4-噻唑甲酸乙酯 | 14527-43-6

• 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 - 唑类
• 中文名称: 4-噻唑甲酸乙酯
• 中文别名: 噻唑-4-羧酸乙酯；噻唑-4-甲酸乙酯；4-噻唑羧酸乙酯
• 英文名称: ethyl thiazole-4-carboxylate
• 英文别名: 4-ethoxycarbonyl thiazole；ethyl 1,3-thiazole-4-carboxylate
• CAS: 14527-43-6
• 化学式: C₆H₇NO₂S
• mdl: MFCD25975110
• 分子量: 157.193
• InChiKey: XDOKFEJMEJKVGX-UHFFFAOYSA-N

物化性质

• 熔点：
  42-44
• 沸点：
  130°C 12mm
• 密度：
  1.242±0.06 g/cm3(Predicted)
• 闪点：
  >110℃
• 溶解度：
  可溶于氯仿、二氯甲烷、乙醚、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2934100090
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件：2-8°C，密闭干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl thiazole-4-carboxylate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: Ethyl thiazole-4-carboxylate
CAS number: 14527-43-6

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H7NO2S
Molecular weight: 157.2

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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, nitrogen oxides, 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：

  4-噻唑甲酸乙酯 在 sodium hydroxide 作用下， 生成 噻唑-4-羧酸
  参考文献：
  名称：

  Discovery of N‐(phenylsulfonyl)thiazole‐2‐carboxamides as potent α‐glucosidase inhibitors

  摘要：

  摘要 为寻找治疗糖尿病的新型非糖α-葡萄糖苷酶抑制剂，设计并合成了一系列 N-（苯磺酰基）噻唑-2-甲酰胺衍生物，然后对其α-葡萄糖苷酶抑制活性进行了评估。发现了几个具有良好α-葡萄糖苷酶抑制作用的化合物。其中，化合物 W24 显示出较低的细胞毒性和良好的 α-葡萄糖苷酶抑制活性，其 IC50 值为 53.0 ± 7.7 μM，与市售药物阿卡波糖（IC50 = 228.3 ± 9.2 μM）相比更具竞争力。W24 被确定为开发α-葡萄糖苷酶抑制剂的一个有希望的候选化合物。为了揭示活性化合物与α-葡萄糖苷酶的结合模式，还进行了分子对接研究和分子动力学模拟，结果表明最佳化合物 W24 的结合自由能为 36.3403 ± 3.91 kcal/mol。

  DOI：

  10.1002/ddr.22128
• 作为产物：
  描述：

  2-溴噻唑-4-甲酸乙酯 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以88%的产率得到4-噻唑甲酸乙酯
  参考文献：
  名称：

  新法呢基蛋白转移酶抑制剂的设计，合成和药理评估。

  摘要：

  新的CA（1）A（2）X拟肽被描述为法呢基转移酶抑制剂（FTIs）。它们包括半胱氨酸和蛋氨酸，作为法呢基化蛋白质C端序列的模拟物。此外，考虑到锌的作用和氨基酸的代谢不稳定性，半胱氨酸被杂环取代。8在酶的活性位点上的分子对接以及该化合物的药理学评价说明了一类新的FTI。

  DOI：

  10.1021/jm010297r

文献信息

• 2-Thioethenyl substituted carbapenem derivatives
  申请人：Maruyama Takahisa

  公开号：US20070004700A1

  公开（公告）日：2007-01-04

  [Objective] An objective of the present invention is to provide compounds that are effective against various resistant bacteria which cause current clinical problems, for example, pneumococci including penicillin resistant Streptococcus pneumoneae (PRSP), Haemophilus influenzae including bata-lactamase-nonproducing ampicillin-resistant Haemophilus influenzae (BLNAR), and Moraxella ( Branhamella ) catarrhalis. [Structure] The present invention provides 2-ethenylthio-based carbapenem derivatives represented by the formula (I) or pharmaceutically acceptable salts thereof that are effective, for example, against pneumococci including penicillin resistant Streptococcus pneumoneae (PRSP), Haemophilus influenzae including beta-lactamase-nonproducing ampicillin-resistant Haemophilus influenzae (BLNAR), and Moraxella (Branhamella) catarrhalis:

  本发明的一个目标是提供对抗引起当前临床问题的各种耐药细菌有效的化合物，例如对抗青霉素耐药的肺炎球菌（PRSP）、包括产β-内酰胺酶非产生性氨苄青霉素耐药的流感嗜血杆菌（BLNAR）和喜马拉雅链球菌（布兰氏链球菌）等。本发明提供了以公式（I）表示的基于2-乙烯硫的碳青霉烯衍生物或其药用可接受盐，例如对抗青霉素耐药的肺炎球菌（PRSP）、包括产β-内酰胺酶非产生性氨苄青霉素耐药的流感嗜血杆菌（BLNAR）和喜马拉雅链球菌（布兰氏链球菌）有效。
• Practical, metal-free remote heteroarylation of amides <i>via</i> unactivated C(sp³)–H bond functionalization
  作者：Nana Tang、Xinxin Wu、Chen Zhu

  DOI：10.1039/c9sc02564b

  日期：——

  heteroarylation of amides via C(sp3)–H bond functionalization. Amidyl radicals are directly generated from the amide N–H bonds under mild conditions, which trigger the subsequent 1,5-HAT process. A wide scope of aliphatic amides including carboxamides, sulfonamides, and phosphoramides are readily modified at remote C(sp3)–H bonds by installing diverse heteroaryl groups. Borne out of pragmatic consideration

  开发用于生产多功能酰胺的实用方法是合成化学和药物发现中最重要的主题之一。本文公开了一种通过C（sp 3）–H键功能化实现的酰胺的新型高效位点选择性杂芳基化反应。酰胺基自由基是在温和条件下直接从酰胺N–H键生成的，从而引发随后的1,5-HAT过程。通过安装各种杂芳基，很容易在远处的C（sp 3）–H键处修饰各种脂肪族酰胺，包括羧酰胺，磺酰胺和磷酰胺。出于务实的考虑，该协议可用于酰胺的后期功能化。
• An Improved Synthesis of Pyridine−Thiazole Cores of Thiopeptide Antibiotics
  作者：Virender S. Aulakh、Marco A. Ciufolini

  DOI：10.1021/jo900950x

  日期：2009.8.7

  oxidation of 2-methylthiazoles to 2-formylthiazoles simplifies the implementation of the Bagley variant of the Bohlmann−Rahtz reaction as a key step in a concise new route to pyridine cores of thiopeptide antibiotics.

  将2-甲基噻唑氧化为2-甲酰基噻唑简化了Bohlmann-Rahtz反应的Bagley变体的实施，这是在简化的硫肽抗生素吡啶核新途径中的关键步骤。
• Acetamide and substituted acetamide-containing thiourea inhibitors of herpes viruses
  申请人：American Home Products Corporation

  公开号：US06335350B1

  公开（公告）日：2002-01-01

  Compounds of the formula: are useful in the treatment of diseases associated with herpes viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses-6 and -7, and Kaposi herpesvirus.

  该式化合物在治疗与疱疹病毒相关的疾病中很有用，包括人类巨细胞病毒、单纯疱疹病毒、EB病毒、水痘-带状疱疹病毒、人类疱疹病毒6和7，以及卡波西氏疱疹病毒。
• Diaminopuridine-containing thiourea inhibitors of herpes viruses
  申请人：American Home Products Corporation

  公开号：US06166028A1

  公开（公告）日：2000-12-26

  Compounds of the formula ##STR1## are useful in the treatment of diseases associated with herpes viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses-6 and -7, and Kaposi herpesvirus.

  式为##STR1##的化合物在治疗与疱疹病毒相关的疾病中很有用，包括人类巨细胞病毒、单纯疱疹病毒、EB病毒、水痘-带状疱疹病毒、人类疱疹病毒-6和-7，以及卡波西氏疱疹病毒。