3,5-二甲基-1苯基吡唑-4-噻吩甲醛 | 22042-79-1

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3,5-二甲基-1苯基吡唑-4-噻吩甲醛
• 中文别名: 3,5-二甲基-1苯基吡唑-4-甲醛；3,5-二甲基-1-苯基吡唑-4-噻吩甲醛
• 英文名称: 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 4-Formyl-3,5-dimethyl-1-phenylpyrazol；3,5-dimethyl-1-phenyl-4-formylpyrazole；3,5-dimethyl-1-phenylpyrazole-4-carbaldehyde
• CAS: 22042-79-1
• 化学式: C₁₂H₁₂N₂O
• mdl: MFCD00051396
• 分子量: 200.24
• InChiKey: VOMRTQQGXWPTJK-UHFFFAOYSA-N

物化性质

• 熔点：
  125-128 °C
• 沸点：
  337.96°C (rough estimate)
• 密度：
  1.1131 (rough estimate)
• 溶解度：
  溶于DMSO、甲醇
• 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)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 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：
  Xn,Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933199090
• 安全说明：
  S22,S26,S36/37/39
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  存于阴凉干燥处

SDS

Name:	3 5-Dimethyl-1-Phenylpyrazole-4-Carboxal-Dehyde 99% Material Safety Data Sheet
Synonym:	None known
CAS:	22042-79-1

Section 1 - Chemical Product MSDS Name:3 5-Dimethyl-1-Phenylpyrazole-4-Carboxal-Dehyde 99% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
22042-79-1	3,5-Dimethyl-1-Phenylpyrazole-4-Carbox	99.0	244-750-9

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. 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.
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. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. 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# 22042-79-1: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: buff
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 122.00 - 124.00 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:
Specific Gravity/Density:
Molecular Formula: C12H12N2O
Molecular Weight: 200.24

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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# 22042-79-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,5-Dimethyl-1-Phenylpyrazole-4-Carboxal-Dehyde - 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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 22042-79-1: No information available.
Canada
CAS# 22042-79-1 is listed on Canada's NDSL List.
CAS# 22042-79-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 22042-79-1 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,5-二甲基-1苯基吡唑-4-噻吩甲醛 在 硫酸 、 水 、 一氯化碘 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 64.5h， 生成
  参考文献：
  名称：

  Synthesis of some substituted furan-2(5H)-ones and derived quinoxalinones as potential anti-microbial and anti-cancer agents

  摘要：

  In search for novel anti-cancer and anti-microbial agents with promising pharmacotoxicological profile, the synthesis of some substituted 4-halofuran-2(5H)-ones (8a-l, 9, 11) and derived halogenated quinoxalin-2(1H)-ones (12a-d) is described. Some of the halogenated furanones were readily oxidized to the corresponding 2-bromo-2-propenoic acids (13a-c) with hydrogen peroxide in alkaline medium. Twenty-two compounds were preliminary tested for their in vitro activity against three bacteria and one fungus and revealed encouraging activity. On the other hand, three compounds were screened as anti-cancer agents using cell line panel protocol and 22 compounds were subjected to cycline-dependent kinases (CDKs) inhibition screening program but were inactive.

  DOI：

  10.1007/s00044-010-9394-2
• 作为产物：
  描述：

  苯肼 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 3,5-二甲基-1苯基吡唑-4-噻吩甲醛
  参考文献：
  名称：

  Revolutionary Pyrazole‐based Aza‐BODIPY: Harnessing Photothermal Power Against Cancer Cells and Bacteria

  摘要：

  摘要 在癌症治疗和细菌感染治疗领域，光热疗法（PTT）作为一种潜在策略脱颖而出。然而，目前面临的挑战是如何制造出既能成像又能进行 PTT 的光热制剂，即所谓的治疗剂。由于近红外光在生物组织中具有广泛的穿透力，吸收和发射近红外波段（750-900 纳米）的光热制剂最近受到了广泛关注。在这项研究中，我们将吡唑与杂-BODIPY（PY-AZB）结合起来，开发出了一种新型光热剂。PY-AZB具有很好的光稳定性，光热转换效率（PCE）高达33%。此外，根据共聚焦图像显示，PY-AZB 能在 6 小时内以快速积累的速度渗透癌细胞。此外，体外光热疗法结果表明，PY-AZB 能有效消除高达 70% 的癌细胞。有趣的是，PY-AZB 对革兰氏阴性菌大肠杆菌 780 和革兰氏阳性菌金黄色葡萄球菌 1466 都具有抗菌活性。结果表明，PY-AZB 对细菌具有令人满意的杀菌效果，在激光照射下的杀灭率高达 100%。因此，PY-AZB 可以为光热治疗提供一种可行的选择。

  DOI：

  10.1002/cbic.202300653

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。
• Synthesis and Biological Evaluation of New Pyrazole-based Thiazolyl Hydrazone Derivatives as Potential Anticancer Agents
  作者：Mehlika Altıntop、Ahmet Ozdemir、Sinem Ilgın、Ozlem Atli

  DOI：10.2174/1570180811666140226235350

  日期：2014.6

  pyrazole-based thiazolyl hydrazone derivatives were obtained via the ring closure reaction of 3,5- dimethyl-1H-1-phenylpyrazole-4-carboxaldehyde thiosemicarbazone with 2-bromoacetophenone derivatives. The compounds were investigated for their cytotoxic effects on A549 and NIH3T3 cell lines. Among these compounds, compound 2i bearing a trifluoromethyl substituent can be identified as the most promising

  通过3,5-二甲基-1H-1苯基吡唑-4-甲醛甲醛缩氨基脲与2-溴苯乙酮衍生物的闭环反应获得了新的吡唑基噻唑基ly衍生物。研究了这些化合物对A549和NIH3T3细胞系的细胞毒性作用。在这些化合物中，带有三氟甲基取代基的化合物2i可被鉴定为最有前途的抗A549癌细胞系的抗癌剂。化合物2i对A549细胞具有抑制作用，IC 50值为0.0316 mM，而顺铂则具有抗癌活性，IC 50值为0.01 mM。根据IC 50 值，化合物2i对A549细胞的抑制作用与其对NIH3T3细胞的作用相比可以认为是选择性的。
• Synthesis of<i>N</i>-phenylpyrrole and pyrazole amidines and related diamines
  作者：Richard L. Jarvest、Joanne E. Marshall

  DOI：10.1002/jhet.5570290605

  日期：1992.10

  N-Phenylpyrrole and pyrazole nitriles 3,4,10 were prepared in one step from the corresponding aldehydes. The nitriles were converted into novel amidines 5,6,14 and related diamines 7,8,12 were also prepared from the aldehydes. The orientation of the phenyl ring to the basic function was controlled by modifying the torsional angle between the rings by methyl group substitution on the heterocycle.

  由相应的醛一步制备N-苯基吡咯和吡唑腈3,4,10。将腈转化为新颖的am 5、6、14，并从醛中制备相关的二胺7、8、12。苯环相对于基本功能的取向是通过通过杂环上的甲基取代来改变环之间的扭转角来控制的。
• trans -3,4-Dimethyl-4-(3-carboxamidophenyl)piperidines: A novel class of μ-Selective opioid antagonists
  作者：Bertrand Le Bourdonnec、Serge Belanger、Joel A. Cassel、Gabriel J. Stabley、Robert N. DeHaven、Roland E. Dolle

  DOI：10.1016/j.bmcl.2003.09.012

  日期：2003.12

  trans-3,4-Dimethyl-4-(3-carboxamidophenyl)piperidines constitute a novel class of micro opioid receptor antagonists. The CONH(2) group was found to be an effective isostere of the phenolic OH moiety. Structure-activity relationships at the piperidine nitrogen position led to the identification of several ligands displaying high affinity toward the cloned human micro opioid receptors, good selectivity

  反式-3,4-二甲基-4-（3-羧酰胺基苯基）哌啶构成了一类新型的微阿片受体拮抗剂。发现CONH（2）组是酚OH部分的有效等排体。在哌啶氮位置的结构活性关系导致鉴定了几个配体，这些配体对克隆的人微阿片样物质受体具有高亲和力，良好的选择性micro / delta，micro / kappa和有效的体外拮抗剂活性。
• [EN] PYRAZOLE DERIVATIVES<br/>[FR] DERIVES DE PYRAZOLE
  申请人：DAIICHI SEIYAKU CO

  公开号：WO2006013939A1

  公开（公告）日：2006-02-09

  A compound represented by the general formula (I), which is useful as a peroxisome proliferator-activated receptor α/Ϝ agonist, a salt of the compound, and a solvate of either. (In the formula, X, Y, and Z each represents nitrogen or carbon; m is an integer of 0 to 3; n is an integer of 1 to 3; Q represents a benzene ring optionally substituted by hydroxy, halogeno, lower alkenyl, lower alkoxy, lower alkyl, and amino; R1 represents a phenyl, naphthyl, or 5- or 6-membered aromatic heterocyclic group optionally substituted by hydroxy, halogeno, lower alkenyl, lower alkoxy, phenoxy, phenyl, lower alkyl, and amino; R2 represents lower alkyl, carbamoyl, phenyl, or a 5- or 6-membered aromatic heterocyclic group; R3 and R4 each represents hydrogen or lower alkyl; R5 represents hydrogen, lower alkyl, or benzyl; and R6 represents hydrogen, hydroxy, halogeno, lower alkenyl, lower alkoxy, phenoxy, phenyl, lower alkyl, or amino

  通用公式（I）表示的化合物，可用作过氧化物酶体增殖物激活受体α/Ϝ激动剂，该化合物的盐，以及任一种的溶剂。 （在公式中，X、Y和Z分别表示氮或碳；m为0至3的整数；n为1至3的整数；Q表示苯环，可选择地由羟基，卤素，较低烯基，较低烷氧基，较低烷基和氨基取代；R1表示苯基，萘基或可选择地由羟基，卤素，较低烯基，较低烷氧基，苯氧基，苯基，较低烷基和氨基取代的5-或6-成员芳香杂环基；R2表示较低烷基，氨基甲酰基，苯基或5-或6-成员芳香杂环基；R3和R4分别表示氢或较低烷基；R5表示氢，较低烷基或苄基；R6表示氢，羟基，卤素，较低烯基，较低烷氧基，苯氧基，苯基，较低烷基或氨基

表征谱图