4-(3-溴苯基)噻唑-2-胺 | 105512-81-0

• 物质功能分类: 有机原料 - 杂环化合物
• 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-(3-溴苯基)噻唑-2-胺
• 中文别名: 2-氨基-4-(3-溴苯基)噻唑
• 英文名称: 4-(3-bromophenyl)thiazol-2-amine
• 英文别名: 2-amino-4-(m-bromophenyl)thiazole；4-(3-bromophenyl)-2-aminothiazole；4-(3-Bromophenyl)-1,3-thiazol-2-amine
• CAS: 105512-81-0
• 化学式: C₉H₇BrN₂S
• mdl: MFCD00170238
• 分子量: 255.138
• InChiKey: PDNKBFMOKUBDDR-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131°C
• 沸点：
  398.8±17.0 °C(Predicted)
• 密度：
  1.636

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2934100090
• 危险类别：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H320,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-4-(3-bromophenyl)thiazole
Synonyms: 4-(3-Bromophenyl)thiazol-2-ylamine

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

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-4-(3-bromophenyl)thiazole
CAS number: 105512-81-0

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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.
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.

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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.
Store in closed vessels.
Storage:

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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
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H7BrN2S
Molecular weight: 255.1

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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, hydrogen bromide, 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

制备方法与用途

应用

2-氨基噻唑环类衍生物是杂环化合物中非常重要的一员。其中，2-氨基-4-(3-溴苯基)噻唑可用作医药合成中间体。该结构在农药和医药领域中有广泛应用，许多具有抗炎、抗肿瘤、抗病毒及镇静作用的天然产物或小分子药物含有此结构单元，是近年来绿色药物研究中最常构建的官能团之一。

制备

2-氨基-4-(3-溴苯基)噻唑的制备方法如下：在25 mL反应瓶中依次加入3 mL水、30 μL环糊精、0.50 mmol 1-溴-3-乙苯、1.50 mmol NBS和0.05 mmol AIBN，于60℃下反应4小时。反应结束后冷却，再依次加入1.50 mmol 碳酸氢钠和0.50 mmol 硫脲，在80℃下继续反应1小时。反应结束后，加入乙酸乙酯并用饱和食盐水萃取有机相，浓缩后通过柱层析得到97 mg白色固体2-氨基-4-(3-溴苯基)噻唑，收率为76%。

反应信息

• 作为反应物：
  描述：

  4-(3-溴苯基)噻唑-2-胺 在 亚硝酸异戊酯 作用下， 以 四氢呋喃 为溶剂， 120.0 ℃ 、700.01 kPa 条件下， 反应 0.33h， 以51%的产率得到4-(3-bromophenyl)thiazole
  参考文献：
  名称：

  芳香杂环的流动加氢重氮

  摘要：

  连续流动加工用于用氢化物快速取代芳族氨基。该方法应用于一系列芳香杂环，证实了该过程的广泛范围和取代基耐受性。使用流动设备并优化工艺以克服在先前依赖批处理程序的研究中限制产率的有问题的不稳定中间体。研究了各种常见的有机溶剂作为潜在的氢化物来源。该方法允许使用纯有机可溶系统以良好的产率对关键结构（例如氨基吡唑和氨基吡啶）进行脱氨基。

  DOI：

  10.3390/molecules24101996
• 作为产物：
  描述：

  3-溴苯乙烯 在 1,3-二溴-5,5-二甲基海因 、 水 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 4-(3-溴苯基)噻唑-2-胺
  参考文献：
  名称：

  由1,3-二溴-5,5-二甲基乙内酰脲（DBH）介导的苯乙烯衍生物合成2-氨基噻唑

  摘要：

  据报道，通过DBH介导的苯乙烯和硫脲的氧化环化合成2-氨基噻唑的有效方法。使用DBH作为溴源和氧化剂，通过两步一锅法成功地将各种烯烃成功转化为相应的2-氨基噻唑，产率为10-81％。该方法可以容易地以克为单位进行，并且成功地用于以苯乙烯为起始原料的抗炎药fanetizole的合成。

  DOI：

  10.1016/j.tet.2018.05.021

文献信息

• Inhibitors of histone deacetylase
  申请人：——

  公开号：US20020177594A1

  公开（公告）日：2002-11-28

  Compounds having the formula 1 or therapeutically acceptable salts thereof, are histone deacetylase (HDAC) inhibitors. Preparation of the compounds, compositions containing the compounds, and treatment of diseases using the compounds are disclosed.

  具有以下化学式的化合物或其治疗上可接受的盐是组蛋白去乙酰化酶（HDAC）抑制剂。本文揭示了该化合物的制备、含有该化合物的组合物以及使用该化合物治疗疾病的方法。
• [EN] 2-ACYLAMINOTHIAZOLES FOR THE TREATMENT OF CANCER<br/>[FR] 2-ACYLAMINOTHIAZOLES POUR LE TRAITEMENT DU CANCER
  申请人：UNIV MILANO BICOCCA

  公开号：WO2015001024A1

  公开（公告）日：2015-01-08

  The present invention relates to inhibitors of the oncogenic protein kinase ALK of formula (I) as herein described and pharmaceutical compositions thereof. The compounds of formula (I) are useful in the preparation of a medicament, in particular for the treatment of cancer.

  本发明涉及如下所述的化学式(I)的致癌蛋白激酶ALK的抑制剂及其药物组合物。化学式(I)的化合物在制备药物方面是有用的，特别是用于癌症治疗。
• Solid state thiazole-based fluorophores: Promising materials for white organic light emitting devices
  作者：Kumar Godugu、Sultana Shaik、Mohammad Khaja Mohinuddin Pinjari、Trivikram Reddy Gundala、Dwaraka Viswanath Chellappa Subramanyam、Subramanyam Sarma Loka、Haranath Divi、Vemula Venkatramu、Chinna Gangi Reddy Nallagondu

  DOI：10.1016/j.dyepig.2020.109077

  日期：2021.3

  solid state white light emissive thiazole-based donor-acceptor (D-A) type fluorophores, 2-(3-pyridyl)/2-aminothiazoles from ω-bromomethylketones and pyridine-3-carbothioamide/thiourea in the presence of silica-supported HClO4 as a reusable solid Brønsted acid catalyst at RT. The photophysical and electrochemical properties of these compounds have been derived. Most of the studied D-A type solid thiazole-based

  已开发出一种简便且更有效的无溶剂机械化学合成路线，用于合成一系列固态白光发射的噻唑基供体-受体（DA）型荧光团，2-（3-吡啶基）/ 2-氨基噻唑在室温下，作为可重复使用的固体布朗斯台德酸催化剂，在二氧化硅负载的HClO 4存在下，ω-溴甲基酮和吡啶-3-碳硫酰胺/硫脲。已经推导了这些化合物的光物理和电化学性质。大多数研究过的DA型基于噻唑的固体荧光团都发出白光，并且可以通过在第4个引入各种取代基从温暖的（理想的）冷的白光进行调谐。2-（3-吡啶基）/ 2-氨基噻唑的位置。此外，发现标题化合物的HOMO和LUMO能级分别在-5.52eV至-5.72eV和-1.84eV至-2.45eV的范围内。这些水平的噻唑基荧光团的寿命已通过发光衰减曲线确定，发现范围为7.7–11μs。合成的噻唑基荧光团的光物理和电化学性质表明，该化合物可能是用于白色有机发光器件的有前途的材料。
• Citric Acid-catalyzed Synthesis of 2,4-Disubstituted Thiazoles from Ketones via C-Br, C-S, and C-N Bond Formations in One Pot: A Green Approach
  作者：Trivikram Reddy Gundala、Kumar Godugu、Chinna Gangi Reddy Nallagondu

  DOI：10.1002/jccs.201700200

  日期：2017.12

  protocol has been developed for the synthesis of 2,4‐disubstituted thiazoles via C–Br, C–S, and, C–N bond formations in a single step from readily available ketones, N‐bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α‐bromoketones, ease of carrying

  已开发出一种改进的，更环保的方案，可通过一步一步从现成的酮类N-溴代琥珀酰亚胺（NBS），C-Br，C-S和C-N键的形成中合成2,4-二取代的噻唑，在回流条件下，柠檬酸在乙醇和水（3：1）的混合物中由柠檬酸催化硫脲。该方法的优点是无需分离催泪性α-溴代酮，易于操作，反应曲线更干净，底物范围宽，无需色谱纯化和适合大规模合成。
• Pyridine and pyrimidine derivatives as mGIuR2 antagonists
  申请人：McArthur Silvia Gatti

  公开号：US20070232583A1

  公开（公告）日：2007-10-04

  The present invention relates to compounds of formula (I), a process for the manufacture thereof, pharmaceutical compositions containing them, and their use for treating CNS disorders: wherein A, B, X, Y, R 1 , R 2 , R 3 and R 4 are as defined in the description and claims.

  本发明涉及式(I)的化合物，其制造方法，含有它们的药物组合物，以及它们用于治疗中枢神经系统疾病的用途：其中A、B、X、Y、R1、R2、R3和R4如描述和权利要求中所定义。