2-溴-1-(4-甲基-2-苯基-1,3-噻唑-5-基)-1-乙酮 | 7520-95-8

• 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-溴-1-(4-甲基-2-苯基-1,3-噻唑-5-基)-1-乙酮
• 英文名称: 2-bromo-1-(4-methyl-2-phenylthiazol-5-yl)ethanone
• 英文别名: 2-bromo-1-(4-methyl-2-phenylthiazol-5-yl)ethan-1-one；5-bromoacetyl-4-methyl-2-phenylthiazole；2-bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone；2-bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-ethanone；2-bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)ethanone
• CAS: 7520-95-8
• 化学式: C₁₂H₁₀BrNOS
• 分子量: 296.188
• InChiKey: BOMSILGSXFNLJX-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C
• 沸点：
  409.4±53.0 °C(Predicted)
• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

SDS

Name:	2-Bromo-1-(4-methyl-2-phenyl-1 3-thiazol-5-yl)-ethanone Material Safety Data Sheet
Synonym:	None Known
CAS:	7520-95-8

Section 1 - Chemical Product MSDS Name:2-Bromo-1-(4-methyl-2-phenyl-1 3-thiazol-5-yl)-ethanone Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
7520-95-8	2-Bromo-1-(4-methyl-2-phenyl-1,3-thiaz	95+	unlisted

Hazard Symbols: C
Risk Phrases: 34

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Chronic exposure may cause effects similar to those of acute exposure.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. Wash clothing before reuse.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:

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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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing.
Keep container tightly closed. Do not ingest or inhale. Discard contaminated shoes. Use only with adequate ventilation.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. 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# 7520-95-8: 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: 117-118 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: C12H10BrNOS
Molecular Weight: 296.19

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Alcohols, amines, strong oxidizing agents, bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 7520-95-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-ethanone - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Pseudomonas putida:

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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, ACIDIC, ORGANIC, N.O.S
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE, SOLID, ACIDIC, ORGANIC, N.O.S
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE, SOLID, ACIDIC, ORGANIC, N.O.S
Hazard Class: 8
UN Number: 3261
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 34 Causes burns.
Safety Phrases:
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# 7520-95-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 7520-95-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 7520-95-8 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-甲基-2-苯基-1,3-噻唑-5-基)-1-乙酮 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以85%的产率得到2-azido-1-(4-methyl-2-phenylthiazol-5-yl)ethanone
  参考文献：
  名称：

  新型噻唑基1,2,3-三唑基醇衍生物的合成及抗菌性能评价

  摘要：

  1-（4-甲基-2-芳基-1,3-噻唑-5-基）-2-（4-芳基1,2,3-三唑-1-基）乙醇（6a-t）的新系列）是通过2-叠氮基-1-（4-甲基-2-苯基噻唑-5-基）乙酮（3a-e）与取代的乙炔基苯（4a-c）的点击反应合成，然后用硼氢化钠还原而合成的。筛选了新合成的1-（4-甲基-2-芳基-1,3-噻唑-5-基）-2-（4-芳基1,2,3-三唑-1-基）乙醇衍生物。革兰氏阴性菌株，大肠杆菌（国家工业微生物保藏中心，NCIM 2574），革兰氏阳性菌株白葡萄球菌（NCIM 2178）的体外抗菌活性以及对白色念珠菌（NCIM 3100），黑曲霉的体外抗真菌活性（美国典型培养物保藏中心，ATCC 504），Rhodotorula glutinis（NCIM 3168）和Chensogenum chrysogenum（NCIM 737）。八种噻唑基-1,2,3-三唑基-醇衍生物6a，6i，

  DOI：

  10.1007/s00044-020-02540-5
• 作为产物：
  描述：

  3-溴戊烷-2,4-二酮 以 乙醇 、 二氯甲烷 为溶剂， 反应 14.17h， 生成 2-溴-1-(4-甲基-2-苯基-1,3-噻唑-5-基)-1-乙酮
  参考文献：
  名称：

  4“-甲基-2,2”-二芳基-4,2'：4'，5“-噻唑衍生物的合成，表征和抗菌筛选

  摘要：

  合成了一系列新颖的4“-甲基-2,2”-二芳基-4,2'：4'，5“-叔噻唑（8a-p）衍生物，并筛选了对四种病原细菌，大肠杆菌，假单胞菌荧光，金黄色葡萄球菌和枯草芽孢杆菌。其中，化合物8a和8j表现出优异的抗菌活性，最小抑菌浓度范围为1.0至5.3μg/ mL，化合物8m和8p对所有测试菌株均表现出中等至良好的抗菌活性，最小抑菌浓度范围为16.9至29.7μg/ mL。筛选了所有合成的化合物对念珠菌的体外抗真菌活性。大多数化合物报告中等的抗真菌活性。这项研究为我们正在进行的合理设计更有效的抗菌剂的努力提供了有价值的指导。

  DOI：

  10.1002/jhet.3170

文献信息

• Synthesis and Antimicrobial Evaluation of Some New 4,5′-Bisthiazoles
  作者：Tibor Rozsa、Mihaela Duma、Laurian Vlase、Ioana Ionuţ、Adrian Pîrnău、Brînduşa Tiperciuc、Ovidiu Oniga

  DOI：10.1002/jhet.2054

  日期：2015.7

  bisthiazole derivatives represent a prevalent scaffold in the antimicrobial drug discovery. Therefore, we have decided to synthesize some new series of 4,5′‐bisthiazoles. A total of 17 compounds were synthesized, their structural elucidation being based on elemental analysis (C,H,N,S) and spectroscopic data (MS and 1H NMR). Their in vitro antimicrobial activities were assessed against several Gram‐positive

  噻唑和联噻唑衍生物代表了抗菌药物发现中的普遍支架。因此，我们决定合成一些新的4,5'-双噻唑系列。总共合成了17种化合物，其结构解析基于元素分析（C，H，N，S）和光谱数据（MS和1 H NMR）。使用分光光度法评估了它们对几种革兰氏阳性和革兰氏阴性细菌菌株以及一种真菌菌株（白色念珠菌）的体外抗菌活性。一些化合物对革兰氏阴性大肠杆菌，鼠伤寒沙门氏菌和革兰氏阳性菌表现出中等至良好的抗菌活性。金黄色葡萄球菌和蜡状芽孢杆菌菌株。所有合成的化合物对白念珠菌均具有中度到很好的抑菌活性。
• Dialkylation of Ethyl 4-(Het)aryl-3-oxobutanoates as a Route to 5-(2-Oxoethyl)cyclopentenones
  作者：Andrey G. Lvov、Alexey V. Zakharov、Konstantin A. Lyssenko、Vadim V. Kachala、Valerii Z. Shirinian

  DOI：10.1055/s-0039-1689926

  日期：2019.7

  An unexplored ability of the long-known chemical transformation, Borsche’s cyclopentenone synthesis (the construction of a 1,4-diketone with subsequent base-induced cyclization), is reported. Double alkylation of ethyl 4-(het)aryl-3-oxobutanoates with 2-bromo-1-(het)arylethanones, with subsequent alkali treatment, provides access to cyclopentenones substituted with a 2-oxoethyl group at the 5-position

  报道了一种长期已知的化学转化的未知能力，即 Borsche 的环戊烯酮合成（构建 1,4-二酮和随后的碱诱导环化）。4-（杂）芳基-3-氧代丁酸乙酯与 2-溴-1-（杂）芳基乙酮的双烷基化，随后进行碱处理，提供在 5 位被 2-氧乙基取代的环戊烯酮。这些产物可能作为杂环化的有价值的合成子，并且通过合成 4H-环戊二烯 [b] 噻吩衍生物证明了这一特征。
• 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
• OPIOID RECEPTOR MODULATORS AND USE THEREOF
  申请人：National Health Research Institutes

  公开号：US20170056377A1

  公开（公告）日：2017-03-02

  Disclosed is an in vitro screening method for identifying an antagonist-to-agonist allosteric modifier of a mu-opioid receptor and an in vivo method for confirming that a test compound is such a modifier of a mu-opioid receptor. Also disclosed is a method for treating an opioid receptor-associated condition using a compound of Formula (I) and a pharmaceutical composition containing the same.

  揭示了一种体外筛选方法，用于识别μ-阿片受体的拮抗剂-激动剂异位调节剂，并揭示了一种体内方法，用于确认测试化合物是否为μ-阿片受体的这种调节剂。还揭示了一种使用式（I）化合物和含有该化合物的药物组合物治疗阿片受体相关疾病的方法。
• Novel cyanothiouracil and cyanothiocytosine derivatives as concentration-dependent selective inhibitors of U87MG glioblastomas: Adenosine receptor binding and potent PDE4 inhibition
  作者：Zafer Sahin、Sevde Nur Biltekin、Leyla Yurttas、Barkin Berk、Yağmur Özhan、Hande Sipahi、Zhan-Guo Gao、Kenneth A. Jacobson、Şeref Demirayak

  DOI：10.1016/j.ejmech.2020.113125

  日期：2021.2

  antiviral activity is commonly associated with thiouracil and thiocytosine derivatives, which are well known fragments for adenosine receptor affinity with many associated pharmacological properties. In this respect, 33 novel compounds have been synthesized in two groups: 24 thiouracil derivatives (4a-x) and 9 thiocytosine derivatives (5a-i). Antitumor activity of all the compounds was determined in the

  硫尿嘧啶和硫胞嘧啶是具有药理学多样性的重要杂环药效团。抗肿瘤和抗病毒活性通常与硫氧嘧啶和硫胞嘧啶衍生物相关，它们是众所周知的具有许多相关药理特性的腺苷受体亲和力片段。在这方面，已在两组中合成了 33 种新化合物：24 种硫尿嘧啶衍生物 ( 4a-x ) 和 9 种硫胞嘧啶衍生物 ( 5a-i )。在 U87 MG 胶质母细胞瘤细胞系中测定了所有化合物的抗肿瘤活性。化合物5e显示出抗增殖 IC 50为 1.56 μM，其活性略高于顺铂 (1.67 μM)。11 种最活跃的化合物在 1 μM 时与腺苷 A 1、A 2A或 A 2B受体没有显着结合。脑肿瘤表达大量的磷酸二酯酶。测试了化合物对 PDE4 的抑制作用，5e和5f显示出最佳效力（5e：3.42 μM；5f：0.97 μM）。令人惊讶的是，这些化合物对 U87MG 也是最有效的。然而，这些化合物对 HEK293 健康细胞系缺乏细胞毒性作用，这有助于进一步研究。