108221-12-1

Basic information

• Product Name: 4-(1-adamantyl)-3,5-dimethyl-1H-pyrazole
• Synonyms: 4-(1-adamantyl)-3,5-dimethyl-1H-pyrazole
• CAS NO: 108221-12-1
• Molecular Formula: C15H22N2
• Molecular Weight: 230.34858
• Mol File: 108221-12-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(1-adamantyl)-3,5-dimethyl-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1-adamantyl)-3,5-dimethyl-1H-pyrazole(108221-12-1)
• EPA Substance Registry System: 4-(1-adamantyl)-3,5-dimethyl-1H-pyrazole(108221-12-1)

Safety Data

• Hazardous Substances Data: 108221-12-1(Hazardous Substances Data)

Upstream product

• 768-90-1 1-Adamantyl bromide 
• 32314-61-7 1-nitroxyadamantane 
• 102402-84-6 3-(adamantan-1-yl)pentane-2,4-dione 
• 67-51-6 3,5-dimethyl-1H-pyrazole 

Relevant articles and documents

Regioselective adamantylation of N-unsubstituted pyrazole derivatives

Reaction of NH-pyrazoles with 1-bromoadamantane in a high pressure stainless steel autoclave (250 ml, maximum working pressure of 200 atm) gives regioselectively 1-adamantyl or 4-adamantylpyrazoles depending on the temperature.

Synthesis of azolyl-substituted adamantane derivatives and their coordination compounds

Reactions of adamantylazoles with nucleophiles (water, carbon monoxide, acetonitrile) in sulfuric acid were studied. New bifunctional adamantane derivatives containing one heterocyclic substituent and one hydroxyl or acetamide substituent were synthesized. The coordination compounds of copper(II) and zinc(II) with 1-adamantyl-1,2,4-triazole, 4-adamantylpyrazole, and 4-adamantyl-3,5-dimethylpyrazole were synthesized and structurally characterized. These complexes are first examples of coordination compounds of azolyladamantanes.

ADAMANTYLATION OF N-UNSUBSTITUTED PYRAZOLE DERIVATIVES: MECHANISTIC AND STRUCTURAL STUDIES

Reaction of NH-pyrazoles with 1-bromoadamantane in a high pressure stainless steel autoclave gives regioselectively 1-(1-adamantyl)- or 4-(1-adamantyl)pyrazoles depending on the temperature.A series of cross-experiments allows to establish the mechanism of this reaction.The molecular structure of the most simple derivative, 4-(1-adamantyl) pyrazole (3a), has been determined.Intramolecular N-H...N hydrogen bonds hold the four independent molecules together in a helix system parallel to the c axis.The crystal is built up of two centrosymmetrically related helices.

METAL COMPLEXES IN ORGANIC SYNTHESIS. PREPARATION OF α-(1-ADAMANTYL)-β-DICARBONYL COMPOUNDS AND 4-(1-ADAMANTYL)-3,5-DISUBSTITUTED PYRAZOLES AND ISOXAZOLES.

α-(1-adamantyl)-β-dicarbonyl compounds are prepared by the reactions of the Co(II) complexes of β-dicarbonyl compounds with 1-bromoadamantane.This provides a route to the previously inaccessible 4-(1-adamantyl)-3,5-disubstituted pyrazoles and isoxazoles.