5-氯-3-甲基-1-苯基吡唑-4-甲醛 | 947-95-5

• 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: 5-氯-3-甲基-1-苯基吡唑-4-甲醛
• 中文别名: 5-氯-3-甲基-1-苯基吡唑-4-烷醛
• 英文名称: 5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole
• 英文别名: 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde；5-chloro-3-methyl-1-phenylpyrazole-4-carbaldehyde
• CAS: 947-95-5
• 化学式: C₁₁H₉ClN₂O
• mdl: MFCD00100755
• 分子量: 220.658
• InChiKey: DKZPJLZXLKAMDO-UHFFFAOYSA-N

物化性质

• 熔点：
  145-148 °C (lit.)
• 沸点：
  356.1±37.0 °C(Predicted)
• 密度：
  1.26
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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
• WGK Germany：
  3
• 海关编码：
  2933199090
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将容器密封保存，并储存在阴凉干燥的地方。

SDS

Name:	5-Chloro-3-Methyl-1-Phenylpyrazole-4-Carboxaldehyde 99% Material Safety Data Sheet
Synonym:	None Known
CAS:	947-95-5

Section 1 - Chemical Product MSDS Name:5-Chloro-3-Methyl-1-Phenylpyrazole-4-Carboxaldehyde 99% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
947-95-5	5-Chloro-3-Methyl-1-Phenylpyrazole-4-C	99	unlisted

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

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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. Do NOT use mouth-to-mouth resuscitation.
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.
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 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# 947-95-5: 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: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 149 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: C11H9ClN2O
Molecular Weight: 220.5288

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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.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 947-95-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Chloro-3-Methyl-1-Phenylpyrazole-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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
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# 947-95-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 947-95-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 947-95-5 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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-氯-3-甲基-1-苯基吡唑	5-chloro-3-methyl-1-phenyl-1H-pyrazole	1131-17-5	C10H9ClN2	192.648

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride	188047-58-7	C11H8Cl2N2O	255.103
  5-氯-3-甲基-1-苯基-1H-吡唑-4-羧酸	3-methyl-1-phenyl-5-chloro-1H-pyrazole-4-carboxylic acid	1140-38-1	C11H9ClN2O2	236.658
  (5-氯-3-甲基-1-苯基-吡唑-4-基)甲醇	5-Chlor-3-methyl-4-hydroxymethyl-1-phenyl-pyrazol	1136-60-3	C11H11ClN2O	222.674
  5-氯-3-甲基-1-苯基-吡唑-4-腈	5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile	51626-33-6	C11H8ClN3	217.658
  ——	5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxaldehyde hydrazone	146254-77-5	C11H11ClN4	234.688
  ——	5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde hydrazone	146254-77-5	C11H11ClN4	234.688
  ——	[1-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-meth-(Z)-ylidene]-hydrazine	——	C11H11ClN4	234.688
  ——	5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde oxime	51626-34-7	C11H10ClN3O	235.673
  ——	1-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-phenylprop-2-yn-1-one	1370690-10-0	C19H13ClN2O	320.778
  ——	N,N'-bis-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazine	——	C22H18Cl2N6	437.331

反应信息

• 作为反应物：
  描述：

  5-氯-3-甲基-1-苯基吡唑-4-甲醛 在 氢溴酸 、 三乙酰氧基硼氢化钠 、 sodium carbonate 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 31.0h， 生成 特力利汀
  参考文献：
  名称：

  Process for the preparation of teneligliptin

  摘要：

  一种制备替格列奉的方法。

  公开号：

  US09518048B2
• 作为产物：
  描述：

  依达拉奉 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-氯-3-甲基-1-苯基吡唑-4-甲醛
  参考文献：
  名称：

  基于联吡唑的钯（II）配合物作为DNA嵌入剂和人工金属核酸酶

  摘要：

  摘要取代的3'-甲基-1'，2-二苯基-3,4-二氢-1' ħ，2 ħ -3,4'- bipyrazole及其正方形平面钯（II）型的配合物[钯（4 Ñ）氯2 ]，其中4 n  =联吡唑基配体，已经合成。这些化合物已通过多种技术进行了表征，例如元素分析，质量，吸收，IR，1 H NMR和1313 C NMR光谱。通过热重分析（TGA），电导测量和能量色散X射线光谱（EDX）对复合物进行了进一步分析。通过吸收滴定，粘度测量，溴化乙锭置换滴定和分子对接研究，研究了化合物与鲱鱼精子DNA之间的相互作用。已经根据K b，K sv和K f值检查了化合物与DNA之间的结合强度。相互作用的自发性已通过评估热力学参数（如吉布的自由能，焓变（ΔH °）和熵变（ΔS）进行了检查°）。已经通过凝胶电泳技术评估了复合物的质粒切割功效。已经评估了化合物对病原体例如金黄色葡萄球菌，大肠杆菌，枯草芽孢杆菌，marces

  DOI：

  10.1007/s00706-018-2316-6

文献信息

• Synthesis of poly-functionalized pyrazoles under Vilsmeier-Haack reaction conditions
  作者：Aleksandr V. Popov、Valentina A. Kobelevskaya、Ludmila I. Larina、Igor B. Rozentsveig

  DOI：10.24820/ark.5550190.p010.934

  日期：——

  Synthesis of 1,3-disubstituted 5-chloro-1H-pyrazole-4-carbaldehydes was achieved by formylation of the corresponding 5-chloro-1H-pyrazoles under Vilsmeier-Haack conditions.

  1,3-二取代的 5-氯-1H-吡唑-4-甲醛的合成是通过在 Vilsmeier-Haack 条件下相应的 5-氯-1H-吡唑的甲酰化来实现的。
• Design, synthesis, molecular modelling, ADME prediction and anti-hyperglycemic evaluation of new pyrazole-triazolopyrimidine hybrids as potent α-glucosidase inhibitors
  作者：Vinay Pogaku、Kiran Gangarapu、Srinivas Basavoju、Kiran Kumar Tatapudi、Suresh Babu Katragadda

  DOI：10.1016/j.bioorg.2019.103307

  日期：2019.12

  The aim of the present study is to design and synthesis of new pyrazole-triazolopyrimidine hybrids as potent α-glucosidase inhibitors. The target compounds 4a-n were synthesized by one-pot multicomponent approach with good yields and were characterized by various spectroscopic techniques and finally by single crystal X-ray diffraction method (4j). All the newly-synthesized derivatives have been screened

  本研究的目的是设计和合成作为有效的α-葡萄糖苷酶抑制剂的新型吡唑-三唑并嘧啶杂化物。目标化合物4a-n是通过一锅多组分法合成的，收率很高，并通过各种光谱技术进行了表征，最后通过单晶X射线衍射法进行了表征（4j）。已经筛选了所有新合成的衍生物的α-葡萄糖苷酶抑制活性，并以阿卡波糖为标准药物。在所有测试的化合物中，4h表现出优异的α-葡萄糖苷酶抑制活性，相对于标准药物阿卡波糖（IC 50：12.68μM），IC 50值为12.45μM 。同样，化合物4f图1a和4l显示出有效活性，IC 50值分别为14.47μM和17.27μM。建立了所有标题化合物的结构-活性关系（SAR）研究。研究了α-葡萄糖苷酶与化合物之间的结合相互作用方式。预测了目标化合物的类药物特性（Lipinski参数和in silico ADME特性）。化合物4h，4f和4l的α-葡萄糖苷酶抑制作用，分子对接和类药物性质被认为是抗糖尿病活性的有希望的命中方法。
• Design, synthesis and evaluation of dihydrotriazine derivatives-bearing 5-aryloxypyrazole moieties as antibacterial agents
  作者：Tian-Yi Zhang、Chun-Shi Li、Ming-Yue Cui、Xue-Qian Bai、Jiang-Hui Chen、Ze-Wen Song、Bo Feng、Xue-Kun Liu

  DOI：10.1007/s11030-020-10071-9

  日期：2021.5

  study implied that compound 10d exerted its antibacterial activity through DHFR inhibition. Moreover, significant inhibition of biofilm formation was observed in bacterial cells treated with MIC conc. of 10d as visualized by SEM micrographs. Graphic abstract Twenty-nine target compounds were designed, synthesized and evaluated in terms of their antibacterial and antifungal activities.

  摘要 在本研究中，合成了一系列带有 5-芳氧基吡唑部分的二氢三嗪衍生物，并通过不同的光谱工具确认了它们的结构。体外生物学评价表明，与参比药物相比，部分目标化合物具有良好的抗菌和抗真菌活性。在这些新型杂交体中，化合物10d显示出最有效的活性，对金黄色葡萄球菌4220、MRSA 3506 和大肠杆菌1924 菌株的最小抑制浓度值 (MIC) 为 0.5 µg/mL 。化合物6d , 6m , 10d和10g的细胞毒活性在 MCF-7 和 HeLa 细胞中进行评估。生长动力学研究表明，当用不同浓度处理时，可显着抑制细菌生长。的10D。体外酶研究表明化合物10d通过抑制DHFR发挥抗菌活性。此外，在用 MIC conc 处理的细菌细胞中观察到生物膜形成的显着抑制。的10D的SEM照片的可视化。 图形摘要 设计、合成了 29 种目标化合物，并评估了它们的抗菌和抗真菌活性。
• Synthesis and Evaluation on Anticonvulsant Activities of Pyrazolyl Semicarbazones
  作者：Xian-Qing Deng、Ming-Xia Song、Hai-Hong Yu

  DOI：10.14233/ajchem.2014.18218

  日期：——

  In this paper, a series of 2-[(5-phenoxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-methylene]hydrazine carboxamides were synthesized and evaluated for their anticonvulsant activities using the maximal electroshock method. Their neurotoxicities were determined applying the rotarod test. Interestingly, all compounds showed anticonvulsant activity with long duration of protection effects in the maximal electroshock test. Among which, compound 5m was found to have promising anticonvulsant activity, which gave an ED50 of 42.4 mg/kg and a protective index value of 3.7, possessing better anticonvulsant activity and higher safety than marketed drugs valproate, but weaker than phenobarbital. Furthermore, the antagonistic activity against seizures induced by pentylenetetrazole of the compound 5m was also established, which suggested that compound 5m may exert anticonvulsant activity through g-aminobutyric acid (GABA)-mediated mechanisms.

  本文中，我们合成了一系列2-[(5-苯氧基-3-甲基-1-苯基-1H-吡唑-4-基)-亚甲基]酰肼羧酰胺，并利用最大电休克法评估了它们的抗惊厥活性。通过旋转棒试验测定了它们的中枢神经毒性。有趣的是，所有化合物在最大电休克试验中均显示出抗惊厥活性，且保护效果持久。其中，化合物5m表现出有前景的抗惊厥活性，其ED50为42.4 mg/kg，保护指数值为3.7，抗惊厥活性优于市场药物丙戊酸，但弱于苯巴比妥，并且安全性更高。此外，化合物5m对戊四氮诱导的惊厥也有拮抗活性，这表明化合物5m可能通过γ-氨基丁酸（GABA）介导的机制发挥抗惊厥作用。
• Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives: assessment of their antimicrobial, antituberculosis and antioxidant activity
  作者：Chetan B. Sangani、Jigar A. Makwana、Yong-Tao Duan、Nilesh J. Thumar、Meng-Yue Zhao、Yogesh S. Patel、Hai-Liang Zhu

  DOI：10.1007/s11164-015-2138-7

  日期：2016.3

  A new series of pyrazolo[1,2-b]phthalazine derivatives (4a–p) bearing the 5-aryloxypyrazole nucleus was synthesized by one-pot, three-component, base-catalyzed cyclo condensation reaction of 3-methyl-5-aryloxy-1-aryl-1H-pyrazole-4-carbaldehyde (1a–d), malononitrile or ethyl cyanoacetate (2a–b) and 2,3-dihydro-1,4-phthalazinedione (3a–b) in ethanol containing an eco friendly base, NaOH, in good to excellent yields. All synthesized compounds (4a–p) were duly characterized by physico-chemical parameters, 1H NMR, 13C NMR, FT-IR and LCMS techniques. In vitro antimicrobial activity of the synthesized compounds was investigated against a representative panel of pathogenic strains. Compounds 4e, 4g, 4h, 4k and 4o exhibited excellent antimicrobial activity compared with first line drugs. In vitro antituberculosis activity was evaluated against Mycobacterium tuberculosis H37Rv, and compounds 4g and 4o emerged as the promising antimicrobial members with better antituberculosis activity. A brine shrimp bioassay was carried out to study the in vitro cytotoxic properties of the synthesized compounds. In vitro antioxidant activity was evaluated by the ferric-reducing antioxidant power method. Compounds 4c, 4d, 4g and 4h showed the highest antioxidant potencies.

  通过一步法、三组分、碱催化的环缩合反应，以3-甲基-5-芳氧基-1-芳基-1H-吡唑-4-甲醛（1a–d）、丙二腈或氰乙酸乙酯（2a–b）和2,3-二氢-1,4-酞嗪二酮（3a–b）为原料，在含环保碱NaOH的乙醇中合成了含5-芳氧基吡唑核的一系列新型吡唑并[1,2-b]酞嗪衍生物（4a–p），产率良好至优秀。所有合成的化合物（4a–p）均通过物理化学参数、1H NMR、13C NMR、FT-IR和LCMS技术进行了适当表征。对合成的化合物进行了体外抗菌活性测试，针对一组有代表性的病原菌株进行了研究。与一线药物相比，化合物4e、4g、4h、4k和4o表现出优异的抗菌活性。体外抗结核活性针对结核分枝杆菌H37Rv进行了评估，化合物4g和4o作为有前景的抗菌成员，显示出更好的抗结核活性。通过盐水虾生物测定法研究了合成化合物的体外细胞毒性。通过铁还原抗氧化能力法评估了体外抗氧化活性。化合物4c、4d、4g和4h表现出最高的抗氧化活性。