201008-71-1

Basic information

• Product Name: 3,5-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE
• Synonyms: 1H-Pyrazole-4-carboxaldehyde, 3,5-dimethyl- (9CI);3,5-dimethyl-1H-pyrazole-4-carbaldehyde(SALTDATA: FREE);3,5-DiMethyl-1H-pyrazole-4-carboxaldehyde
• CAS NO: 201008-71-1
• Molecular Formula: C6H8N2O
• Molecular Weight: 124.14052
• Product Categories: ALDEHYDE;Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Nucleotides
• Mol File: 201008-71-1.mol

Chemical Properties

• Melting Point: 112 °C(Solv: benzene (71-43-2))
• Boiling Point: 299.4°C at 760 mmHg
• Flash Point: 139.3°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 0.00119mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: -20°C Freezer
• PKA: 12.77±0.50(Predicted)
• CAS DataBase Reference: 3,5-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE(201008-71-1)
• EPA Substance Registry System: 3,5-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE(201008-71-1)

Safety Data

• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 201008-71-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,5-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds, specifically piperazinyl benzimidazoles. These compounds serve as antagonists of the gonadotropin-releasing hormone receptor, which can be utilized in the treatment of conditions related to hormonal imbalances or reproductive disorders.
Used in Chemical Synthesis:
As a colorless oil, 3,5-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE can also be employed in the chemical synthesis of other organic compounds, potentially for various applications across different industries, such as agriculture, materials science, or specialty chemicals. Its aldehyde functional group allows for further reactions and modifications to create a diverse range of products.

InChI:InChI=1/C6H8N2O/c1-4-6(3-9)5(2)8-7-4/h3H,1-2H3,(H,7,8)

Upstream product

• 3398-16-1 4-Bromo-3,5-dimethylpyrazole 
• 949020-61-5 β-(4-formyl-3,5-dimethyl-1H-pyrazol-1-yl)propionic acid 
• 55727-23-6 3‐(1,3-dithiane-2-yl)pentane-2,4-dione 
• 123-54-6 acetylacetone 
• 100596-16-5 3-(1,3-dithian-2-yl)-pentane-2,4-dione 
• 4819-19-6 methyl β-(3,5-dimethyl-1H-pyrazol-1-yl)propionate 
• 949020-60-4 methyl β-(4-formyl-3,5-dimethyl-1H-pyrazol-1-yl)propionate 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 201008-65-3 3,5-dimethyl-4-(1,3-dithian-2-yl)-1H-pyrazole 

Downstream Products

• 890626-07-0 3,5-dimethyl-1-(1-methylethyl)-1H-pyrazole-4-carbaldehyde 
• 874278-18-9 C₂₇H₃₄N₆ 

Relevant articles and documents

Vilsmeier-Haak formylation of 3,5-dimethylpyrazoles

Formylation of N-alkyl-3,5-dimethyl-1H-pyrazoles according to Vilsmeier-Haak led to the formation of the corresponding 4-formyl derivatives. 3,5-Dimethyl-1H-pyrazole having no substituent on the nitrogen atom failed to undergo formylation at the 4 position under analogous conditions. 3,5-Dimethyl-1H-pyrazole-4-carbaldehyde was synthesized by alkaline hydrolysis of methyl β-(4-formyl-3,5-dimethyl-1H-pyrazol-1-yl)propionate and subsequent heating of the acid thus formed.

Preparation method of nitrogen unsubstituted-4-formyl pyrazole

The invention relates to a preparation method of nitrogen unsubstituted-4-formyl pyrazole. The preparation method comprises the following steps: taking 4-halogenated pyrazole or a 4-halogenated pyrazole derivative as a raw material; under the action of trifluoroacetic acid, carrying out reaction with 3, 4-dihydro-2H-pyrane to generate 4-halogenated-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole; carrying out lithiation reaction of 4-halogenated-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole and n-butyllithium at a low temperature, adding N, N-dialkyl formamide and other formylation reagents to introduceformyl, hydrolyzing in an acidic aqueous solution to remove protecting groups, and purifying to obtain the nitrogen unsubstituted-4-formyl pyrazole. The nitrogen unsubstituted-4-formyl pyrazole prepared by the preparation method disclosed by the invention is good in biological activity and has wide application in the fields of medicines and pesticides.

Routes to building blocks for heterocyclic synthesis by reduction of ketene dithioacetals

Two general methods have been developed permitting the effective reduction of ketene dithioacetals to give substituted dithianes. Reduction with magnesium in methanol is less reliable than reduction with zinc in acetic acid. The greater inconsistency of magnesium in methanol has been investigated by a cyclic voltammetric study of the substrates. The utility of the dithianes has been successfully illustrated by cyclisations to afford, after deprotection, a variety of heterocyclic aldehydes.