2-氨基-4-苯基噻唑-5-羧酸甲酯 | 893652-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-氨基-4-苯基噻唑-5-羧酸甲酯
• 英文名称: methyl 2-amino-4-phenylthiazole-5-carboxylate
• 英文别名: methyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate
• CAS: 893652-36-3
• 化学式: C₁₁H₁₀N₂O₂S
• 分子量: 234.279
• InChiKey: CEMUUPHRYZQKGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934100090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Methyl 2-amino-4-phenylthiazole-5-carboxylate
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: Methyl 2-amino-4-phenylthiazole-5-carboxylate
CAS number: 893652-36-3

---

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.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
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.

---

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.

---

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.

---

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.
Store in closed vessels.
Storage:

---

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.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H10N2O2S
Molecular weight: 234.3

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氨基-4-苯基噻唑-5-羧酸甲酯 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.25h， 生成 2-([1,1'-biphenyl]-4-carboxamido)-4-phenylthiazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis of thiazolyl-based hydroxamic acids as histone deacetylase inhibitors

  摘要：

  DOI：

  10.24820/ark.5550190.p011.279
• 作为产物：
  描述：

  methyl (Z)-3-amino-3-phenylacrylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 2-氨基-4-苯基噻唑-5-羧酸甲酯
  参考文献：
  名称：

  由烯胺酮，KSCN和NBS进行溶剂控制的硫氰酸化烯胺酮和2-氨基噻唑的合成。

  摘要：

  已经从烯胺酮，硫氰酸钾和N-溴代琥珀酰亚胺证明了有效且简单的溶剂控制的硫氰酸酯化的烯胺酮和2-氨基噻唑的合成。该方法的特点是反应条件温和，操作简便，反应时间短，收率和化学选择性高，从而为简单地改变溶剂控制的硫氰酸化的烯胺酮和取代的2-氨基噻唑的发散合成提供了有效的方法。所有反应组分都是可商购的或以低成本容易获得的。这些方法在有机化学和药物化学应用中的潜在实用性得到了强调。

  DOI：

  10.1021/acs.joc.9b01722

文献信息

• TBHP/AIBN-Mediated Synthesis of 2-Amino-thioazoles from Active Methylene Ketones and Thiourea under Metal-free Conditions
  作者：Jiyun Sun、Huaibin Ge、Xiaohua Zhen、Xuechan An、Guangtao Zhang、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1016/j.tet.2018.02.064

  日期：2018.4

  A new oxidative system of tert-butyl hydroperoxide (TBHP)/azodiisobutyronitrile (AIBN) has been used for the first time for a convenient, metal-free synthesis of substituted 2-aminothioazoles from active methylene ketone derivatives and thiourea. The reaction is postulated to proceed via an oxidative cyclization initiated by a radical process and followed by a condensation reaction.

  首次使用叔丁基过氧化氢（TBHP）/偶氮二异丁腈（AIBN）的新氧化系统，从活性亚甲基酮衍生物和硫脲方便，无金属地合成取代的2-氨基噻唑。假定该反应通过自由基过程引发的氧化环化进行，然后进行缩合反应。
• 一种合成2-氨基噻唑衍生物的方法
  申请人：天津大学

  公开号：CN107739350B

  公开（公告）日：2020-12-22

  本发明公开了一种合成2‑氨基噻唑衍生物的方法，步骤为：以α位带有吸电子取代基的酮类衍生物(I)与硫脲(II)为原料，以过氧叔丁醇为氧化剂，偶氮二异丁腈为自由基引发剂，在室温～回流的条件下，在溶剂甲醇中发生自由基偶联反应及脱水反应，生成2‑氨基噻唑衍生物(III)；反应式为：本发明利用非金属的偶氮二异丁腈和过氧叔丁醇的自由基氧化体系，避免了昂贵的过渡金属催化剂的使用，拓宽了底物的范围，使用羰基α位是吸电子取代基的底物即可，易离去基团不再是必须的。具有操作简单，反应原料以及反应试剂易得，收率较高等优点。
• Metal-Free Synthesis of Thiocyanated Aminonitroalkenes and 2-Aminothiazoles/selenazoles from β-Aminonitroalkenes and N‑Thio/Selenocyanatosaccharin
  作者：Zhong Li、Hongchen Yang、Yuce Chen、Xiaoyong Xu

  DOI：10.1055/a-1929-2515

  日期：2023.1

  has been developed for the synthesis of thiocyanated aminonitroalkenes and 2,4,5-trisubstituted thiazoles/selenazoles from β-aminonitroalkenes and N‑thio/selenocyanatosaccharin. This method features simple operation, mild reaction conditions, short reaction time, good functional group compatibility and metal-free characteristics. The broad applications of polysubstituted thiazoles/selenazoles in organic

  开发了一种方便有效的方案，用于从 β-氨基硝基烯烃和 N-硫代/硒代氰酸糖精合成硫氰化氨基硝基烯烃和 2,4,5-三取代噻唑/硒唑。该方法具有操作简单、反应条件温和、反应时间短、官能团相容性好、无金属等特点。多取代噻唑/硒唑在有机和药物化学中的广泛应用使该协议更加实用。
• Discovery of novel N-(5-(arylcarbonyl)thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl)amides as potent RORγt inhibitors
  作者：Yonghui Wang、Wei Cai、Guifeng Zhang、Ting Yang、Qian Liu、Yaobang Cheng、Ling Zhou、Yingli Ma、Ziqiang Cheng、Sijie Lu、Yong-Gang Zhao、Wei Zhang、Zhijun Xiang、Shuai Wang、Liuqing Yang、Qianqian Wu、Lisa A. Orband-Miller、Yan Xu、Jing Zhang、Ruina Gao、Melanie Huxdorf、Jia-Ning Xiang、Zhong Zhong、John D. Elliott、Stewart Leung、Xichen Lin

  DOI：10.1016/j.bmc.2013.12.021

  日期：2014.1

  Novel series of N-(5-(arylcarbonyl) thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl) amides were discovered as potent retinoic acid receptor-related orphan receptor-gamma-t (ROR gamma t) inhibitors. SAR studies of the ROR gamma t HTS hit 6a led to identification of thiazole ketone amide 8h and thiophene ketone amide 9g with high binding affinity and inhibitory activity of Th17 cell differentiation. Compound 8h showed in vivo efficacy in both mouse experimental autoimmune encephalomyelitis (EAE) and collagen induced arthritis (CIA) models via oral administration. (C) 2013 Elsevier Ltd. All rights reserved.
• PREPARATION AND METHODS OF USE FOR ORTHO-ARYL 5-MEMBERED HETEROARYL-CARBOXAMIDE CONTAINING MULTI-TARGETED KINASE INHIBITORS
  申请人：Spacefill Enterprises LLC

  公开号：US20180125848A1

  公开（公告）日：2018-05-10

  The present disclosure relates to compounds of the Formula (I): and pharmaceutically acceptable salts, as kinase modulators, compatible with the Type-II inhibition of kinases.