菌H37Ra（MTB）和牛分枝杆菌BCG的体外抗结核活性。其中，6f，6j，6l和6o在浓度低于3μg/ mL时显示出对牛分枝杆菌BCG的有希望的活性。这些化合物对四种人类癌细胞系显示出低细胞毒性（CC 50：> 100μg/ mL）。还针对分枝杆菌烯酰还原酶（InhA）酶进行了分子对接研究，以深入了解这些分子的结合方式并记录了良好的结合亲和力。还对标题产品的ADME属性进行了分析。

  DOI：

  10.1016/j.bmcl.2016.05.093

文献信息

• Synthesis and characterizations of novel thiazolyl-thiadiazole derivatives as telomerase activators
  作者：Kayagil, Ismail、Mutlu, Ayşe Gül、Bayhan, Ülkü、Yilmaz, Inanç、Demirayak, Şeref

  DOI：10.3906/kim-1711-92

  日期：——

  Pyridine-3/4-thiocarboxamide derivatives were used as starting materials for the synthesis of the target compounds. The pyridine-3/4-thiocarboxamide derivatives were reacted with ethyl 2-chloroacetoacetate in ethanol to give the thiazole derivatives (1, 2). The two ethyl thiazole-carboxylate derivatives (1, 2) thus obtained were treated with sodium hydroxide solution and ethanol and converted to carboxylic acids (3, 4). The carboxylic acid derivatives (3, 4) were reacted with thiosemicarbazide in phosphoroxy trichloride and aminothiadiazole rings (5, 6) were formed. Thus, two thiazolyl-thiadiazole amine derivatives (5, 6) were obtained. These two derivatives (5, 6) were converted into two chloroacetamidothiadiazole derivatives (7, 8) by reaction with chloroacetylchloride over the amino group in the presence of triethylamine in acetone. After all these steps, the starting materials (7, 8) needed to reach the target compounds were obtained. With the two derivatives (7, 8) obtained in this last step, phenol and thiophenol derivatives were reacted in acetone in the presence of potassium carbonate. The target compounds, thiazolyl-thiadiazole derivatives (TDA$_\mathbf1-16}})$, are completely unique and their structure has been elucidated by elemental analysis, IR, NMR, and MS spectral data. After all these synthesis steps, telomerase activity studies were performed on the target compounds obtained. For this purpose, a PCR ELISA-based TRAP method was used on the heart of zebrafish. According to the enzyme assay results, derivative TDA$_\mathbf8}}$ has shown an increase of telomerase enzyme activity.

  吡啶-3/4-硫代羰胺衍生物被用作合成目标化合物的起始材料。吡啶-3/4-硫代羰胺衍生物与乙基2-氯乙酰乙酸酯在乙醇中反应，得到噻唑衍生物（1，2）。获得的两种乙基噻唑羧酸酯衍生物（1，2）经氢氧化钠溶液和乙醇处理，转化为羧酸（3，4）。羧酸衍生物（3，4）与硫半卡巴脲在磷酰氯中反应，形成氨基噻二唑环（5，6）。因此，得到了两种噻唑基噻二唑胺衍生物（5，6）。这两种衍生物（5，6）通过在醋酮中以三乙胺为存在下的氨基上与氯乙酰氯反应，转化为两种氯乙酰胺基噻二唑衍生物（7，8）。经过所有这些步骤后，得到了达到目标化合物所需的起始材料（7，8）。用最后一步获得的两种衍生物（7，8），在碳酸钾存在下在醋酮中与酚和苯硫酚反应。目标化合物，噻唑基噻二唑衍生物（TDA$_1-16}$），是完全独特的，其结构通过元素分析、红外、核磁共振和质谱数据阐明。经过所有这些合成步骤后，对获得的目标化合物进行了端粒酶活性研究。为此，在斑马鱼心脏上使用了基于PCR ELISA的TRAP方法。根据酶活性测定结果，衍生物TDA$_8}$显示了端粒酶酶活性的增加。
• PYRROLO- AND THIAZOLO-PYRIDINE COMPOUNDS, AND METHODS OF USE THEREOF
  申请人：DENG Shaojiang

  公开号：US20080004309A1

  公开（公告）日：2008-01-03

  The present invention relates to novel compounds capable of modulating the stability and/or activity of hypoxia inducible factor (HIF).

  这项发明涉及一种能够调节缺氧诱导因子（HIF）稳定性和/或活性的新化合物。
• [EN] HERBICIDAL PYRIDINO-/PYRIMIDINO-THIAZOLES<br/>[FR] PYRIDINO/PYRIMIDINO-THIAZOLES HERBICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2016046078A1

  公开（公告）日：2016-03-31

  The present invention relates to herbicidally active pyridino-/pyrimidino-thiazole derivatives, as well as to processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, in crops of useful plants.

  本发明涉及具有除草活性的吡啶基/嘧啶基-噻唑衍生物，以及用于制备这些衍生物的过程和中间体。该发明进一步涉及包含这些衍生物的除草剂组合物，以及在控制不良植物生长方面使用这些化合物和组合物，特别是在有用植物作物中控制杂草的使用。
• 2-吡啶基-4-甲基噻唑-5-甲酸红没药烯酯香 料的生产方法
  申请人：安徽华业香料股份有限公司

  公开号：CN110922398B

  公开（公告）日：2021-02-26

  本发明公开了一种固体酸催化合成2‑吡啶基‑4‑甲基噻唑‑5‑甲酸红没药烯酯香料的生产方法，以烟酰胺为起始物料，与P2S5反应后得到了硫代烟酰胺，硫代烟酰胺与2‑氯乙酰乙酸乙酯进行成环反应得到了2‑吡啶基‑4‑甲基噻唑‑5‑甲酸乙酯，经水解后得到了2‑吡啶基‑4‑甲基噻唑‑5‑甲酸，然后在固体酸催化剂的作用下与红没药醇缩合，经工业柱层析分离，高效率的合成了2‑吡啶基‑4‑甲基噻唑‑5‑甲酸红没药烯酯香料。
• Thiazoles and their use in controlling insects and pests
  申请人：——

  公开号：US04080457A1

  公开（公告）日：1978-03-21

  Certain 2-(3-pyridyl) thiazoles are useful for the control of insects, and are particularly effective against aphids. Many of these thiazoles are new compounds.

  某些2-(3-吡啶基)噻唑化合物对于控制昆虫，特别是蚜虫具有很好的效果，其中许多噻唑化合物是新化合物。