5-(3-硝基苯基)糠醛 | 13148-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(3-硝基苯基)糠醛
• 中文别名: 5-(3-硝基苯)-2-呋喃醛
• 英文名称: 5-(3-nitrophenyl)furfural
• 英文别名: 5-(3-nitrophenyl)furan-2-carbaldehyde；5-(3-nitrophenyl)-2-furaldehyde；5-(3-nitro-phenyl)-furan-2-carboaldehyde
• CAS: 13148-43-1
• 化学式: C₁₁H₇NO₄
• mdl: MFCD00046106
• 分子量: 217.181
• InChiKey: DXUACWQWQDJZMY-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C(lit.)
• 溶解度：
  6.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 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：
  76
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2932190090
• 危险类别：
  IRRITANT
• 安全说明：
  S26,S36
• 储存条件：
  2-8°C

SDS

Name:	5-(3-Nitrophenyl)furfural Material Safety Data Sheet
Synonym:	5-(3-Nitrophenyl)-2-furancarboxaldehyde
CAS:	13148-43-1

Section 1 - Chemical Product MSDS Name:5-(3-Nitrophenyl)furfural Material Safety Data Sheet
Synonym:5-(3-Nitrophenyl)-2-furancarboxaldehyde

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13148-43-1	5-(3-Nitrophenyl)furfural	100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38 44

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin. Risk of explosion if heated under confinement.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Risk of explosion if heated under confinement.
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. 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. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 13148-43-1: 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:
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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 156 - 158 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: C11H7NO4
Molecular Weight: 217.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions. Risk of explosion if heated under confinement.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
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# 13148-43-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-(3-Nitrophenyl)furfural - 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: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
R 44 Risk of explosion if heated under confinement.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 13148-43-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13148-43-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13148-43-1 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：

  5-(3-硝基苯基)糠醛 在 哌啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以80%的产率得到5-(3'-nitrophenyl)furan-2-carbaldehyde oxime
  参考文献：
  名称：

  Synthesis of Arylfurfural Oximes and Their Biological Evaluation

  摘要：

  通过元素分析和光谱技术（傅立叶变换红外光谱、1H NMR、13C NMR 和质谱），制备并表征了各种芳基糠醛肟。对合成的化合物进行了抗氧化、酪氨酸酶和化学胰蛋白酶活性测试。

  DOI：

  10.14233/ajchem.2016.19624
• 作为产物：
  描述：

  2-糠醛缩二乙醇 在 palladium on activated charcoal 正丁基锂 、 三乙胺 作用下， 以 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-(3-硝基苯基)糠醛
  参考文献：
  名称：

  A Practical One-Pot Synthesis of 5-Aryl-2-furaldehydes

  摘要：

  描述了一种有用的一锅法合成5-芳基-2-呋喃醛的方法，该方法通过钯介导的铃木偶联反应将芳基卤化物与原位生成的5-(二乙氧基甲基)-2-呋喃硼酸结合。该程序具有广泛的适用性，能够提供高产率，并且易于放大。

  DOI：

  10.1055/s-2001-16759

文献信息

• Synthesis and In Vitro Evaluation of Furan-Based Chalcone Derivatives as Antimicrobial Agents
  作者：Ahmet Ozdemir、Mehlika Dilek Altıntop、Zerrin Canturk、Zafer Asim Kaplancikli

  DOI：10.2174/1570180812999150202112352

  日期：2015.6.6

  Some furan-based chalcone derivatives were synthesized via the Claisen-Schmidt condensation of 5-arylfurfural derivatives with 4'-cyanoacetophenone. The synthesized derivatives were investigated for their antimicrobial activity using a broth microdilution assay. Among these compounds, 1-(4-cyanophenyl)-3-[5-(4-nitrophenyl)-2-furyl]-2-propen-1-one (4) can be considered as the most promising antimicrobial agent against Enterococcus faecalis (ATCC 51922) and Candida albicans. Compound 4 showed antimicrobial activity against E. faecalis with a MIC value of 100 µg/mL, whereas chloramphenicol exhibited its antibacterial activity with a MIC value of 200 g/mL. Compound 4 (MIC = 100 µg/mL) was also more effective than ketoconazole (MIC = 200 µg/mL) against C. albicans. Microbiological assay pointed out the importance of p-nitro substituent for antimicrobial activity.

  通过Claisen-Schmidt缩合反应，将5-芳基糠醛衍生物与4'-氰基苯乙酮反应，合成了一些基于呋喃查耳酮的衍生物。使用肉汤微量稀释法对合成的衍生物进行了抗微生物活性研究。在这些化合物中，1-(4-氰基苯基)-3-[5-(4-硝基苯基)-2-呋喃基]-2-丙烯-1-酮（4）可被认为是对粪肠球菌（ATCC 51922）和白色念珠菌最具潜力的抗微生物剂。化合物4对粪肠球菌的MIC值为100 µg/mL，而氯霉素的抗菌活性MIC值为200 g/mL。化合物4（MIC = 100 µg/mL）对白色念珠菌的效力也优于酮康唑（MIC = 200 µg/mL）。微生物学分析指出了对硝基取代基对抗微生物活性的重要性。
• Oxadiazolopyrazine derivatives as pharmaceutically active compounds
  申请人：4SC AG

  公开号：EP1529531A1

  公开（公告）日：2005-05-11

  The present invention relates to furazanopyrazine derivatives of the general formula (I): wherein: R' represents -NR1R2 or -OR9 R" represents -NR5-NR3R4, -NR5-ORb, -O-NR3R4; wherein R1 to R9 in formula (1) represent independently of each other a variety of different substituents comprising alkyl, aryl, aralkyl, alkylaryl, heteroaryl groups and monofunctional moieties.

  本发明涉及一般式(I)的呋嗪吡唑衍生物： 其中： R'代表-NR1R2或-OR9 R"代表-NR5-NR3R4，-NR5-ORb，-O-NR3R4； 其中式(1)中的R1至R9分别独立地代表各种不同取代基，包括烷基、芳基、芳基烷基、烷基芳基、杂环芳基和单官能团。
• 5-Aryl-2-furancarbaldehyde Hydrazones and Related Compounds
  作者：Alžbeta Krutošíková、Miloslava Dandárová、Juraj Alföldi

  DOI：10.1135/cccc19931905

  日期：——

  A series of 5-aryl-2-furancarbaldehyde 2,6-dialkylphenylhydrazones (Ia - Iv) and dimethylhydrazones (IIa - IIf) as well as related compound benzo[b]furan-2-carbaldehyde dimethylhydrazone (III) were prepared. Compounds Ia - Iv were synthesized by condensing 5-aryl-2-furancarbaldehydes with 2,6-dialkylphenylhydrazines, compounds IIa - IIf were obtained from the same starting compounds and N,N-dimethylhydrazine. The intermediate 5-aryl-2-furancarbaldehydes were prepared by reaction of aryldiazonium chlorides with 2-furancarbaldehyde. The structure of the compounds were proven by ¹H, ¹³C and ¹⁵N NMR spectra.

  一系列5-芳基-2-呋喃甲醛2,6-二烷基苯基腙（Ia - Iv）和二甲基腙（IIa - IIf）以及相关化合物苯并[b]呋喃-2-甲醛二甲基腙（III）已经制备。化合物Ia - Iv通过5-芳基-2-呋喃甲醛与2,6-二烷基苯基腙缩合合成，化合物IIa - IIf则来自相同起始化合物和N,N-二甲基腙。中间体5-芳基-2-呋喃甲醛通过芳基重氮氯化物与2-呋喃甲醛反应制备。这些化合物的结构通过1H、13C和15N核磁共振谱得到证实。
• [EN] PHENYLALANINE DERIVATIVES AND THEIR USE AS NON-PEPTIDE GLP-1 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS PHÉNYLALANINES ET LEUR UTILISATION COMME MODULATEURS NON PEPTIDIQUES DU RÉCEPTEUR DE GLP-1
  申请人：ARGUSINA INC

  公开号：WO2011094890A1

  公开（公告）日：2011-08-11

  Provided herein are non-peptide GLP-1 receptor modulator compounds, for example, of Formula (I), pharmaceutical compositions comprising such compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of a metabolic disorder.

  本文提供了非肽类GLP-1受体调节剂化合物，例如，Formula (I)的化合物，包括这些化合物的药物组合物，以及其制备方法。还提供了这些化合物用于治疗代谢紊乱的方法。
• Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy
  作者：Xia Zhou、Yuping Tan、Kun Gou、Lei Tao、Yuan Luo、Yue Zhou、Zeping Zuo、Qingxiang Sun、Youfu Luo、Yinglan Zhao

  DOI：10.1016/j.bioorg.2021.105159

  日期：2021.10

  adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest

  丝氨酸是从头合成嘌呤和脱氧胸苷所必需的一碳单元的来源，在癌细胞的生长中起着至关重要的作用。磷酸甘油酸脱氢酶 (PHGDH) 催化丝氨酸从头生物合成中的第一个限速步骤，已成为治疗癌症的有希望的靶点。在这里，我们从基于酶促测定的内部小分子库的筛选中确定了H-G6作为潜在的 PHGDH 抑制剂。我们采用了活性导向的组合化学合成策略来优化这种命中化合物。发现化合物b36是非竞争性和最有前途的化合物，其对 PHGDH 的IC 50值为 5.96 ± 0.61 μM。化合物b36抑制人乳腺癌和卵巢癌细胞的增殖，减少细胞内丝氨酸合成，破坏DNA合成，并诱导细胞周期停滞。总的来说，我们的结果表明b36是一种新型的 PHGDH 抑制剂，它可能是一种有前景的调节丝氨酸合成途径的调节剂，并且可能是一种潜在的抗癌先导物，值得进一步探索。