92525-22-9

Basic information

• Product Name: 1H-Pyrazole-5-methanol, 1-methyl-a-propyl-
• CAS NO: 92525-22-9
• Molecular Formula: C8H14N2O
• Molecular Weight: 154.212
• Mol File: 92525-22-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazole-5-methanol, 1-methyl-a-propyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-5-methanol, 1-methyl-a-propyl-(92525-22-9)
• EPA Substance Registry System: 1H-Pyrazole-5-methanol, 1-methyl-a-propyl-(92525-22-9)

Safety Data

• Hazardous Substances Data: 92525-22-9(Hazardous Substances Data)

Upstream product

• 92524-99-7 1-methyl-5-(trimethylsilyl)-1H-pyrazole 
• 123-72-8 butyraldehyde 

Relevant articles and documents

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.