92524-99-7

Usage

Pyrazole derivative

A compound derived from the pyrazole structure, which is a five-membered heterocyclic ring containing two nitrogen atoms.

Methyl group

A chemical group consisting of one carbon atom bonded to three hydrogen atoms, attached to the nitrogen atom in the compound.

Trimethylsilyl group

A chemical group consisting of one silicon atom bonded to three methyl groups, also attached to the nitrogen atom in the compound.

Intermediate in synthesis

Commonly used as a starting material or building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds.

Potential biological activity

Possesses the ability to interact with biological systems, which may lead to potential applications in the development of novel drugs.

Unique properties from trimethylsilyl group

The presence of the trimethylsilyl group can impart special characteristics to the molecule, making it useful in various research and industrial applications.

Diverse potential uses

1-METHYL-5-TRIMETHYLSILANYL-1H-PYRAZOLE has potential applications in the fields of medicine, agriculture, and materials science.

Upstream product

• 930-36-9 1-methyl-1H-pyrazole 
• 75-77-4 chloro-trimethyl-silane 
• 24602-40-2 trimethyl(1H-pyrazol-3-yl)silane 
• 74-88-4 methyl iodide 

Downstream Products

• 61496-24-0 (1-methyl-1H-pyrazol-5-yl)(phenyl)methanone 
• 92525-23-0 5-<4-chlorophenyl-(trimethylsiloxy)methyl>-1-methylpyrazole 
• 930-36-9 1-methyl-1H-pyrazole 
• 92525-22-9 5-(1-hydroxybutyl)-1-methylpyrazole 
• 92525-24-1 5-<<4-(dimethylamino)phenyl>-(trimethylsiloxy)methyl>-pyrazole 
• 92525-25-2 1-methyl-5-<1-phenyl-1-(trimethylsiloxy)ethyl>-pyrazole 
• 92525-26-3 1-methyl-5-<(E)-3-phenyl-1-(trimethylsiloxy)-2-propenyl>-1-methylpyrazole 
• 92525-27-4 5-<(E)-1,3-diphenyl-1-(trimethylsiloxy)-2-propenyl>-1-methylpyrazole 
• 92525-14-9 1-methyl-5--pyrazole 
• 92525-17-2 1-methyl-5-(4-toluenesulfonyl)pyrazole 
• 92525-29-6 1,N,N-trimethylpyrazole-5-carboxyamide 

Relevant academic research and scientific papers

Access to Silylated Pyrazole Derivatives by Palladium-Catalyzed C?H Activation of a TMS group

A simple and efficient approach to new silylated heterocycles of potential interest in medicinal chemistry is presented. A set of bromophenyl trimethylsilyl pyrazole intermediates can be transformed by direct organometallic routes into two families of regioisomeric iodoaryl substrates; using either arylzinc or aryllithium chemistry, the TMS group remains on the pyrazole ring or translocates to the aryl moiety. These two families can then be efficiently transformed into benzo silino pyrazoles thanks to a single-step cyclization relying on the Pd-catalyzed activation of a non-activated C(sp3)?H bond alpha to a silicon atom. The experimental conditions used, which are fully compatible with the pyrazole ring, suggest that this reaction evolves through a concerted metalation–deprotonation (CMD) mechanism.

Regioselective Halo- and Carbodesilylation of (Trimethylsilyl)-1-methylpyrazoles

The isomeric 3-, 4-, and 5-(trimethylsilyl)- as well as the 3,4-, 3,5-, and 4,5-bis(trimethylsilyl)-1-methylpyrazoles (2, 7, 3, 5, 9, and 10, respectively) are obtained by methylation of the corresponding (trimethylsilyl)-1H-pyrazoles or by silylation of Grignard or lithio derivatives of appropriate 1-methylpyrazoles with chlorotrimethylsilane. 5 and 10 are halodesilylated regioselectively by Br2 or ICl in the 4-position, yielding 13 and 15.With addditional bromine, these monobromo compounds suffer exclusively bromodesilylation to give 3,4- and 4,5-dibromo-1-methylpyrazole (14 and 16, respectively).These findings are in accord with the electrophilic substitution reactivity indices for 1-methylpyrazole (8) and with ipso-directing influence of the Me3Si group.The reaction of 5 with I2, unexpectedly, attacks preferentially at the 3-position.Regioselective carbodesilylation in the 5-position is observed in the fluoride-catalyzed reactions of 3, 9, and 10 with carbon electrophiles.The high regiospecificity of this reaction is rationalized in terms of carbanion stabilization at the individual pyrazole positions.