219986-65-9

Basic information

• Product Name: 3-(4-BROMOPHENYL)-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE
• Synonyms: AKOS BBS-00000210;3-(4-BROMOPHENYL)-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE
• CAS NO: 219986-65-9
• Molecular Formula: C₁₀H₆BrF₃N₂
• Molecular Weight: 291.07
• Mol File: 219986-65-9.mol

Chemical Properties

• Melting Point: 163-168°C
• Boiling Point: 383.6±42.0 °C(Predicted)
• Appearance: /
• Density: 1.654±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 9.36±0.10(Predicted)
• CAS DataBase Reference: 3-(4-BROMOPHENYL)-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-BROMOPHENYL)-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE(219986-65-9)
• EPA Substance Registry System: 3-(4-BROMOPHENYL)-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE(219986-65-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 219986-65-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
3-(4-Bromophenyl)-5-(Trifluoromethyl)-1h-Pyrazole is used as a key intermediate in the synthesis of pharmaceuticals for its potential biological activities. Its unique structure allows for the development of new drugs with specific therapeutic effects.
Used in Agrochemical Research and Development:
In the agrochemical industry, 3-(4-Bromophenyl)-5-(Trifluoromethyl)-1h-Pyrazole is used as a starting material for the creation of new agrochemicals, potentially leading to more effective and targeted pest control solutions.
Used in Organic Synthesis:
3-(4-Bromophenyl)-5-(Trifluoromethyl)-1h-Pyrazole is utilized as a building block in the synthesis of other organic compounds, contributing to the development of novel chemical entities with various applications across different industries.
Used in Medicinal Chemistry Research:
3-(4-Bromophenyl)-5-(Trifluoromethyl)-1h-Pyrazole is employed in medicinal chemistry research to explore its potential biological activities and to understand its interactions with biological targets, which may lead to the discovery of new therapeutic agents.

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 99-90-1 para-bromoacetophenone 
• 1122-91-4 4-bromo-benzaldehyde 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 219986-60-4 3-(4-bromo-phenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-pyrazole-1-carbothioic acid amide 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 2236129-81-8 trifluoroacetaldehyde N-triftosylhydrazone 
• 366014-14-4 (E)-4-(4-bromophenyl)-1,1,1-trifluoro-3-buten-2-one 
• 18931-61-8 4,4,4-trifluoro-1-(4-bromophenyl)butane-1,3-dione 
• 7803-57-8 hydrazine hydrate 

Downstream Products

• 1454290-69-7 ethyl 2-(5-(3'-(methylthio)-[1,1'-biphenyl]-4-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate 
• 1454288-88-0 ethyl 2-(5-(3’-(methylsulfonyl)-[1,1’-biphenyl]-4-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate 
• 1454288-89-1 ethyl 2-(4-bromo-5-(3'-(methylsulfonyl)biphenyl-4-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate 
• 1454288-90-4 2-(5-(3'-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid 
• 1454288-91-5 2-(dimethylamino)ethyl 2-(5-(3'-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate 
• 1454288-92-6 2-(dimethylamino)ethyl 2-(4-bromo-5-(3'-(methylsulfonyl)biphenyl-4-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate 
• 1454288-93-7 (methylthio)methyl 2-(5-(3'-(methylsulfonyl)biphenyl-4-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate 
• 1454288-94-8 (methylthio)methyl 2-(4-bromo-5-(3'-(methylsulfonyl)biphenyl-4-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate 
• 1454288-98-2 ethyl 2-(5-(4'-(hydroxymethyl)-3'-(methylsulfonyl)biphenyl-4-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate 
• 1454290-67-5 ethyl 2-(5-(4-bromophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate 
• 929899-45-6 3-(4-bromo-phenyl)-1-ethyl-5-trifluoromethyl-1H-pyrazole 

Relevant articles and documents

Regioselective Synthesis of 3-Trifluoromethylpyrazole by Coupling of Aldehydes, Sulfonyl Hydrazides, and 2-Bromo-3,3,3-trifluoropropene

A general and practical strategy for 3-trifluoromethylpyrazole synthesis is reported that occurs by the three-component coupling of environmentally friendly and large-tonnage industrial feedstock 2-bromo-3,3,3-trifluoropropene (BTP), aldehydes, and sulfonyl hydrazides. This highly regioselective three-component reaction is metal-free, catalyst-free, and operationally simple and features mild conditions, a broad substrate scope, high yields, and valuable functional group tolerance. Remarkably, the reactions could be performed on a 100 mmol scale and smoothly afforded the key intermediates for the synthesis of celecoxib, mavacoxib, SC-560, and AS-136A. Preliminary mechanism studies indicated that a 1,3-hydrogen atom transfer process was involved in this transformation.

Cycloaddition of Trifluoroacetaldehyde N-Triftosylhydrazone (TFHZ-Tfs) with Alkynes for Synthesizing 3-Trifluoromethylpyrazoles

A transition-metal-free [3 + 2] cycloaddition between trifluoroacetaldehyde N-triftosylhydrazone (TFHZ-Tfs) and alkynes is reported. This protocol provides an operationally simple and general method for the synthesis of diverse 3-trifluoromethylpyrazoles in good to excellent yields with broad substrate scope, including aryl, heteroaryl, and alkyl terminal alkynes, and electron-deficient internal alkynes. The synthetic potential of this method was further demonstrated by the synthesis of an antiarthritic drug Celecoxib in multigram scale.

Synthetic method of novel trifluoromethyl pyrazole compound

The invention belongs to the technical field of organic synthesis chemistry, and relates to a synthetic method of a trifluoromethyl pyrazole compound. The compound can be used for synthesizing a variety of drugs, pesticides and bioactive molecules, so that synthesis and application of the compound are focused. According to the preparation method disclosed by the invention, a simple easily-available raw material acetylene compound and N-trifluoroacetaldehyde phenylsulfonyl hydrazone are used for efficiently synthesizing the three-dimensional specific trifluoromethyl pyrazole compound by one step under a condition without metal catalysis. The method disclosed by the invention has the characteristics that the raw materials are simple and easily available, the range is wide, metal catalysts are not needed, massive synthesis is achieved, the operation method is simple, the reaction is efficient, and the product has a specific three-dimensional structure; and industrial synthesis can be realized.

HETEROCYCLIC COMPOUNDS AS FUNGICIDES

The present invention relates to novel heterocyclic compound of Formula (I), (I) wherein, Het, L1, A, L2 and R12 are as defined in the detailed description, for use as fungicides.

An efficient route to 3-trifluoromethylpyrazole via cyclization/1,5-H shift and its applications in the synthesis of bioactive compounds

A methodology for regioselective synthesis of 3-trifluoromethylpyrazole from the reaction of trifluoromethyl alkenone and tosylhydrazone has been developed. The reaction was proposed to proceed through a tandem cyclization and 1,5-H shift reaction, which can be applied to the synthesis of bioactive compounds like Celecoxib, Mavacoxib, and SC-560.

LIVER X RECEPTOR (LXR) MODULATORS

Described herein are liver X receptor (LXR) modulators and methods of utilizing LXR modulators in the treatment of LXR-associated diseases, disorders or conditions. Also described herein are pharmaceutical compositions containing such compounds.

LIVER X RECEPTOR (LXR) MODULATORS FOR THE TREATMENT OF DERMAL DISEASES, DISORDERS AND CONDITIONS

Described herein are liver X receptor (LXR) modulators and methods of utilizing LXR modulators in the treatment of dermal diseases, disorders or conditions. Also described herein are pharmaceutical compositions containg such compounds.

Silver-mediated cycloaddition of alkynes with CF3CHN 2: Highly regioselective synthesis of 3-trifluoromethylpyrazoles

Silver screen: The title reaction provides a convenient and efficient method for the construction of 5-substituted 3-trifluoromethylpyrazoles under mild reaction conditions. By using this protocol, the marketed drug Celecoxib (antiarthritic) could be easily synthesized (see scheme; DMF=N,N- dimethylformamide). Copyright

NOVEL C3A RECEPTOR ANTAGONISTS

Aryl substituted imidazo[4,5-c] pyridine compounds are provided. These compounds are useful in pharmaceutical compositions as C3a antagonists for treating a variety of medical conditions associated with the Complement cascade. Methods for treating such conditions are also provided.

Haloacetylated enol ethers 10. Condensation of β-alkoxyvinyl trifluoromethyl ketones with thiosemicarbazide. Synthesis of new trifluoromethyl 4,5-dihydro-1H-1-pyrazolethiocarboxyamides

The synthesis of 3-aryl[alkyl]-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1- pyrazolethiocarboxyamides (2a-g) from the direct cyclo-condensation reaction of β-alkoxyvinyl trifluoromethyl ketones (1a-g) with thiosemicarbazide in methanol, under mild conditions, is reported. Similarly, the 1H-1-pyrazolethiocarboxyamide derivatives (2a-g) were easily dehydrated and the thiocarboxyamide group hydrolyzed in a one-step reaction by stirring with concentrated sulfuric acid to give the 3-aryl[alkyl]-5-trifluoromethyl-1H-pyrazoles (3a-g) in good yields. Specific syntheses and physical properties of 3-aryl[alkyl]-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1- pyrazolethiocarboxyamides are reported here for the first time.