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
• Article Data: 5

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 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 102402-84-6 3-(adamantan-1-yl)pentane-2,4-dione 

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.

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.