5-溴乙酰水杨酰胺 | 73866-23-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酰亚胺
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-溴乙酰水杨酰胺
• 中文别名: 5-溴乙酰基-2-羟基苯酰胺
• 英文名称: 5-(2-bromoacetyl)-2-hydroxybenzamide
• 英文别名: 5-(bromoacetyl)-salicylamide；5-(bromoacetyl)-2-hydroxybenzamide；3-carbamoyl-4-hydroxy-α-bromoacetophenone；5-(Bromoacetyl)salicylamide
• CAS: 73866-23-6
• 化学式: C₉H₈BrNO₃
• mdl: MFCD00792456
• 分子量: 258.071
• InChiKey: VXWSXLSUWGZOHD-UHFFFAOYSA-N

物化性质

• 熔点：
  200-210°C
• 沸点：
  420.2±40.0 °C(Predicted)
• 密度：
  1.705±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：

  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2924299090
• RTECS号：
  CV2365900
• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存放在密封容器内，并置于阴凉、干燥处。请务必远离氧化剂。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromoacetyl salicylamide
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Bromoacetyl salicylamide
CAS number: 73866-23-6

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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.
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.
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
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H8BrNO3
Molecular weight: 258.1

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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.

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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

用途
这是一种重要的医药中间体，广泛应用于柳胺心定等药物的制造。
此外，它还主要用于克霉唑的中间体以及邻氯苯甲酰氯的生产。

反应信息

• 作为反应物：
  描述：

  5-溴乙酰水杨酰胺 以 水 、 二甲基亚砜 、 异丙醇 为溶剂， 以92%的产率得到5-(Dihydroxyacetyl)-2-hydroxybenzamide
  参考文献：
  名称：

  Process for preparing albuterol, acetal, hemi-acetal, and hydrates of

  摘要：

  本文介绍了芳基乙醇胺，尤其是沙丁胺醇（albuterol或salbutamol），以及它们的新颖硼，缩醛和半缩醛中间体的制备方法。

  公开号：

  US05283359A1
• 作为产物：
  描述：

  5-乙酰基水杨酰胺 在 phenyltrimethylammonium tribromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以29%的产率得到5-溴乙酰水杨酰胺
  参考文献：
  名称：

  p-Hydroxyphenacyl photoremovable protecting groups — Robust photochemistry despite substituent diversity

  摘要：

  一项关于各种取代基对对羟基苯乙酯光化学重排影响的广泛研究表明，常见取代基（如 F、MeO、CN、CO2R、CONH2 和 CH3）对光-Favorskii 重排和酸离去基团释放的速率和量子效率影响很小，对反应三重态的寿命影响也很小。当光解在缓冲水介质中进行时，pH 值超过发色团的基态 pKao（其中共轭碱是主要形式），则释放和重排的量子产率在所有取代基中都会降低。否则，取代基对这些坚固发色团的光反应影响很小。

  DOI：

  10.1139/v10-143

文献信息

• Arylethanolamines derived from salicylamide with .alpha.- and .beta.-adrenoceptor blocking activities. Preparation of labetalol, its enantiomers and related salicylamides
  作者：James E. Clifton、Ian Collins、Peter Hallett、David Hartley、Lawrence H. C. Lunts、Philip D. Wicks

  DOI：10.1021/jm00348a013

  日期：1982.6

  A series of phenethanolamines (3) based on salicylamide has been prepared and shown to possess beta-adrenergic blocking properties. When the basic nitrogen atom was substituted by some aralkyl groups, the compounds also blocked alpha-adrenoceptors. The 1-methyl-3-phenylpropyl derivative labetalol (34) is antihypertensive in animals and man, and syntheses of its four stereoisomers are described. The

  已经制备了一系列基于水杨酰胺的苯乙醇胺（3），并显示出具有β-肾上腺素阻断特性。当碱性氮原子被某些芳烷基取代时，这些化合物也会封闭α-肾上腺素受体。1-甲基-3-苯基丙基衍生物拉贝洛尔（34）在动物和人类中均具有降压作用，并描述了其四种立体异构体的合成。在两个不对称中心具有R构型的对映体90具有大部分的β-阻断活性，但是几乎没有α-阻断活性。在醇碳上具有S构型并且在氨基取代基上具有R构型的化合物主要是α-肾上腺素受体阻断剂89。
• The Effect of Some 4,2 and 5,2 Bisthiazole Derivatives on Nitro-Oxidative Stress and Phagocytosis in Acute Experimental Inflammation
  作者：Cătălin Araniciu、Alina Pârvu、Mariana Palage、Smaranda Oniga、Daniela Benedec、Ilioara Oniga、Ovidiu Oniga

  DOI：10.3390/molecules19079240

  日期：——

  Nineteen bisthiazoles were tested in order to assess their anti-inflammatory and antioxidant properties. First, we evaluated the in vitro direct antioxidant capacity of the bisthiazoles using the DPPH radical scavenging method. Then, the anti-inflammatory effect was tested in acute rat experimental inflammation by measuring the acute phase bone marrow response, the phagocytic capacity and the serum nitro-oxidative stress status. Although none of the substances showed significant direct antioxidant potential in the DPPH assay, most of them improved serum oxidative status, when administered to rats with inflammation. Four of the bisthiazoles proved to have good anti-inflammatory properties, similar or superior to that of equal doses meloxicam.

  测试了19种双硫杂环烷以评估其抗炎和抗氧化特性。首先，我们使用DPPH自由基清除法评估了双硫杂环烷的体外直接抗氧化能力。然后，通过测量急性期骨髓反应、吞噬能力和血清氮-氧化应激状态，在急性大鼠实验性炎症中测试了其抗炎效果。尽管在DPPH实验中没有任何物质显示出明显的直接抗氧化潜力，但在给予患有炎症的大鼠时，大多数双硫杂环烷改善了血清氧化状态。其中四种双硫杂环烷显示出良好的抗炎特性，与同等剂量的美洛昔康相似或更优。
• Design and Synthesis of Novel 1,3-Thiazole and 2-Hydrazinyl-1,3-Thiazole Derivatives as Anti-Candida Agents: In Vitro Antifungal Screening, Molecular Docking Study, and Spectroscopic Investigation of their Binding Interaction with Bovine Serum Albumin
  作者：Andreea-Iulia Pricopie、Ioana Ionuț、Gabriel Marc、Anca-Maria Arseniu、Laurian Vlase、Adriana Grozav、Luiza Ioana Găină、Dan C. Vodnar、Adrian Pîrnău、Brîndușa Tiperciuc、Ovidiu Oniga

  DOI：10.3390/molecules24193435

  日期：——

  with the reference drug fluconazole (15.62 μg/mL). Their anti-Candida activity is also supported by molecular docking studies, using the fungal lanosterol C14α-demethylase as the target enzyme. The interaction of the most biologically active synthesized compound 7e with bovine serum albumin was investigated through fluorescence spectroscopy, and the obtained data suggested that this molecule might efficiently

  在用于治疗念珠菌属感染的临床批准药物数量有限的背景下，随着现有抗真菌药物耐药性的迅速发展，两个新系列的4-苯基-1,3-噻唑和合成了 2-肼基-4-苯基-1,3-噻唑衍生物并在体外测试了其抗念珠菌潜力。两种化合物（7a 和 7e）对致病性白色念珠菌菌株表现出良好的抑制活性，与参比药物氟康唑（15.62 μg/mL）相比，其 MIC 值（分别为 7.81 μg/mL 和 3.9 μg/mL）显着降低。 。它们的抗念珠菌活性也得到了分子对接研究的支持，使用真菌羊毛甾醇 C14α-去甲基酶作为目标酶。通过荧光光谱研究了最具生物活性的合成化合物7e与牛血清白蛋白的相互作用，获得的数据表明该分子可以在体内有效地结合载体蛋白以到达靶位点。
• Synthesis and antimicrobial activity of some new N-(aryl-oxo-alkyl)-5-arylidene-thiazolidine-2,4-diones
  作者：Anca Stana、Brînduşa Tiperciuc、Mihaela Duma、Adrian Pîrnău、Philippe Verité、Ovidiu Oniga

  DOI：10.2298/jsc130114078s

  日期：——

  A series of new 5-(2,6-dichlorobenzylidene)thiazolidine-2,4-dione and 5-(4-methoxy-benzylidene)thiazolidine-2,4-dione derivatives (3a-h and 5a-h) were synthesized starting from 5-arylidene-thiazolidine-2,4-dione and ?-halo-ketones. The structural elucidation of the newly synthesized compounds was based on elemental analysis and spectroscopic data (MS, 1H-NMR, 13C-NMR). The synthesized compounds were screened for their antimicrobial activities against several pathogenic strains of Gram-positive and Gram-negative bacteria and one fungal strain (Candida albicans), assessed in vitro as growth inhibition diameters. Some of them displayed better inhibitory activities than that of the reference drug against the Gram-positive S. aureus, B. cereus, L. monocytogenes bacterial strains, and showed good antifungal activity against C. albicans, while the antibacterial activity against Gram-negative E. coli and S. typhimurium bacterial strains was moderate.

  一系列新的 5-(2,6-二氯亚苄基)噻唑烷-2,4-二酮和 5-(4-甲氧基-亚苄基)噻唑烷-2,4-二酮衍生物（3a-h 和 5a-h） 和 5-(4-甲氧基-亚苄基)噻唑烷-2,4-二酮衍生物（3a-h 和 5a-h 卤酮。新合成化合物的结构阐释基于元素分析和光谱分析。 基于元素分析和光谱数据（质谱、1H-NMR、13C-NMR）。 对合成的化合物进行了抗菌活性筛选 的抗菌活性进行了筛选。 细菌和一种真菌菌株（白色念珠菌）的抗菌活性进行了筛选。 生长抑制直径。其中一些药物对革兰氏阳性菌、革兰氏阴性菌和一种真菌菌株（白色念珠菌）的抑制 对革兰氏阳性金黄色葡萄球菌、蜡样芽孢杆菌和白色念珠菌的抑制活性优于参照药物。 金黄色葡萄球菌、蜡样芽孢杆菌和单核细胞增多性酵母菌菌株的抑制活性优于参考药物，并对白色念珠菌表现出良好的抗真菌活性。 对白癣菌的抗真菌活性，而对革兰氏阴性大肠杆菌的抗菌活性 对革兰氏阴性大肠杆菌和伤寒杆菌菌株的抗菌活性为 中度。
• New 2-Phenylthiazoles as Potential Sortase A Inhibitors: Synthesis, Biological Evaluation and Molecular Docking
  作者：Smaranda Oniga、Cătălin Araniciu、Mariana Palage、Marcela Popa、Mariana-Carmen Chifiriuc、Gabriel Marc、Adrian Pirnau、Cristina Stoica、Ioannis Lagoudis、Theodoros Dragoumis、Ovidiu Oniga

  DOI：10.3390/molecules22111827

  日期：——

  inhibitors provided the starting point for identifying a new potential scaffold. Based on this template a series of new potential Sortase A inhibitors, that contain the 2-phenylthiazole moiety, were synthesized. The physicochemical characterisation confirmed the identity of the proposed structures. Antibacterial activity evaluation showed that the new compounds have a reduced activity against bacterial

  Sortase A 抑制是通过影响控制生物膜形成、宿主细胞进入、免疫反应的逃避和抑制以及必需营养素获取的许多关键过程来降低细菌毒力的成熟策略。对已知充当分选酶 A 抑制剂的结构的荟萃分析为识别新的潜在支架提供了起点。基于该模板，合成了一系列新的潜在分选酶 A 抑制剂，其中包含 2-苯基噻唑部分。物理化学表征证实了所提出结构的身份。抗菌活性评估表明，新化合物对细菌细胞活力的活性降低。然而，这些化合物在非常低的浓度下可防止生物膜形成，尤其是在粪肠球菌的情况下。