4-(1H-吡咯-1-基)苯甲醛 | 23351-05-5

• 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 - 吡咯
• 中文名称: 4-(1H-吡咯-1-基)苯甲醛
• 中文别名: 4-吡咯-1-苯甲醛
• 英文名称: 4-(1H-pyrrol-1-yl)benzaldehyde
• 英文别名: 4-pyrrol-1-ylbenzaldehyde
• CAS: 23351-05-5
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: VMNADOXDGZJTBJ-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95°C
• 沸点：
  306.7±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 安全说明：
  S24/25
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  温度：2-8°C，保持在惰性气体氛围中。

SDS

Name:	4-(1h-pyrrol-1-yl)benzaldehyde 97% Material Safety Data Sheet
Synonym:
CAS:	23351-05-5

Section 1 - Chemical Product MSDS Name:4-(1h-pyrrol-1-yl)benzaldehyde 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
23351-05-5	4-(1H-Pyrrol-1-yl)benzaldehyde	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
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 water spray, dry chemical, carbon dioxide, or chemical 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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under an inert atmosphere.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 23351-05-5: 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: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 94 - 95 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: C11H9NO
Molecular Weight: 171.2

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 23351-05-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(1H-Pyrrol-1-yl)benzaldehyde - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 23351-05-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 23351-05-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 23351-05-5 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：

  4-(1H-吡咯-1-基)苯甲醛 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 45.0~100.0 ℃ 、405.3 kPa 条件下， 反应 9.0h， 生成 3-(4-Pyrrol-1-yl-phenyl)-propionic acid hydrazide
  参考文献：
  名称：

  Aromatic hydrazides as specific inhibitors of bovine serum amine oxidase

  摘要：

  New hydrazides were synthesized in search for specific inhibitors of bovine serum amine oxidase: a series of benzoic and phenylacetic acid hydrazides containing the 1H-imidazol-1-yl or the 1H-imidazol-1-ylmethyl group as (o, m, p)-substituent in the phenyl ring; an analogous series of p-substituted phenylhydrazides with 5 or 6-membered heterocyclic ring as substituent, and a series of similar phenylpropionic hydrazides. The longer and more flexible phenylacetic hydrazides, and to a somewhat lesser extent the phenylpropionic ones, were better specific inhibitors of bovine serum amine oxidase than the benzoic hydrazides, which were also bound by the enzyme with high affinity, but at a slow rate. Derivatives with p- and m -substituents were more reactive than the o-substituted ones. The chemical nature of the substituent was less important than its position in the phenyl ring and the presence of methylene spacers. These data point to the presence of a hydrophobic site at short distance from the protein carbonyl cofactor, so that simultaneous interaction of the 2 ends of the inhibitor molecule can occur at the 2 sites. The presence of the hydrophobic site was confirmed by the capability of some molecule deprived of the hydrazidic group to act as mild inhibitors. All hydrazides were less reactive by 2-3 orders of magnitude towards pig kidney diamine oxidase and FAD-dependent monoamine oxidase from rat brain mitochondria, while the other compounds showed similar inhibition power against all proteins. The specificity for the bovine enzyme seems therefore to be related to the concerted action of the 2 moieties of the inhibitor molecule.

  DOI：

  10.1016/0223-5234(92)90005-l
• 作为产物：
  描述：

  1-(4-碘苯基)吡咯 在 水 、 sodium formate 、 palladium diacetate 、 1,2-双(二苯基膦)乙烷 作用下， 以 二甲基亚砜 为溶剂， 生成 4-(1H-吡咯-1-基)苯甲醛
  参考文献：
  名称：

  由芳基卤和醛的钯催化合成的叔丁基胩使用甲酸盐作为氢化物供体†

  摘要：

  通过使用叔丁基异氰化物作为C 1资源和甲酸盐作为氢化物供体，无需任何其他碱，就已经实现了芳烃卤化物的高效一锅钯催化的芳基卤化物的加氢甲酰化反应。反应条件温和，易于操作且毒性较低，该反应可耐受各种官能团，产率中等至优异。

  DOI：

  10.1039/c4ra16388e

文献信息

• 一种靶向β淀粉样蛋白的荧光探针及制备以及其在阿尔兹海默症中的应用
  申请人：华南理工大学

  公开号：CN112920113B

  公开（公告）日：2022-08-16

  本发明公开了一种靶向β淀粉样蛋白的荧光探针及制备以及其在阿尔兹海默症中的应用。该荧光探针的结构式如式Ⅰ所示。本发明中的荧光探针是以6‑二甲氨基‑1‑甲基喹啉作为母体结构的化合物，该荧光探针具有发射波长长，Stock位移大，能特异性检β淀粉样蛋白，且对组织细胞中的粘度较为敏感，对粘度具有很好的响应，在与阿尔兹海默症患者脑内的β淀粉样蛋白结合后，荧光信号明显增强，可以用于检测β淀粉样蛋白和阿尔兹海默症的早期诊断，对于阿尔兹海默症诊疗探针的发展具有重要的指导意义。
• [EN] 1,4-DISUBSTITUTED PIPERIDINE DERIVATIVES AND THEIR USE AS 11-BETAHSD1 INHIBITORS<br/>[FR] DERIVES DE PIPERIDINE 1,4 DISUBSTITUEE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE 11-BETAHSD1
  申请人：ASTRAZENECA AB

  公开号：WO2004033427A1

  公开（公告）日：2004-04-22

  The use of a compound of formula (I) in the manufacture of a medicament for use in the inhibition of 11βHSD1 is described.

  使用式(I)的化合物制造用于抑制11βHSD1的药物。
• Characterization of Aminobenzylphenols as Protein Disulfide Isomerase Inhibitors in Glioblastoma Cell Lines
  作者：Andrea Shergalis、Ding Xue、Fatma Z. Gharbia、Hannah Driks、Binita Shrestha、Amina Tanweer、Kirin Cromer、Mats Ljungman、Nouri Neamati

  DOI：10.1021/acs.jmedchem.0c00728

  日期：2020.9.24

  Disulfide bond formation is a critical post-translational modification of newly synthesized polypeptides in the oxidizing environment of the endoplasmic reticulum and is mediated by protein disulfide isomerase (PDIA1). In this study, we report a series of α-aminobenzylphenol analogues as potent PDI inhibitors. The lead compound, AS15, is a covalent nanomolar inhibitor of PDI, and the combination of

  二硫键形成是在内质网氧化环境中新合成多肽的关键翻译后修饰，由蛋白质二硫键异构酶 (PDIA1) 介导。在这项研究中，我们报告了一系列 α-氨基苄基苯酚类似物作为有效的 PDI 抑制剂。先导化合物AS15是一种共价纳摩尔 PDI 抑制剂，AS15类似物与谷胱甘肽合成抑制剂丁硫氨酸亚砜亚胺 (BSO) 的组合可协同抑制细胞生长。使用新生的 RNA 测序，我们展示了一个AS15类似物触发胶质母细胞瘤细胞中未折叠的蛋白质反应。BODIPY 标记的类似物与包括 PDIA1 在内的蛋白质结合，表明这些化合物具有细胞渗透性并达到预期目标。总之，这些发现证明了一系列与 PDI 共价结合的高效活性小分子的广泛生化特征。
• Inhibitors of Acyl-CoA:Cholesterol <i>O</i>-Acyltransferase. 2. Identification and Structure−Activity Relationships of a Novel Series of <i>N</i>-Alkyl-<i>N</i>-(heteroaryl-substituted benzyl)-<i>N‘</i>-arylureas
  作者：Akira Tanaka、Takeshi Terasawa、Hiroyuki Hagihara、Yuri Sakuma、Noriko Ishibe、Masae Sawada、Hisashi Takasugi、Hirokazu Tanaka

  DOI：10.1021/jm9800853

  日期：1998.6.1

  tuted benzyl)-N'-arylurea and related derivatives represented by 2 and 3 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Among these novel compounds, the type 3 series was superior. A pyrazol-3-yl group on the N-benzyl group of this trisubstituted urea (i.e. 3, Ar1 =

  制备了一系列N-烷基-N-（杂芳基取代的苄基）-N'-芳基脲和相关的衍生物（用2和3表示），并对其在体外和体外抑制酰基辅酶A：胆固醇O-酰基转移酶的能力进行了评估。降低体内胆固醇喂养大鼠的血浆胆固醇水平。在这些新型化合物中，3型系列更为出色。该三取代脲的N-苄基上的吡唑-3-基（即3，Ar1 =吡唑-3-基）被鉴定为杂芳环，提供了良好的生物活性。通过优化与N-烷基（R）和N-芳基（Ar3）的组合的结果，化合物3aq（FR186054）被确定为一种新型的口服有效ACAT抑制剂，在胆固醇喂养的大鼠中表现出有效的体外ACAT抑制活性（兔子肠道微粒体IC50 = 99 nM）和出色的降胆固醇作用，而与给药方式无关（ED50 = 0.046 mg / kg，通过饮食给药，ED50 = 0. 44 mg /通过在PEG400载体中的管饲法施用1kg）。此外，一项毒理学研究表明，以10 mg / kg
• Regio- and <i>Trans</i>-Selective Ni-Catalyzed Coupling of Butadiene, Carbonyls, and Arylboronic Acids to Homoallylic Alcohols under Base-Free Conditions
  作者：Yu-Qing Li、Guang Chen、Shi-Liang Shi

  DOI：10.1021/acs.orglett.1c00488

  日期：2021.4.2

  We herein report a Ni-catalyzed three-component coupling of 1,3-butadiene, carbonyl compounds, and arylboronic acids as a general synthetic approach to 1,4-disubstituted homoallylic alcohols, an important class of compounds, which have previously not been straightforward to access. The reaction occurs efficiently using a Ni(cod)2 catalyst without any external base and ligand at ambient temperature

  我们在本文中报道了Ni催化的1,3-丁二烯，羰基化合物和芳基硼​​酸的三组分偶联，作为1,4-二取代的均丙醇的重要合成方法，这是一类重要的化合物，以前并不简单访问。使用Ni（cod）2催化剂可在环境温度下有效地进行反应，而无需使用任何外部碱和配体，并且可在一次操作中对原料丁二烯进行高度区域选择性和反选择性的1,4-二叉官能化。这个简单而实用的协议可以应用于广泛范围的基材。中性条件显示了对高度碱敏感的官能团的非凡耐受性。