4-[(4-溴苄基)氧基]苯甲醛 | 149833-95-4

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-[(4-溴苄基)氧基]苯甲醛
• 中文别名: 4-(4-溴苄氧基)苯甲醛
• 英文名称: 4-(4-bromobenzyloxy)benzaldehyde
• 英文别名: 4-[(4-bromophenyl)methoxy]benzaldehyde
• CAS: 149833-95-4
• 化学式: C₁₄H₁₁BrO₂
• mdl: MFCD02091001
• 分子量: 291.144
• InChiKey: HGCGRPJQAXHMMI-UHFFFAOYSA-N

物化性质

• 熔点：
  88-92 °C (lit.)
• 沸点：
  419.3±25.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• WGK Germany：
  3
• 海关编码：
  2913000090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332
• 储存条件：
  密封储存，宜存放在阴凉、干燥的仓库中。为了防止与空气反应，通常需要使用惰性气体进行保护。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-(4-Bromobenzyloxy)benzaldehyde
CAS-No. : 149833-95-4

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C14H11BrO2
Molecular Weight : 291,14 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Hydrogen bromide gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Handle and store under inert gas. Air sensitive.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 88 - 92 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
and is applicable to the product with regard to appropriate safety precautions. It does not represent any

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-[(4-溴苄基)氧基]苯甲醛 在 哌啶 、 吡啶 、 氯化亚砜 作用下， 反应 4.4h， 生成
  参考文献：
  名称：

  Multitarget Molecular Hybrids of Cinnamic Acids

  摘要：

  为了合成潜在的新型多靶点药物，合成了11种新型杂化物，其中包括肉桂酸和扑热息痛、4-/7-羟基香豆素、苯佐卡因、对氨基苯酚和间氨基苯酚。发现三种杂化物——2e、2a、2g——和3b是多功能药物。由苯氧苯基肉桂酸和间乙酰胺基苯酚衍生的杂化物2e显示出最高的脂氧合酶（LOX）抑制作用和镇痛活性（IC50 = 0.34 μΜ 和 98.1%），而溴苄氧基肉桂酸和二氢黄酮的杂化物3b同时表现出良好的LOX抑制活性（IC50 = 50 μΜ）和最高的抗蛋白酶活性（IC50 = 5 μΜ）。苯氧苯基酸与扑热息痛的杂化物2a显示出高镇痛活性（91%），并似乎是一种有前途的治疗周围神经损伤的药物。具有酯和酰胺键的杂化物2g呈现出有趣的抗LOX和抗蛋白酶活性组合。发现酯非常有效，尤其是那些由扑热息痛和间乙酰胺基苯酚衍生的酯。酰胺也紧随其后。基于二维结构-活性关系发现，立体电子参数在这些化合物的活性中起主要作用。分子对接研究表明，别构相互作用可能控制LOX抑制剂的结合。

  DOI：

  10.3390/molecules191220197
• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 作用下， 生成 4-[(4-溴苄基)氧基]苯甲醛
  参考文献：
  名称：

  使用氧化钼纳米颗粒作为有效且可回收的催化剂，生态合成4-芳基取代的吡喃并呋喃香豆素，作为潜在的药理活性杂环

  摘要：

  描述了通过使用氧化钼纳米颗粒（MoO 3 NPs）在4-羟基香豆素，丙二腈和各种芳基醛之间进行绿色级联三组分反应。通过这一成就，在绿色条件下一锅成功地合成了一些具有医学重要性的产品。获得良好或优异的产品收率，环境友好的程序，易于处理，原材料的可用性，使用无毒溶剂以及纳米催化剂的高回收率是这种方法的最重要优势。

  DOI：

  10.1007/s11164-018-3363-7

文献信息

• Small Multitarget Molecules Incorporating the Enone Moiety
  作者：Thalia Liargkova、Nikolaos Eleftheriadis、Frank Dekker、Efstathia Voulgari、Constantinos Avgoustakis、Marina Sagnou、Barbara Mavroidi、Maria Pelecanou、Dimitra Hadjipavlou-Litina

  DOI：10.3390/molecules24010199

  日期：——

  Chalcones represent a class of small drug/druglike molecules with different and multitarget biological activities. Small multi-target drugs have attracted considerable interest in the last decade due their advantages in the treatment of complex and multifactorial diseases, since “one drug-one target” therapies have failed in many cases to demonstrate clinical efficacy. In this context, we designed and synthesized potential new small multi-target agents with lipoxygenase (LOX), acetyl cholinesterase (AChE) and lipid peroxidation inhibitory activities, as well as antioxidant activity based on 2-/4- hydroxy-chalcones and the bis-etherified bis-chalcone skeleton. Furthermore, the synthesized molecules were evaluated for their cytotoxicity. Simple chalcone b4 presents significant inhibitory activity against the 15-human LOX with an IC50 value 9.5 µM, interesting anti-AChE activity, and anti-lipid peroxidation behavior. Bis-etherified chalcone c12 is the most potent inhibitor of AChE within the bis-etherified bis-chalcones followed by c11. Bis-chalcones c11 and c12 were found to combine anti-LOX, anti-AchE, and anti-lipid peroxidation activities. It seems that the anti-lipid peroxidation activity supports the anti-LOX activity for the significantly active bis-chalcones. Our circular dichroism (CD) study identified two structures capable of interfering with the aggregation process of Aβ. Compounds c2 and c4 display additional protective actions against Alzheimer’s disease (AD) and add to the pleiotropic profile of the chalcone derivatives. Predicted results indicate that the majority of the compounds with the exception of c11 (144 Å) can cross the Blood Brain Barrier (BBB) and act in CNS. The results led us to propose new leads and to conclude that the presence of a double enone group supports better biological activities.

  查耳酮类药物代表了一类具有多种和多重靶点生物活性的小分子药物或类药分子。在过去的十年里，小型多靶点药物因其能够治疗复杂和多因素疾病的优点而引起了相当大的兴趣，因为“一种药物一个靶点”的治疗方法在许多情况下未能显示出临床疗效。在这种情况下，我们设计并合成了具有潜在的新小型多靶点药物，具有脂氧合酶（LOX）、乙酰胆碱酯酶（AChE）和脂质过氧化抑制活性，以及基于2-/4-羟基查耳酮和双醚化双查耳酮骨架的抗氧化活性。此外，合成的分子还对其细胞毒性进行了评估。简单的查耳酮b4对15-人LOX具有显著的抑制活性，IC50值为9.5 µM，具有有趣的抗AChE活性和抗脂质过氧化行为。双醚化查耳酮c12是双醚化双查耳酮中对AChE最有效的抑制剂，其次是c11。发现双查耳酮c11和c12具有抗LOX、抗AchE和抗脂质过氧化活性。看来抗脂质过氧化活性支持显著活性的双查耳酮的抗LOX活性。我们的圆二色性（CD）研究发现两种结构能够干扰Aβ的聚集过程。化合物c2和c4显示了额外的保护作用，防止阿尔茨海默病（AD）的发生，并增加了查耳酮衍生物的多效性特征。预测结果表明，除了c11（144 Å）之外，大多数化合物能够穿越血脑屏障（BBB）并在中枢神经系统发挥作用。这些结果使我们提出了新的线索，并得出结论，存在一个双烯酮基团可以支持更好的生物活性。
• Multi-Target Cinnamic Acids for Oxidative Stress and Inflammation: Design, Synthesis, Biological Evaluation and Modeling Studies
  作者：Eleni Pontiki、Dimitra Hadjipavlou-Litina

  DOI：10.3390/molecules24010012

  日期：——

  multi-target cinnamic acids from the corresponding aldehydes with suitable 4-OH/Br substituted phenyl acetic acid by Knoevenagel condensation. The final products 1i, 3i, 3ii, 4i, 6i, 6ii, and 7i were obtained in high yields (52⁻98%) Their structures were verified spectrometrically, while their experimentally lipophilicity was determined as RM values. The novel derivatives were evaluated for their antioxidant

  炎症是一种复杂的现象，导致生物体对不同因素的愈合反应，产生免疫信号，过度的自由基活性和组织破坏。脂氧合酶及其代谢产物（如LTB₄）与过敏，细胞分化和致癌作用有关。脂氧合酶12/15被表征为IgA的粘膜特异性抑制剂，并且是过敏性致敏和气道炎症发展的原因。干扰这些代谢物形成或作用的药物的开发对于治疗各种疾病如哮喘，牛皮癣，溃疡性结肠炎，类风湿性关节炎，动脉粥样硬化，癌症和血管疾病非常重要。在这项研究中，我们扩展了先前的研究，通过Knoevenagel缩合反应，由相应的醛与合适的4-OH / Br取代的苯基乙酸合成了一系列多目标肉桂酸。最终产物1i，3i，3ii，4i，6i，6ii和7i以高收率（52％98％）获得。通过光谱法验证了其结构，而将其亲脂性实验确定为RM值。使用DPPH，羟基自由基，超氧阴离子和ABTS +•，抗脂质过氧化和大豆脂加氧酶抑制试验评估了这些新型衍生物的抗氧化活性。这些化
• Structure-activity studies on N -Substituted tranylcypromine derivatives lead to selective inhibitors of lysine specific demethylase 1 (LSD1) and potent inducers of leukemic cell differentiation
  作者：Johannes Schulz-Fincke、Mirjam Hau、Jessica Barth、Dina Robaa、Dominica Willmann、Andreas Kürner、Julian Haas、Gabriele Greve、Tinka Haydn、Simone Fulda、Michael Lübbert、Steffen Lüdeke、Tobias Berg、Wolfgang Sippl、Roland Schüle、Manfred Jung

  DOI：10.1016/j.ejmech.2017.12.001

  日期：2018.1

  overexpressed or deregulated in many cancers such as AML and prostate cancer and hence is a promising anticancer target with first inhibitors in clinical trials. Clinical candidates are N-substituted derivatives of the dual LSD1-/monoamine oxidase-inhibitor tranylcypromine (2-PCPA) with a basic amine function in the N-substituent. These derivatives are selective over monoamine oxidases. So far, only

  FAD 依赖性赖氨酸特异性去甲基化酶 1 (LSD1) 在许多癌症（如 AML 和前列腺癌）中过度表达或失调，因此是临床试验中具有第一个抑制剂的有前景的抗癌靶标。临床候选药物是双 LSD1-/单胺氧化酶抑制剂反苯环丙胺 (2-PCPA) 的 N 取代衍生物，在 N 取代基中具有碱性胺功能。这些衍生物对单胺氧化酶具有选择性。到目前为止，关于这一类重要的 LSD1 抑制剂的结构-活性研究只有非常有限的信息发表在同行评审的期刊上。在这里，我们表明没有基本功能甚至没有极性基团的 N 取代 2-PCPA 衍生物仍然是体外LSD1 的有效抑制剂并有效抑制培养中白血病细胞的集落形成。然而，这些亲脂性抑制剂还阻断结构相关的单胺氧化酶（MAO-A 和 MAO-B），这可能对治疗神经退行性疾病很有意义，但这种特性在癌症治疗中的应用并不理想。极性、非基本功能的引入导致优化结构，保留有效的 LSD1 抑制剂，但表现出对
• Ultrasound-assisted and Efficient Knoevenagel Condensation Reaction Catalyzed by Silica Sodium Carbonate Nanoparticles
  作者：Yaghoub Pourshojaei、Maryam Nikzad、Khalil Eskandari、Mohammad-Hossein Darijani、Abdolreza Hassanzadeh、Ehsan Faghih-Mirzaei、Ali Asadipour

  DOI：10.5562/cca3261

  日期：——

  malononitriles/methylcianoor ethylciano acetates in a onepot reaction catalyzed by silica sodium carbonate nanoparticles (SSC NPs) is described. In this reaction, SSC NPs demonstrated high efficiency as catalyst to obtain target products. By this achievement, a wide range of α,β-unsaturated compounds as Knoevenagel condensation products with good to excellent yields are obtained from reaction between numerous

  描述了在碳酸钠碳酸钠纳米颗粒（SSC NPs）催化的一锅法反应中合成亚芳基丙二腈/甲基ianozoyl或ethylciano乙酸酯的有效和超声辅助途径。在该反应中，SSC NPs作为获得目标产物的催化剂表现出很高的效率。通过该成就，通过许多芳醛与丙二腈，丙二酸甲酯或乙二酸乙酯的反应，获得了具有良好产率或优异产率的各种各样的，Knoevenagel缩合产物的α，β-不饱和化合物。以高收率和高纯度制备的目标产物可以作为重要的生物活性分子候选。该方法是合成所需产物的简便，廉价，快速且高效的方法。此外，催化剂从反应混合物中分离出来并在进一步运行中再利用的能力以及与绿色化学的相容性被认为是该方法的其他优点。所有产品均从其FT-IR和FT-NMR光谱及元素分析数据推导出。
• [EN] AGONISTS AND ANTAGONISTS OF THE S1P5 RECEPTOR, AND METHODS OF USES THEREOF<br/>[FR] AGONISTES ET ANTAGONISTES DU RÉCEPTEUR S1P5, ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ABBOTT LAB

  公开号：WO2010093704A1

  公开（公告）日：2010-08-19

  Disclosed are compounds that are agonists or antagonists of the S1P5 receptor, compositions comprising said compounds, and methods of using said compounds and compositions. In certain embodiments, said compounds are 1-benzylazetidine-3-carboxylic acid derivatives. In certain embodiments, said methods relate to the treatment of neuropatic pain and/or a neurodegenerative disorder. In certain embodiments, said compounds may be used in combination with a second therapeutic agent.

  本文披露了作为S1P5受体激动剂或拮抗剂的化合物，包括含有这些化合物的组合物，以及使用这些化合物和组合物的方法。在某些实施例中，这些化合物是1-苄基氮杂环丙氨酸衍生物。在某些实施例中，这些方法涉及治疗神经痛和/或神经退行性疾病。在某些实施例中，这些化合物可以与第二治疗剂结合使用。