3463-26-1

Basic information

• Product Name: 1-Methyl-3-phenyl-pyrazole
• Synonyms: 1-Methyl-3-phenyl-pyrazole;1-Methyl-3-phenyl-1H-pyrazole
• CAS NO: 3463-26-1
• Molecular Formula: C₁₀H₁₀N₂
• Molecular Weight: 158
• Mol File: 3463-26-1.mol

Chemical Properties

• Melting Point: 56°C
• Boiling Point: 280.55°C
• Flash Point: 123.4°C
• Appearance: /
• Density: 1.0232
• Vapor Pressure: 0.00641mmHg at 25°C
• Refractive Index: 1.6057 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 1.72±0.10(Predicted)
• CAS DataBase Reference: 1-Methyl-3-phenyl-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-3-phenyl-pyrazole(3463-26-1)
• EPA Substance Registry System: 1-Methyl-3-phenyl-pyrazole(3463-26-1)

Safety Data

• Hazardous Substances Data: 3463-26-1(Hazardous Substances Data)

Usage

Uses

1-methyl-3-phenyl-pyrazole is used as a research reagent for the synthesis of bioactive important small molecules. Its expression is as follows:
Used in Pharmaceutical Industry:
1-methyl-3-phenyl-pyrazole is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those with potential therapeutic applications. Its unique structure allows for the development of new drugs with improved efficacy and selectivity.
Used in Chemical Research:
1-methyl-3-phenyl-pyrazole serves as a valuable research tool in the field of organic chemistry, enabling scientists to explore new reaction pathways and develop innovative synthetic methods. Its versatile structure makes it a promising candidate for the creation of novel chemical entities with diverse applications.
Used in Material Science:
1-methyl-3-phenyl-pyrazole may also find applications in the development of new materials with specific properties, such as those with enhanced conductivity, magnetism, or optical characteristics. Its unique structure can be exploited to design and synthesize advanced materials for various industrial applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 62, p. 8325, 1997 DOI: 10.1021/jo970897r

InChI:InChI=1/C10H10N2/c1-12-8-7-10(11-12)9-5-3-2-4-6-9/h2-8H,1H3

Upstream product

• 74-83-9 methyl bromide 
• 2458-26-6 3-phenylpyrazole 
• 77-78-1 dimethyl sulfate 
• 51772-25-9 1,2-dimethyl-3-phenyl-pyrazolium; iodide 
• 3506-51-2 Benzoyl acetaldehyde 
• 60-29-7 diethyl ether 
• 60-34-4 methylhydrazine 
• 57623-20-8 3-benzoyloxy-1-phenyl-propenone 
• 33603-87-1 β-chlorocinnamaldehyde 
• 3306-07-8 1-benzoyl-2-chloroethene 
• 105994-56-7 1-methyl-3-phenyl-1H-pyrazole-4-carboxylic acid 
• 304477-40-5 1-methyl-3-phenyl-1H-pyrazole-4-carbaldehyde 
• 74-88-4 methyl iodide 
• 1402242-69-6 potassium trifluoro(1-methyl-3-phenyl-1H-pyrazol-5-yl)borate 

Downstream Products

• 51772-25-9 1,2-dimethyl-3-phenyl-pyrazolium; iodide 
• 105994-55-6 4-bromo-1-methyl-3-phenyl-1H-pyrazole 
• 85302-22-3 (1-methyl-3-phenyl-1H-pyrazol-4-yl)phenylmethanone 
• 105994-77-2 4-bromo-1-methyl-5-phenyl-1H-pyrazole 
• 1345118-52-6 C₁₀H₁₁BN₂O₂ 
• 1361379-47-6 N-(2,6-difluorophenyl) [5-(1-methyl-3-phenylpyrazol-5-yl)(2-thienyl)]carboxamide 
• 1361379-74-9 C₂₀H₁₅FN₄OS 
• 1361380-63-3 C₁₃H₁₂N₄S 
• 63637-58-1 3-phenyl-1-(4-methylphenyl)-1H-pyrazole 
• 66129-68-8 1-Methyl-3-phenyl-1H-pyrazole-4-carbonyl chloride 
• 105994-56-7 1-methyl-3-phenyl-1H-pyrazole-4-carboxylic acid 

Relevant articles and documents

Cascade reaction to 1H-pyrazoles from hydrazones via sodium Ni-trite promoted dual C–C/C–N formation, annulation and aromatization with 1,2-dichloroethane

A novel route for tandem C–C/C–N formation, annulation and aromatization of hydrazones with 1,2-dichloroethane to synthesize 1H-pyrazoles has been developed. Furthermore, the 1,2-dichloroethane serves as alkylation reagent in good to excellent yields. This methodology features mild reaction conditions and good functional group tolerance, providing a direct approach for the preparation of 1H-pyrazoles.

Preparation method of pyrazole derivative (by machine translation)

The preparation method comprises the following steps: mixing an alkyne propyl alcohol derivative, a halogen source, an acid and a solvent, heating and reacting, and reacting to Meyer - Schuster generate the pyrazole derivative. Compared with the prior art, the preparation method disclosed by the invention has 91% the advantages of maximum yield, simple operation, mild conditions, high conversion rate, few byproducts and the like, and provides a brand-new synthetic method for construction of pyrazole compounds. (by machine translation)

Cu-promoted sydnone cycloadditions of alkynes: Scope and mechanism studies

Cu salts have been found to promote the cycloaddition reaction of sydnones and terminal alkynes, providing significant reduction in reaction times. Specifically, the use of Cu(OTf)2 is found to provide 1,3-disubstituted pyrazoles, whereas simpl

Copper-Catalyzed aerobic intramolecular dehydrogenative cyclization of n,n-disubstituted hydrazones through C sp 3 -H functionalization

An aerobic activity: The title reaction proceeds through an oxidation/cyclization/aromatization sequence under an atmosphere of O 2 (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene, DCE=1,2-dichloroethane, DMS=dimethylsulfide). This coupling

Synthesis of ynone trifluoroborates toward functionalized pyrazoles

The synthesis of a range of novel ynone trifluoroborates has been achieved, in a two-pot process from propargylic alcohols. These alkynes have been subsequently used in the formation of a range of pyrazole trifluoroborate salts via cyclization with hydrazines. The products are generated with high levels of regiocontrol and in excellent yields and represent versatile synthetic intermediates.

COMPOUNDS THAT MODULATE INTRACELLULAR CALCIUM

Described herein are compounds and pharmaceutical compositions containing such compounds, which modulate the activity of store-operated calcium (SOC) channels. Also described herein are methods of using such SOC channel modulators, alone and in combination with other compounds, for treating diseases or conditions that would benefit from inhibition of SOC channel activity.

IMIDAZOPYRIDAZINE COMPOUNDS

The present invention relates to novel substituted imidazo[1,2-b]pyridazine compounds of Formula (I): pharmaceutical compositions thereof, and the use such compounds as corticotropin releasing factor 1 (CRF1) receptor antagonists in the treatment of psychiatric disorders and neurological diseases.

Reactions of acetophenonmonomethyl- and -dimethylhydrazones with the Vilsmeier-Reagent; formation of pyrazol-4-carbiminium salts: A contribution to the mechanism

Kira discovered the formation of (4e) N,N-Dimethyl-N-[1,3-diphenylpyrazol-4-ylmethylen]ammonium perchlorat by the reaction from acetophenonphenylhydrazone 1e with the Vilsmeier-Reagent 2. On the example of the Acetophenonmonomethylhydrazone 1a we represen

Photochemistry of Phenyl-Substituted 1-Methylpyrazoles

Direct irradiation of 1-methyl-4-phenylpyrazole (2) in methanol results in regiospecific phototransposition to 1-methyl-4-phenylimidazole (4) and in photocleavage to (E)/(Z)-3-(N-methylamino)-2-phenylpropenenitrile (5) and (E)/(Z)-2-(N-methylaimno)-1-phenylethenyl isocyanide (6). Deuterium labeling confirms that the phototransposition occurs via the P4 permutation pathway. Separate experiments show that 5 and 6 undergo (Z) → (E) isomerization and photocyclization to imidazole 4. Quantum yields for these reactions show that the sequence 2 → 6 → 4 is a major pathway for the P4 phototransposition of 2 → 4. Isocyanides were also detected as intermediates in the P4 phototransposition of a variety of other pyrazoles confirming the generality of this pathway in pyrazole photochemistry. Direct irradiation of 1-methyl-5-phenylpyrazole (3) resulted in the formation of 1-methyl-5-phenylimidazole (7), 1-methyl-2-phenylimidazole (8), and 1-methyl-4-phenylimidazole (4). Deuterium labeling revealed that these products were formed by P4, P6, and P7 permutation pathways, respectively. (E)/(Z)-3-(N-methylamino)-3-phenylpropenenitrile (9) and (E)/(Z)-2-(N-methylamino)-2-phenylethenyl isocyanide (10) photocleavage products were also formed in this reaction. Irradiation of 3 in furan solvent did not result in phototransposition but led to the formation of endo and exo adducts formed by Diels-Alder reaction of furan with 4-phenyl-5-methyl-1,5-diazabicyclo[2.1.0]pent-2-ene. This constitutes the first direct evidence for the formation of a 1,5-diazabicyclo[2.1.0]hex-2-ene from photolysis of a pyrazole and is consistent with the electrocyclic ring closure - heteroatom migration mechanism suggested for the P6 and P7 phototranspositions.

The Reaction of 1,1-Dimethyl-1-Phenacylhydrazinium Bromide with Aqueous Sodium Hydroxide

The reaction of 1,1-dimethyl-1-phenacylhydrazinium bromide with 1 M aqueous sodium hydroxide give benzoic acid, 3-phenyl-1-methylpyrazole, 5-benzoyl-3-phenyl-1-methylpyrazole, and benzonitrile as the major components; the expected product, 2-benzoyl-5-phenylimidazole was formed in only small amounts.Mechanisms to rationalize the formation of the major products are discussed.