23705-85-3

Basic information

• Product Name: Dimethyl 4-Hydroxypyrazole-3,5-dicarboxylate
• Synonyms: Dimethyl 4-Hydroxypyrazole-3,5-dicarboxylate
• CAS NO: 23705-85-3
• Molecular Formula: C₇H₈N₂O₅
• Molecular Weight: 200.14882
• Mol File: 23705-85-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 329.0±37.0 °C(Predicted)
• Appearance: /
• Density: 1.480±0.06 g/cm3(Predicted)
• PKA: 8.66±0.20(Predicted)
• CAS DataBase Reference: Dimethyl 4-Hydroxypyrazole-3,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 4-Hydroxypyrazole-3,5-dicarboxylate(23705-85-3)
• EPA Substance Registry System: Dimethyl 4-Hydroxypyrazole-3,5-dicarboxylate(23705-85-3)

Safety Data

• Hazardous Substances Data: 23705-85-3(Hazardous Substances Data)

Usage

General Description

Dimethyl 4-hydroxypyrazole-3,5-dicarboxylate is a chemical compound that belongs to the class of pyrazole derivatives. It is commonly used in the pharmaceutical industry as a building block for the synthesis of various drugs and pharmaceutical compounds. This chemical is known for its potent antioxidant properties and is often added to skincare products and cosmetics to protect the skin from oxidative damage. Additionally, it is also widely used in the manufacturing of agrochemicals and other industrial applications. Its unique structure and properties make it a valuable and versatile compound in various fields of science and industry.

Upstream product

• 83878-89-1 2-diazo-3-oxo-pentanedioic acid dimethyl ester 
• 6773-29-1 dimethyl diazomalonate 
• 108-59-8 malonic acid dimethyl ester 
• 623-73-4 diazoacetic acid ethyl ester 
• 105-53-3 diethyl malonate 
• 18424-76-5 dimethyl malonate sodium salt 
• 622-37-7 Phenyl azide 

Downstream Products

• 74-87-3 methylene chloride 
• 15719-64-9 methylammonium carbonate 
• 4843-98-5 4-hydroxy-pyrazole 
• 933984-70-4 dimethyl 4-(benzyloxy)-1H-pyrazole-3,5-dicarboxylate 

Relevant articles and documents

Identification of the C-Glycoside Synthases during Biosynthesis of the Pyrazole-C-Nucleosides Formycin and Pyrazofurin

C-Nucleosides are characterized by a C?C rather than a C?N linkage between the heterocyclic base and the ribofuranose ring. While the biosynthesis of pseudouridine-C-nucleosides has been studied, less is known about the pyrazole-C-nucleosides such as the formycins and pyrazofurin. Herein, genome screening of Streptomyces candidus NRRL 3601 led to the discovery of the pyrazofurin biosynthetic gene cluster pyf. In vitro characterization of gene product PyfQ demonstrated that it is able to catalyze formation of the C-glycoside carboxyhydroxypyrazole ribonucleotide (CHPR) from 4-hydroxy-1H-pyrazole-3,5-dicarboxylic acid and phosphoribosyl pyrophosphate (PRPP). Similarly, ForT, the PyfQ homologue in the formycin pathway, can catalyze the coupling of 4-amino-1H-pyrazole-3,5-dicarboxylic acid and PRPP to form carboxyaminopyrazole ribonucleotide. Finally, PyfP and PyfT are shown to catalyze amidation of CHPR to pyrazofurin 5′-phosphate thereby establishing the latter stages of both pyrazofurin and formycin biosynthesis.

Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: Experimental and computational study

Non-fluorinated vinyldiazo compounds with trans-configuration irrespective of the nature of 3-R1-substituent (R1 = H, Me, TBSO) even under ambient conditions easily cyclize to produce pyrazoles, while cis-stereoisomers undergo similar ring closure only at elevated temperatures or decompose to produce vinyloxocarbene reaction products. The 3-CF 3-substituted analogues with cis- or trans-configuration do not produce pyrazoles at all, but on heating furnish only vinylcarbene derived products. DFT calculations of theoretical energy barriers adequately explain the different experimental reactivity found for stereoisomeric vinyldiazocarbonyl compounds, and a new model for their interconversion through the corresponding pyrazoles has been suggested. The Royal Society of Chemistry.