2-溴-1-[4-(2-噻吩基)苯基]-1-乙酮 | 128746-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-1-[4-(2-噻吩基)苯基]-1-乙酮
• 中文别名: 2-溴-1-[4-(2-噻吩)苯基]-1-乙酮
• 英文名称: 2-bromo-1-[4-(2-thienyl)phenyl]-1-ethanone
• 英文别名: 2-(4-bromoacetylphenyl)thiophene；2-bromo-1-(4-thiophen-2-ylphenyl)ethanone
• CAS: 128746-80-5
• 化学式: C₁₂H₉BrOS
• 分子量: 281.173
• InChiKey: QFHKNYPNLSJEQI-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  367.6±22.0 °C(Predicted)
• 密度：
  1.488±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  T,C
• 海关编码：
  2934999090

SDS

Name:	2-Bromo-1-[4-(2-thienyl)phenyl]-1-ethanone Material Safety Data Sheet
Synonym:
CAS:	128746-80-5

Section 1 - Chemical Product MSDS Name:2-Bromo-1-[4-(2-thienyl)phenyl]-1-ethanone Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
128746-80-5	2-Bromo-1-[4-(2-thienyl)phenyl]-1-etha	97+%	unlisted

Hazard Symbols: C
Risk Phrases: 20/21/22 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed. Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Harmful if absorbed through the skin. Causes skin burns.
Ingestion:
Harmful if swallowed. Causes gastrointestinal tract burns.
Inhalation:
Harmful if inhaled. Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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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 immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 foam, dry chemical, or carbon dioxide.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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# 128746-80-5: 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: Off white
Odor: Without to slight
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 115 - 117 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: C12H9BrOS
Molecular Weight: 281.17

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 128746-80-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Bromo-1-[4-(2-thienyl)phenyl]-1-ethanone - 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
Shipping Name: CORROSIVE SOLID, TOXIC, N.O.S.*
Hazard Class: 8 (6.1)
UN Number: 2923
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, TOXIC, N.O.S.
Hazard Class: 8 (6.1)
UN Number: 2923
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, TOXIC, N.O.S.
Hazard Class: 8 (6.1)
UN Number: 2923
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 34 Causes burns.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 128746-80-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 128746-80-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 128746-80-5 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：

  2-溴-1-[4-(2-噻吩基)苯基]-1-乙酮 在 sodium tetrahydroborate 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.5h， 生成 N-(4-fluorobenzyl)-3,4-dimethoxy-N-((4-(4-(thiophen-2-yl)phenyl)thiazol-2-yl)methyl)aniline
  参考文献：
  名称：

  作为胆固醇酯转移抑制剂的 N,N-二取代-4-芳基噻唑-2-甲胺衍生物的设计、合成和生物学评价

  摘要：

  胆固醇酯转移蛋白 (CETP) 因其在反向胆固醇转移 (RCT) 过程中的重要作用而被确定为心血管疾病 (CVD) 的潜在靶标。在我们之前的工作中，化合物 5 被发现是一种温和的 CETP 抑制剂。利用构象限制策略设计了用杂环芳烃取代酰胺接头，然后设计了一系列 N,N-取代-4-芳基噻唑-2-甲胺衍生物。合成了 36 种化合物并评估了它们的 CETP 抑制活性。构效关系研究表明，电子供体基团取代了环 A，环 B 的 4 位上的吸电子基团对效力至关重要。在这些化合物中，化合物30表现出优异的CETP抑制活性（IC50=0.79±0。

  DOI：

  10.3390/molecules22111925
• 作为产物：
  描述：

  1-(4-噻吩-2-苯基)-乙酮 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以33%的产率得到2-bromo-5-(4-bromoacetylphenyl)thiophene
  参考文献：
  名称：

  具有抗氧化剂和角鲨烯合酶抑制活性的降脂（杂）芳族四氢-1,4-恶嗪衍生物。

  摘要：

  发现许多新合成的2- [4-（杂）芳基]苯基-2-羟基-四氢-1,4-恶嗪衍生物和大鼠角鲨烯均抑制脂质过氧化（最有效的IC50为20 microM）。合酶（IC50多数在1-10 microM之间）。在体内已证明了抗血脂异常的作用：最有效的化合物以56 micromol / kg（ip）的剂量将高脂血症大鼠的甘油三酸酯，总胆固醇和LDL-胆固醇分别降低了64％，67％和82％。大多数新型化合物比结构上相关的和参考的联苯吗啉具有更高的活性，这为抗动脉粥样硬化剂的设计提供了有用的结构方法。

  DOI：

  10.1021/jm800663w

文献信息

• Synthesis and structure–activity relationship of aminoarylthiazole derivatives as correctors of the chloride transport defect in cystic fibrosis
  作者：Emanuela Pesce、Marta Bellotti、Nara Liessi、Sara Guariento、Gianluca Damonte、Elena Cichero、Andrea Galatini、Annalisa Salis、Ambra Gianotti、Nicoletta Pedemonte、Olga Zegarra-Moran、Paola Fossa、Luis J.V. Galietta、Enrico Millo

  DOI：10.1016/j.ejmech.2015.05.030

  日期：2015.6

  targeted by small molecules called generically correctors and potentiators, respectively. Aminoarylthiazoles (AATs) represent an interesting class of compounds that includes molecules with dual activity, as correctors and potentiators. With the aim to improve the activity profile of AATs, we have now designed and synthesized a library of novel compounds in order to establish an initial SAR that may provide

  囊性纤维化跨膜电导调节剂 (CFTR) 是存在于上皮细胞膜中的氯离子通道。影响CFTR的突变基因导致囊性纤维化（CF），一种多器官严重疾病。最常见的 CF 突变 F508del 会损害 CFTR 蛋白的加工和活性（门控）。其他突变，如 G551D，只会导致门控缺陷。加工和门控缺陷可以分别被称为一般校正剂和增强剂的小分子作为目标。氨基芳基噻唑 (AAT) 代表了一类有趣的化合物，包括具有双重活性的分子，作为校正剂和增强剂。为了改善 AAT 的活性特征，我们现在设计并合成了一个新化合物库，以建立一个初始 SAR，该 SAR 可以提供有关对救援活动有益或有害的化学基团的指示。使用功能测定法在表达 CFBE41o 的 F508del-CFTR 中测试了新化合物作为校正剂和增强剂。双重活性化合物 AAT-如图 4a 所示，当与校正剂 VX-809 组合时，其特征在于提高的功效和显着的协同作用。此外，通过计算方法，已检测到核苷酸结合域
• <scp>Electrooxidation‐Induced</scp> C(sp ³ )–H/C(sp ² )–H <scp>Radical‐Radical Cross‐Coupling</scp> between Xanthanes and <scp>Electron‐Rich</scp> Arenes
  作者：Yuwei Liang、Linbin Niu、Xing‐An Liang、Shengchun Wang、Pengjie Wang、Aiwen Lei

  DOI：10.1002/cjoc.202200020

  日期：2022.6.15

  bonds has been a priority research topic in organic synthesis. Minsici reactions have been the powerful methods for C(sp3) − C(sp2) bonds formation. Despite its mature development, the scopes of arenes are usually suitable for electron-deficient heterocyclic compounds, rather than electron-rich arenes. Herein, we report an electrooxidation-induced alkylation of electron-rich arenes with H2 evolution

  C(sp 3 ) - H 键的芳基化一直是有机合成的重点研究课题。Minsici 反应是 C(sp 3 ) - C(sp 2 ) 键形成的有力方法。尽管发展成熟，但芳烃的范围通常适用于缺电子杂环化合物，而不是富电子芳烃。在此，我们报道了在无外源氧化剂的条件下，富电子芳烃的电氧化诱导烷基化并释放出 H 2，避免了金属催化剂的使用。该协议适用于各种富电子苯胺衍生物和含氮杂环化合物。我们预计这种电氧化 C(sp 3) - H 芳基化代表了经典芳烃烷基化的重要扩展，从而为自由基交叉偶联化学的发展提供了一种有吸引力的策略。
• IMIDAZO[1,2-A]PYRIDINE DERIVATIVES AS MODULATORS OF THE 5-HT2A SEROTONIN RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO
  申请人：Xiong Yifeng

  公开号：US20110263592A1

  公开（公告）日：2011-10-27

  Imidazo[1,2-α]pyridine derivatives of Formula (Ia) and pharmaceutical compositions thereof that modulate the activity of the 5-HT 2A serotonin receptor. Compounds and pharmaceutical compositions thereof are directed to methods useful in the treatment of insomnia, dyssomnia, parasomnia and related sleep disorders, platelet aggregation, coronary artery disease, myocardial infarction, transient ischemic attack, angina, stroke, atrial fibrillation, thrombosis, asthma or symptoms thereof, agitation or symptoms thereof, behavioral disorders, drug induced psychosis, excitative psychosis, Gilles de Ia Tourette's syndrome, manic disorder, organic or NOS psychosis, psychotic disorders, psychosis, acute schizophrenia, chronic schizophrenia, NOS schizophrenia and related disorders, diabetic-related disorders, progressive multifocal leukoencephalopathy and the like. The present invention also relates to methods for the treatment of 5-HT 2A serotonin receptor mediated disorders in combination with other pharmaceutical agents administered separately or together.

  公式（Ia）的咪唑[1,2-α]吡啶衍生物及其制药组合物，可调节5-HT2A 5-羟色胺受体的活性。该化合物及其制药组合物适用于治疗失眠、睡眠障碍、血小板聚集、冠状动脉疾病、心肌梗死、短暂性脑缺血发作、心绞痛、中风、心房颤动、血栓形成、哮喘或其症状、烦躁或其症状、行为障碍、药物诱导的精神病、兴奋性精神病、Gilles de Ia Tourette综合症、躁狂障碍、器质性或NOS精神病、精神病性障碍、急性精神分裂症、慢性精神分裂症、NOS精神分裂症及相关疾病、糖尿病相关疾病、进行性多灶性白质脑病等治疗方法。本发明还涉及与其他药物分别或联合使用治疗5-HT2A 5-羟色胺受体介导的疾病的方法。
• Imidazo[1,2-α]pyridine derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto
  申请人：Arena Pharmaceuticals, Inc.

  公开号：US10058549B2

  公开（公告）日：2018-08-28

  rmidazo[1,2-α]pyridine derivatives of Formula (Ia) and pharmaceutical compositions thereof that modulate the activity of the 5-HT2A serotonin receptor. Compounds and pharmaceutical compositions thereof are directed to methods useful in the treatment of insomnia, dyssomnia, parasomnia and related sleep disorders, platelet aggregation, coronary artery disease, myocardial infarction, transient ischemic attack, angina, stroke, atrial fibrillation, thrombosis, asthma or symptoms thereof, agitation or symptoms thereof, behavioral disorders, drug induced psychosis, excitative psychosis, Gilles de Ia Tourette's syndrome, manic disorder, organic or NOS psychosis, psychotic disorders, psychosis, acute schizophrenia, chronic schizophrenia, NOS schizophrenia and related disorders, diabetic- related disorders, progressive multifocal leukoencephalopathy and the like. The present invention also relates to methods for the treatment of 5-HT2A serotonin receptor mediated disorders in combination with other pharmaceutical agents administered separately or together.

  式（Ia）的咪唑并[1,2-α]吡啶衍生物及其药物组合物，可调节 5-HT2A 血清素受体的活性。其化合物和药物组合物用于治疗失眠、失眠症、副失眠和相关睡眠障碍、血小板聚集、冠状动脉疾病、心肌梗塞、短暂性脑缺血发作、心绞痛、中风、心房颤动、血栓形成、哮喘或其症状、躁动或其症状、行为障碍、药物性精神病、兴奋性精神病、Gilles de Ia Tourette 综合征、躁狂症、器质性或非器质性精神病、精神障碍、精神病、急性精神分裂症、慢性精神分裂症、非器质性精神分裂症及相关疾病、糖尿病相关疾病、进行性多灶性白质脑病等。本发明还涉及与其他药剂单独或联合给药治疗 5-HT2A 血清素受体介导的疾病的方法。
• Discovery of novel VX-809 hybrid derivatives as F508del-CFTR correctors by molecular modeling, chemical synthesis and biological assays
  作者：Alice Parodi、Giada Righetti、Emanuela Pesce、Annalisa Salis、Bruno Tasso、Chiara Urbinati、Valeria Tomati、Gianluca Damonte、Marco Rusnati、Nicoletta Pedemonte、Elena Cichero、Enrico Millo

  DOI：10.1016/j.ejmech.2020.112833

  日期：2020.12

  Cystic fibrosis (CF) is the autosomal recessive disorder most recurrent in Caucasian populations. It is caused by different mutations in the cystic fibrosis transmembrane regulator protein (CFTR) gene, with F508del being the most common. During the last years, small-molecule therapy chosen to contrast CF relied on compounds that correct CFTR misfolding and ER retention (correctors such as VX-809), or defective channel gating (potentiators such as VX-770). Combination therapy with the two series of drugs has been applied, leading to the approval of several multi-drugs such as Orkambi. Despite this, this treatment proved to be only partially effective making the search for novel modulators an urgent need to contrast CF. Recently, we reported compound 2a as reference compound of a series of aminoarylthiazole-VX-809 hybrid derivatives exhibiting promising F508del-CFTR corrector ability. Herein, we report exploring the docking mode of the prototype VX-809 and of 2a in order to derive useful guidelines for the rational design of novel optimized analogues. To demonstrate experimentally their effective F508del-CFTR-binding and rescuing potential, the most promising derivatives had been synthesized and evaluated in biological assays including YFP functional assay on F508del-CFTR CFBE41o-cells, trans epithelial electrical resistance (TEER) and surface plasmon resonance (SPR). This multidisciplinary strategy led to the discovery of a second series of hybrids including 7j and 7m endowed with higher potency than the prototype.