109925-10-2

Basic information

• Product Name: 1,3-Dimethyl-5-phenoxy-1H-pyrazole-4-carboxaldehyde
• Synonyms: 1,3-Dimethyl-5-phenoxy-1H-pyrazole-4-carboxaldehyde;1，3-dimethyl-5-plenoxy-1 H-pyrazole-4-carboxaldehyde;1,3-dimethyl-5-phenoxypyrazole-4-carbaldehyde
• CAS NO: 109925-10-2
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.24
• Mol File: 109925-10-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Dimethyl-5-phenoxy-1H-pyrazole-4-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethyl-5-phenoxy-1H-pyrazole-4-carboxaldehyde(109925-10-2)
• EPA Substance Registry System: 1,3-Dimethyl-5-phenoxy-1H-pyrazole-4-carboxaldehyde(109925-10-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 109925-10-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Dimethyl-5-phenoxy-1H-pyrazole-4-carboxaldehyde is used as a key intermediate in the synthesis of pharmaceuticals for its potential anti-inflammatory and antitumor properties. Its incorporation into drug molecules can enhance their therapeutic effects, making it a valuable component in the development of new medications.
Used in Agrochemical Industry:
In the agrochemical sector, 1,3-Dimethyl-5-phenoxy-1H-pyrazole-4-carboxaldehyde is utilized as a precursor in the production of agrochemicals, potentially contributing to the development of more effective pesticides or herbicides that can combat various agricultural pests and weeds.
Used in Organic Synthesis:
As a building block in organic synthesis, 1,3-Dimethyl-5-phenoxy-1H-pyrazole-4-carboxaldehyde is employed to construct a variety of complex organic molecules. Its unique structure allows for the creation of new compounds with diverse applications in various industries.
Used in Medicinal Chemistry:
In medicinal chemistry, 1,3-Dimethyl-5-phenoxy-1H-pyrazole-4-carboxaldehyde is used as a starting material for the design and synthesis of novel bioactive molecules. Its versatility in chemical reactions facilitates the exploration of new drug candidates with improved pharmacological profiles.

Upstream product

• 27006-76-4 5-chloro-4-formyl-1,3-dimethylpyrazole 
• 108-95-2 phenol 
• 5203-77-0 1,3-dimethyl-1H-pyrazol-5-ol 
• 2749-59-9 1,3-dimethyl-5-pyrazolone 

Downstream Products

• 110035-28-4 1,3-dimethyl-5-phenoxy-1H-pyrazole-4-carbaldehyde oxime 
• 1620883-58-0 C₂₃H₂₁ClN₄O₃S 
• 149054-60-4 (CH₃)C₃N₂(OC₆H₅)(CH₃)COOH 
• 1424330-09-5 C₂₂H₂₄N₄O₂ 
• 126763-67-5 1,3-dimethyl-5-phenoxypyrazol-4-carboaldoxime O-2,6,6-trimethylhept-2-ene-4-ynyl ether 
• 111812-58-9 fenpyroximate 
• 149054-67-1 1,3-dimethyl-5-phenoxypyrazole-4-carbaldehyde oxime 

Relevant articles and documents

Design of a simple and efficient synthesis for bioactive novel pyrazolyl-isoxazoline hybrids

A simple and new methodology has been developed for the synthesis of novel bioactive pyrazolyl-isoxazoline hybrids from a pyrazolyl-substituted oxime and various substituted allyloxybenzenes, which are easily available, inexpensive starting materials. All the novel synthesized target hybrids were characterized by NMR, IR, and mass spectroscopic techniques. We have employed some of the hybrid materials in anti-bacterial and anti-fungal activity studies. The hybrid materials 6m and 6p exhibited the best anti-bacterial and anti-fungal activities.

Synthesis and evaluation of anticonvulsant activities of pyrazol semicarbazones. Part II

A series of 2-((5-aryloxy-1-methyl-3-methyl-1H-pyrazol-4-yl)methylene) hydrazinecarboxamides (6a-6l) and 2-((5-aryloxy-1-methyl-3-phenyl-1H-pyrazol-4-yl)methylene) hydrazinecarboxamides (7a-7l) were designed and synthesized. The maximal electroshock shock (MES) and subcutaneous pentylenetetrazole (sc-PTZ) seizure models in mice were used to evaluate the antiepileptic effect of compounds synthesized. Further, the acute neurotoxicity profile was also studied via the rotarod test. The results of sc-PTZ test indicate that a majority of compounds possessed anticonvulsant activity with long duration of protection effects. Among of them, compound 6k was found to be the most promising one, with an ED50 value of 20.4 mg/kg (in sc-PTZ model) and a PI value of 10.8, possessing higher anti-PTZ activity and wider safety margin than valproate and ethosuximide.

Synthesis and bioactivities of novel pyrazole oxime derivatives containing a 5-trifluoromethylpyridyl moiety

In this study, in order to find novel biologically active pyrazole oxime compounds, a series of pyrazole oxime derivatives containing a 5-trifluoromethylpyridyl moiety were synthesized. Preliminary bioassays indicated that most title compounds were found to display good to excellent acaricidal activity against Tetranychus cinnabarinus at a concentration of 200 μg/mL, and some designed compounds still showed excellent acaricidal activity against Tetranychus cinnabarinus at the concentration of 10 μg/mL, especially since the inhibition rates of compounds 8e, 8f, 8l, 8m, 8n, 8p, and 8q were all 100.00%. Interestingly, some target compounds exhibited moderate to good insecticidal activities against Plutella xylostella and Aphis craccivora at a concentration of 200 μg/mL; furthermore, compounds 8e and 8l possessed outstanding insecticidal activities against Plutella xylostella under the concentration of 50 μg/mL.

Discovery and structure-activity relationship study of 4-phenoxythiazol-5-carboxamides as highly potent TGR5 agonists

A novel therapy that stimulates endogenous glucagon-like peptide-1 (GLP-1) secretion by Takeda G-protein-coupled receptor 5 (TGR5) agonists might be a superior alternative for the treatment of type 2 diabetes mellitus. A series of 4-phenoxythiazol-5-carboxamides were developed as highly potent TGR5 agonists using a bioisosteric replacement strategy based on the scaffold of 4-phenoxynicotinamides. The structure-activity relationship on the bottom phenyl ring and the thiazole ring was extensively studied, and the 2-methylthiazole derivatives 30c and e displayed the best in vitro potency toward human TGR5, with EC50 values of approximately 1 nM. While endowed with excellent in vitro potency, the 2-methyl-thiazoles were flawed with high microsomal clearance.

Synthesis and biological activities of novel 1,3,4-thiadiazole-containing pyrazole oxime derivatives

A new library of 1,3,4-thiadiazole-containing pyrazole oximes was designed and synthesized. Their acaricidal and insecticidal activities were evaluated. Bioassay results indicated that some target compounds exhibited good acaricidal and insecticidal properties. Especially, compound 8m had 80% acaricidal activity against Tetranychus cinnabarinus at the concentration of 50?μg/mL, compound 8f displayed 100% insecticidal activities against Aphis craccivora at the concentration of 50?μg/mL, compounds 8r and 8w showed 100% insecticidal activities against Plutella xylostella at the concentration of 50?μg/mL. Furthermore, compounds 8r (LC50?=?19.61?μg/mL) and 8w (LC50?=?9.78?μg/mL) possessed comparable or even better insecticidal activities than the control Pyridalyl (LC50?=?17.40?μg/mL) against P. xylostella.

The thiazoylmethoxy modification on pyrazole oximes: Synthesis and insecticidal biological evaluation beyond acaricidal activity

A series of new pyrazole oximes bearing substituted thiazole ring were designed and prepared. The structures of the title compounds were identified by spectral analyses. The results of primary bioassay indicated that some targeted compounds exhibited promising insecticidal activity besides acaricidal activity, particularly; compounds 8c and 8d were more potent against Tetranychus cinnabarinus and Plutella xylostella than other analogues.

Discovery of 5-phenoxy-1,3-dimethyl-1H-pyrazole-4-carboxamides as potent agonists of TGR5 via sequential combinatorial libraries

Optimization of a high-throughput screening hit led to the discovery of a new series of 5-phenoxy-1,3-dimethyl-1H-pyrazole-4-carboxamides as highly potent agonists of TGR5. This novel chemotype was rapidly developed through iterative combinatorial library synthesis. It was determined that in vitro agonist potency correlated with functional activity data from human peripheral blood monocytes.

Identification of antitumor activity of pyrazole oxime ethers

A series of pyrazole oxime ether derivatives were prepared and examined as cytotoxic agents. In particular, 5-phenoxypyrazole was comparable to doxorubicin, while exhibiting very potent cytotoxicity against XF 498 and HCT15.

Introduction of N-containing heterocycles into pyrazole by nucleophilic aromatic substitution

The nucleophilic aromatic substitution on 5-chloropyrazoles activated by the electron-withdrawing formyl group offers a useful method to introduce a wide range of N-containing heterocycles into them. The rate of reaction was greatly affected by the electronic nature of the N-1 substitution.