4-(吡唑-1-基)苯甲醛 | 99662-34-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(吡唑-1-基)苯甲醛
• 中文别名: 1-(4-甲酰基苯基)吡唑；4-吡唑-1-基苯甲醛；1-(4-甲醛基苯基)吡唑；1-(4-甲醛基苯基) 吡唑
• 英文名称: 4-(1H-pyrazol-1-yl)benzaldehyde
• 英文别名: 4-(pyrazol-1-yl)benzaldehyde；4-(1H-pyrazolyl)benzaldehyde；4-pyrazol-1-ylbenzaldehyde
• CAS: 99662-34-7
• 化学式: C₁₀H₈N₂O
• mdl: MFCD02681938
• 分子量: 172.186
• InChiKey: PPGRDLZPSDHBIC-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83°C
• 沸点：
  310.1±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)
• 溶解度：
  9.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  34.9
• 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
• 危险类别码：
  R36/37/38
• 海关编码：
  2933199090
• 安全说明：
  S24/25
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Name:	4-(1h-pyrazol-1-yl)benzaldehyde 95+% Material Safety Data Sheet
Synonym:
CAS:	99662-34-7

Section 1 - Chemical Product MSDS Name:4-(1h-pyrazol-1-yl)benzaldehyde 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
99662-34-7	4-(1H-Pyrazol-1-yl)benzaldehyde	95+%	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# 99662-34-7: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 84 - 85 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: C10H8N2O
Molecular Weight: 172.19

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing 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# 99662-34-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(1H-Pyrazol-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# 99662-34-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 99662-34-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 99662-34-7 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-(吡唑-1-基)苯甲醛 在 三乙基硼 、 水 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-(4-羟甲基苯基)吡唑
  参考文献：
  名称：

  组合KOH / BEt 3催化剂用于芳香族羧酰胺的选择性脱氨加氢硼化反应以构建发光体

  摘要：

  酰胺选择性催化C–N键裂解为增值胺产品是一种理想的但具有挑战性的转化。含有亚氨基二苄基基序的分子普遍存在于药物分子和功能材料中。在这里，我们建立了一种组合的KOH / BEt 3催化剂，用于将酰基-亚氨基二苄基衍生物（包括非杂环羧酰胺）进行脱氨基硼氢化成相应的胺。这种新颖的无过渡金属的方法也被用于氯米帕明和发光体的构建。

  DOI：

  10.1021/acs.orglett.0c03033
• 作为产物：
  描述：

  4-(1H-吡唑基)苯腈 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 以55%的产率得到4-(吡唑-1-基)苯甲醛
  参考文献：
  名称：

  Synthesis and biological investigations of dopaminergic partial agonists preferentially recognizing the D4 receptor subtype

  摘要：

  Aminomethyl-substituted biaryls bearing a pyrazole or triazole moiety were synthesized and investigated for dopamine and serotonin receptor binding. The N-arylpyrazoles 3b,f,g and 4 revealed K-i values in the subnanomolar range (0.28-0.70 nM) for the dopamine D4 receptor subtype. Employing both mitogenesis and GTP gamma S assays, ligand efficacy was evaluated indicating partial agonist properties. Interestingly, the tetrahydropyrimidine 4 (FAUC 2020) displayed significant intrinsic selectivity for D2(long) over D2(short). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.075
• 作为试剂：
  描述：

  4-(吡唑-1-基)苯甲醛 、 [(3-aminomethylphenoxy)]acetic acid isopropyl ester 在 4-(吡唑-1-基)苯甲醛 作用下， 以65的产率得到isopropyl [3-({[4-(1H-pyrazol-1-yl)benzyl]amino}methyl)-phenoxy]acetate
  参考文献：
  名称：

  EP2 agonists

  摘要：

  本发明提供EP2受体激动剂，其制备方法，含有这些化合物的药物组合物，以及使用这些化合物和组合物降低眼压从而治疗青光眼的方法。

  公开号：

  US07622475B2

文献信息

• Substituent Group Variations Directing the Molecular Packing, Electronic Structure, and Aggregation-Induced Emission Property of Isophorone Derivatives
  作者：Zheng Zheng、Zhipeng Yu、Mingdi Yang、Feng Jin、Qiong Zhang、Hongping Zhou、Jieying Wu、Yupeng Tian

  DOI：10.1021/jo400116j

  日期：2013.4.5

  ring or aza-crown-ether group, with large Stokes shifts (>140 nm), have been synthesized and characterized. 1–4 display aggregation-induced emission behaviors, while dye 5 is highly emissive in solution but quenched in the solid state. It was found that the tuning of emission color of the isophorone-based compounds in the solid state could be conveniently accomplished by changing the terminal substituent

  一系列新的异佛尔酮衍生物（的1 - 5），收纳该杂环或氮杂冠醚基团，具有大的斯托克斯位移（> 140纳米），已经合成和表征。1 - 4显示聚集诱导的发射行为，而染料5在溶液中高发射性，但在固体状态下猝灭。已经发现，通过改变末端取代基可以方便地实现固态的基于异佛尔酮的化合物的发射颜色的调节。对溶液，水悬浮液和晶态的光物理性质及其关系进行了比较研究。的晶体学数据1 - 4指示相邻分子之间的多个分子间氢键键合相互作用的存在限制了分子内振动和旋转，使化合物1 - 4在固态强烈发射。使用扫描电子显微镜研究了不同水含量的颗粒的大小和生长过程，表明水悬浮液中较小的球形纳米颗粒有利于荧光发射。以上结果表明，取代基对它们的分子堆积，电子结构和聚集诱导的发射性质有很大的影响。此外，荧光细胞成像实验证明了5的潜在应用。
• Nickel-Catalyzed Markovnikov Transfer Hydrocyanation in the Absence of Lewis Acid
  作者：Nils L. Frye、Anup Bhunia、Armido Studer

  DOI：10.1021/acs.orglett.0c01454

  日期：2020.6.5

  Hydrocyanation in the absence of toxic HCN gas is highly desirable. Addressing that challenge, transition-metal-catalyzed transfer hydrocyanation using safe HCN precursors has been developed, but these reagents generally require a Lewis acid for activation, and the control of regioselectivity often remains problematic. In this Letter, a Ni-catalyzed highly Markovnikov-selective transfer hydrocyanation

  在没有有毒的HCN气体的情况下进行氢氰化是非常需要的。为了应对这一挑战，已经开发出使用安全的HCN前体的过渡金属催化的转移氢氰化反应，但是这些试剂通常需要路易斯酸进行活化，并且对区域选择性的控制通常仍然存在问题。在这封信中，报道了在没有任何路易斯酸的情况下进行的镍催化的高度马尔可夫尼科夫选择性转移氢氰化反应。易制得的原芳族1-异丙基环己-2,5-二烯-1-腈作为HCN源，该反应显示出较宽的底物范围和较高的官能团耐受性。将末端苯乙烯衍生物，二烯和内部炔烃以良好的选择性转化为优异的选择性。机理研究为区域选择性的起源提供了见识。
• Parallel Solution-Phase Synthesis and General Biological Activity of a Uridine Antibiotic Analog Library
  作者：Omar Moukha-chafiq、Robert C. Reynolds

  DOI：10.1021/co4001452

  日期：2014.5.12

  coupling of the amino terminus of d-phenylalanine methyl ester to the free 5′-carboxylic acid moiety of 33 followed by sodium hydroxide treatment led to carboxylic acid analog 77. Hydrolysis of this material gave analog 78. The intermediate 77 served as the precursor for the preparation of novel dipeptidyl uridine analogs 79–99 through peptide coupling reactions to diverse amine reactants. None of the described

  在 NIH 路线图计划的中试规模库 (PSL) 计划下，以溶液相方式从胺2和羧酸33和77合成了一个包含 94 种尿苷抗生素类似物的小型库。多样醛，磺酰氯，和羧酸反应物套缩合，2，酸介导的水解导致后，向目标化合物3 - 32以良好的收率和高的纯度。同样，用不同的胺和磺胺处理33得到34 – 75。d氨基末端的偶联-苯丙氨酸甲酯到33的游离 5'-羧酸部分，然后用氢氧化钠处理产生羧酸类似物77。该材料的水解得到类似物78。中间77担任该前体为二肽基新颖尿苷类似物的制备79 - 99通过肽偶联到不同的胺反应剂反应。所描述的化合物均未显示出显着的抗癌或抗疟活性。通过 NIH MLPCN 计划提供和报告的初级筛选中的酶和受体，许多样品表现出各种有希望的抑制性、激动剂、拮抗剂或激活剂特性。
• [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。
• Accessing Difluoromethylated and Trifluoromethylated <i>cis</i> ‐Cycloalkanes and Saturated Heterocycles: Preferential Hydrogen Addition to the Substitution Sites for Dearomatization
  作者：Xue Zhang、Liang Ling、Meiming Luo、Xiaoming Zeng

  DOI：10.1002/anie.201907457

  日期：2019.11.18

  Reported here is a straightforward process in which a cyclic (alkyl)(amino)carbene/Rh catalyst system facilitates the preferential addition of hydrogen to the substitution sites of difluoromethylated and trifluoromethylated arenes and heteroarenes, leading to dearomative reduction. This strategy enables the diastereoselective synthesis of cis-difluoromethylated and cis-trifluoromethylated cycloalkanes

  此处报道的是一种简单的方法，其中环状（烷基）（氨基）卡宾/ Rh催化剂体系有助于将氢优先添加到二氟甲基化和三氟甲基化的芳烃和杂芳烃的取代位上，从而导致脱芳族还原反应。该策略使非对映选择性合成顺式-二氟甲基化和顺式-三氟甲基化的环烷烃和饱和的杂环，甚至允许形成具有定义的赤道取向的二-和三氟甲基的全顺式多-三氟甲基化的环状产物。氘标记研究表明，氢优先攻击平面芳烃的取代位，从而导致脱芳香化作用，可能以异质Rh为反应性物种，