53409-18-0

Upstream product

• 68430-08-0 2-(1-benzyl-4-methyl-1H-pyrazol-3-yloxy)-2-methyl-propionic acid 
• 145324-72-7 2-benzyl-4-methylpyrazole 1-oxide 

Downstream Products

• 79-41-4 poly(methacrylic acid) 
• 594-61-6 2-methyllactic acid 
• 594-58-1 2-chloro-2-methylpropanoic acid 
• 68430-08-0 2-(1-benzyl-4-methyl-1H-pyrazol-3-yloxy)-2-methyl-propionic acid 
• 212190-95-9 2-(1-Benzyl-4-methyl-1H-pyrazol-3-yloxy)-2-methyl-butyric acid 
• 111789-91-4 (1-Benzyl-4-bromo-4-methyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yloxy)-acetic acid 
• 111789-99-2 (1-Benzyl-4-methyl-1H-pyrazol-3-yloxy)-acetic acid 

Relevant academic research and scientific papers

LINK synthesis with 3-hydroxy-1H-pyrazoles: 3-carboxyisoalkyloxy-1H-pyrazoles-bicyclic acylpyrazolium salts and γ-lactams-3-carboxyisoalkyloxy-4,5-dihydro-1H-pyrazol-5-ones

1-Substituted 3-hydroxy-1H-pyrazoles 1 react with chloroform, NaOH, and aceton resp. butan-2-one O-regiospecifically to yield 2-methyl-2-[(1H-pyrazol-3-yl)oxy]-propanoic resp. -butanoic acids 14 via a dichlorocarbene (12)-dichlorooxirane (9) pathway. Chlorides 17 of 14 easily cyclize to N-acylpyrazolium salts 18/19, which quantitatively afford esters 22-26 and amides 27-29 of 14. Enantiomers of the butanoic acid 14h, obtained via their diastereomeric cholesterol esters, differ in their stimulus to peroxisome proliferation. At 140°C pyrazolium salts 18 undergo thermolysis to bicyclic β-oxa-γ-lactams 30-32. 3-Carboxyisoalkylamino-pyrazoles similarly give 1H-β-aza-γ-lactams 34. Reactions of 14 with surplus SOCl2 result in 6-chloro-37 resp. 7-chloro-β-oxa-γ-lactams 38 via chlorosulfinylation and extrusion of SO, and in 4,4-bispyrazolyl-sulfoxide 39. A mild introduction of additional O-functions into pyrazoles affording 4,5-dihydro-3-hydroxy-5-oxo-1H-pyrazoles 52-57 is presented. Biological effects of the new pyrazoles are protection against shock and ADP-induced thromboembolism, reduction of serum lipids and improvement of blood flow. Johann Ambrosius Barth 1998.

Activation of Exocyclic α-Positions of Azole N-Oxides by O-Silylation

Exocyclic α-positions at immonium ring carbon atoms of pyrazole and 1,2,3-triazole 1-oxides are selectively attacked in a one-pot sequence comprising silylation with iodotrimethylsilane, deprotonation with 1,2,2,6,6-pentamethylpiperidine and allylic substitution of the trimethylsilyloxy group with the iodide ions liberated by the silylation.In this way 3- and 5-iodomethylpyrazoles as well as 4-iodomethyl-1,2,3-triazoles are obtained in good yields.These may be useful for the preparation of heteroarylmethyl derivatives since the iodine atom can be displaced by even weak nucleophiles such as acetate ions.The side chain iodination is complementary to O-alkylation of the N-oxides followed by nucleophilic attack which preferentially takes place at ring carbon atoms.