84396-62-3

Basic information

• Product Name: 4-(tricyclo[3.3.1.1~3,7~]dec-1-yl)-1H-pyrazole
• Synonyms: 1H-pyrazole, 4-tricyclo[3.3.1.1~3,7~]dec-1-yl-; 4-(Adamantan-1-yl)-1H-pyrazole
• CAS NO: 84396-62-3
• Molecular Formula: C₁₃H₁₈N₂
• Molecular Weight: 202.2954
• Mol File: 84396-62-3.mol

Chemical Properties

• Boiling Point: 365.1°C at 760 mmHg
• Flash Point: 165.6°C
• Density: 1.19g/cm³
• Vapor Pressure: 3.37E-05mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: 4-(tricyclo[3.3.1.1~3,7~]dec-1-yl)-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(tricyclo[3.3.1.1~3,7~]dec-1-yl)-1H-pyrazole(84396-62-3)
• EPA Substance Registry System: 4-(tricyclo[3.3.1.1~3,7~]dec-1-yl)-1H-pyrazole(84396-62-3)

Safety Data

• Hazardous Substances Data: 84396-62-3(Hazardous Substances Data)

Upstream product

• 52086-98-3 1-Adamantylmalonaldehyd 
• 288-13-1 NH-pyrazole 
• 768-90-1 1-Adamantyl bromide 
• 288-88-0 1,2,4-Triazole 
• 281-23-2 adamantane 

Relevant articles and documents

SIMILARITY IN PHYSICAL ORGANIC CHEMISTRY: SUBSTITUENT EFFECTS ON THE INTRINSIC BASICITY OF 4-SUBSTITUTED PYRAZOLES

The gas-phase basicities of eight pyrazoles substituted only at position 4 (R4 = H, NO2, F, Cl, CO2C2H5, CH3, NH2, 1-adamantyl) were measured by Fourier transform ion cyclotron resonance.The experimental values were treated in two ways, first by comparing these values with the AM1-calculated proton affinities.Since the correlation was reasonably good , a set of 17 further 4-substituted pyrazoles and their cations were calculated using the AM1 approximation and their gas-phase basicities were estimated.Second, both the experimental and the AM1-calculated values were considered within the framework of the Taft-Topsom analysis of substituent effects.Comparison of the analyses for pyrazoles and pyridines led to the unexpected result that, in spite of differences in ring size and number of heteroatoms, both systems behave remarkably alike.

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.

Solvent-free and direct C(sp3)-H amination of adamantanes by grinding

A facile, direct and environmentally benign conversion of C(sp 3)-H bonds to C(sp3)-N bonds using substoichiometric amount of aprotic superelectrophiles polyhalomethane-AlX3 has been achieved by grinding under solvent-free

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.

Syntheses with Aliphatic Dialdehydes, XXXV. Syntheses with 1- and 2-Adamantyl Malonaldehyde

The reaction of 1- (1) and 2-adamantyl malonaldehyde (2) with suitable electrophiles and nucleophiles yields adamantyl-substituted open-chain (3-5), carbocyclic (6) as well as heterocyclic compounds (7-19) with peculiar properties due to the presence of the lipophilic adamantyl group.The tetrazolopyrimidine (16) exhibits a solvent-dependent tetrazolo-azido valence isomerization reaction. - Key words: Adamantane-1-yl and Adamantane-2-yl Substituted Carbo- and Heterocycles, Tetrazole-Azido Valence Isomerization, Tetrazolopyrimidine