3-苯基-1H-吡唑-4-甲醛 | 26033-20-5

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-苯基-1H-吡唑-4-甲醛
• 中文别名: 3-苯基吡唑-4-甲醛
• 英文名称: 3-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-phenyl-4-formylpyrazole；3-phenyl-4-pyrazole carboxaldehyde；3-Phenyl-1H-pyrazole-4-carboxaldehyde；5-phenyl-1H-pyrazole-4-carbaldehyde
• CAS: 26033-20-5
• 化学式: C₁₀H₈N₂O
• mdl: MFCD00216971
• 分子量: 172.186
• InChiKey: OCCFXKQCKSLEII-UHFFFAOYSA-N

物化性质

• 熔点：
  146-148 °C
• 沸点：
  302.5°C (rough estimate)
• 密度：
  1.1841 (rough estimate)
• 溶解度：
  10.3 [ug/mL]
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933199090
• WGK Germany：
  3
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  应密闭储存在阴凉、干燥的环境中。

SDS

Name:	3-Phenyl-1H-Pyrazole-4-Carboxaldehyde 98% (HPLC) Material Safety Data Sheet
Synonym:	4-Formyl-3-Phenylpyrazole
CAS:	26033-20-5

Section 1 - Chemical Product MSDS Name:3-Phenyl-1H-Pyrazole-4-Carboxaldehyde 98% (HPLC) Material Safety Data Sheet
Synonym:4-Formyl-3-Phenylpyrazole

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
26033-20-5	3-Phenyl-1H-Pyrazole-4-Carboxaldehyde	98%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. No information found.
The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. 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.
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:

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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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. 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:
Wash thoroughly after handling. Use only in a well-ventilated area.
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.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 26033-20-5: 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: Powder
Color: light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 140 - 144 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: 25 MG/ML (100C)
Specific Gravity/Density:
Molecular Formula: C10H8N2O
Molecular Weight: 172.19

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 26033-20-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Phenyl-1H-Pyrazole-4-Carboxaldehyde - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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# 26033-20-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 26033-20-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 26033-20-5 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：

  3-苯基-1H-吡唑-4-甲醛 在 sodium hydroxide 、 potassium permanganate 作用下， 以 水 为溶剂， 以98%的产率得到5-苯基-1H-吡唑-4-羧酸
  参考文献：
  名称：

  3-取代的芳基吡唑-4-羧酸的合成

  摘要：

  提出了一种制备以前未知的3-芳基取代的吡唑-4-羧酸的方法，该方法包括将26种可用的单和双取代的苯乙酮和2-乙酰基噻吩的半咔唑的Vilsmeier甲酰化，然后氧化所得的3-芳基取代的吡唑-。 4-羧醛在高锰酸钾的作用下。讨论了甲酰化反应的机理。该方法即使对含有烷基取代基的苯乙酮也能成功地起作用。在后一种情况下，使用另外的步骤，该步骤涉及分离吡唑-4-羧酸作为其甲硅烷基酯。

  DOI：

  10.1007/s11176-005-0318-7
• 作为产物：
  描述：

  苯乙酮缩氨基脲 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-苯基-1H-吡唑-4-甲醛
  参考文献：
  名称：

  具有0D，1D，2D和3D骨架 的M（ii）苯基取代的吡唑羧酸酯配合物的结构多样性和性质†

  摘要：

  八种被两种苯基取代的新型金属配合物 吡唑羧酸，[Ni（HL 1）2（H 2 O）2 ]（1），[Cu（HL 1）2（H 2 O）2 ]（2），[Zn（HL 1）2 ]（3），[ Ni（HL 2）2（H 2 O）2 ]（4），[Ni（HL 2）2（HL 3）2 ]（5），[Cu（HL 2）2 ]·2H 2 O（6）， [锌（HL2） 2 ]（ 7），[Zn 2（HL 2） 2（L 2）]（ 8）[H 2 L 1 = 5-苯基-1 H-吡唑-3-羧酸；H 2 L 2＝ 3-苯基-1 H-吡唑-4-羧酸；H 2 L 2＝ 3。通过水/溶剂热反应制备HL 3＝ 3-苯基-1 H-吡唑]并对其结构进行表征。配合物1和2具有单体结构；图3和图4显示1-D之字形链；5和6具有由菱形网格组成的2D层结构；7具有2倍互穿的3-D菱形框架；而复合物8则具有类似3-D NaCl的框架。氢键键合和芳族π-π堆积相

  DOI：

  10.1039/c0nj00904k

文献信息

• Design, Synthesis, and Biological Evaluation of the Combinatorial Library with a New Spirodiketopiperazine Scaffold. Discovery of Novel Potent and Selective Low-Molecular-Weight CCR5 Antagonists
  作者：Hiromu Habashita、Masaya Kokubo、Shin-ichi Hamano、Nobuyuki Hamanaka、Masaaki Toda、Shiro Shibayama、Hideaki Tada、Kenji Sagawa、Daikichi Fukushima、Kenji Maeda、Hiroaki Mitsuya

  DOI：10.1021/jm060051s

  日期：2006.7.1

  anti-HIV activity. Herein, we describe in detail the identification of these lead compounds using a combinatorial chemistry approach. A novel spirodiketopiperazine scaffold was designed on the basis of the concept of the privileged structure of G-protein-coupled receptors (GPCRs). This new framework was obtained in acceptable yield with high purity from the readily prepared isonitrile resin through

  我们之前曾报道发现有几种螺二酮哌啶衍生物作为具有抗HIV活性的有效CCR5拮抗剂。在本文中，我们详细描述了使用组合化学方法鉴定这些先导化合物的方法。基于G蛋白偶联受体（GPCR）的优先结构的概念，设计了一种新型的螺二酮哌嗪骨架。通过Ugi反应，顺序转化和环化裂解，可以从容易制备的异腈树脂中以高收率获得可接受的高纯度新骨架。通过测量初始文库中每种化合物对MIP-1alpha刺激的细胞内钙动员的抑制活性，发现了几种化合物显示出适度但有选择性的CCR5拮抗活性。
• Design, synthesis, and biological evaluation of 1, 3-disubstituted-pyrazole derivatives as new class I and IIb histone deacetylase inhibitors
  作者：Yiwu Yao、Chenzhong Liao、Zheng Li、Zhen Wang、Qiao Sun、Chunping Liu、Yang Yang、Zhengchao Tu、Sheng Jiang

  DOI：10.1016/j.ejmech.2014.09.024

  日期：2014.10

  A novel series of HDAC inhibitors demonstrating class I and IIb subtype selectivity have been identified using a scaffold-hopping strategy. Several designed compounds showed better selectivity for class I and IIb over class IIa HDAC isoforms comparing to the FDA approved HDAC targeting drug SAHA. A representative lead compound 22 bearing a biphenyl moiety demonstrated promising class I and IIb HDAC

  使用脚手架跳槽策略已鉴定出一系列新的HDAC抑制剂，可证明I类和IIb类亚型选择性。与FDA批准的HDAC靶向药物SAHA相比，几种设计的化合物对I和IIb的选择性优于IIa类的HDAC同工型。带有联苯部分的代表性铅化合物22表现出有希望的I和IIb类HDAC同工型选择性和对几种癌细胞的体外抗癌活性。这项工作可以作为使用设计的分子支架进一步探索选择性HDAC抑制剂的基础平台。
• Regeneration of Carbonyl Compounds from Oximes Using BTBAD under Microwave Irradiation
  作者：R. Murugan、B. S. R. Reddy

  DOI：10.1246/cl.2004.1038

  日期：2004.8

  Bis-tetrabutylammonium dichromate (BTBAD) has been found to be an efficient and new reagent for the conversion of oximes to the corresponding carbonyl compounds. The reaction was performed under microwave irradiation and gave excellent yields. It also facilitates the de-protection of acetals and ketals.

  已发现双四丁基重铬酸铵 (BTBAD) 是一种有效的新试剂，可用于将肟转化为相应的羰基化合物。该反应在微波辐射下进行，产率极好。它还有助于缩醛和缩酮的脱保护。
• [EN] 1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES, PREPARATIONS THEREOF AND USES THEREOF<br/>[FR] DERIVES DE 1,2,3,4-TETRAHYDROISOQUINOLINE, LEURS PREPARATIONS ET LEURS UTILISATIONS
  申请人：ASTRAZENECA AB

  公开号：WO2005061484A1

  公开（公告）日：2005-07-07

  Compounds of general formula (I) wherein D, E, R1, R2, R3, R4, R5, R6 and R7 are as defined in the specification, as well as salts, enantiomers thereof and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  通式（I）的化合物，其中D、E、R1、R2、R3、R4、R5、R6和R7如规范中所定义，以及盐、对映体以及包括这些化合物的药物组合物已经制备。它们在治疗中很有用，特别是在疼痛管理中。
• Thienopyrrolidinones
  申请人：——

  公开号：US20020028841A1

  公开（公告）日：2002-03-07

  The invention is directed to substituted thieno[2,3-b]pyrrolidin-5-ones. The compounds are useful as inhibitors of cellular production of tumor necrosis factor (TNF-&agr;) and as antiproliferative agents. These compounds are useful in the treatment or control of neuro-degenerative diseases, cardiovascular diseases, cancer or inflammatory diseases.

  本发明涉及取代的噻吩并[2,3-b]吡咯烷-5-酮化合物。这些化合物可作为细胞肿瘤坏死因子（TNF-α）生成的抑制剂和抗增殖剂。它们在治疗或控制神经退行性疾病、心血管疾病、癌症或炎症性疾病方面具有应用价值。