7314-84-3

Basic information

• Product Name: 2,2-Dibromoadamantane
• Synonyms: 2,2-Dibromoadamantane
• CAS NO: 7314-84-3
• Molecular Formula: C10H14Br2
• Molecular Weight: 294.03
• Mol File: 7314-84-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-Dibromoadamantane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dibromoadamantane(7314-84-3)
• EPA Substance Registry System: 2,2-Dibromoadamantane(7314-84-3)

Safety Data

• Hazardous Substances Data: 7314-84-3(Hazardous Substances Data)

Usage

Molecular weight

291.03 g/mol

Structure

A bromine atom attached to each of the carbons at the 2-position of an adamantane skeleton.

Physical form

Colorless crystalline solid.

Melting point

High melting point.

Solubility

Insoluble in water, soluble in organic solvents.

Uses

Commonly used as a building block in organic synthesis, particularly in the preparation of pharmaceuticals and agrochemicals.

Applications

Potential applications in materials science and polymer chemistry due to its unique molecular structure.

Properties

Possesses interesting chemical and physical properties that make it a valuable reagent in research and industrial processes.

Upstream product

• 700-58-3 2-Adamantanone 
• 41736-95-2 spiro[adamantane-2,3'-diazirine] 

Downstream Products

• 39646-72-5 (Z)-1,4-dibromoadamatane 

Relevant articles and documents

The Hydrogen-Bond Basicity pKHB Scale of Peroxides and Ethers

Using 4-fluorophenol as a reference hydrogen-bond donor, equilibrium constants, Kf, for the formation of 1:1 hydrogen-bonded complexes have been obtained by FTIR spectrometry for 39 ethers of widely different structure (cyclic and acyclic ethers, crown ethers, glymes, acetals, orthoesters, and disiloxane) and 3 peroxides, in CCl4 at 298 K. The pkHB scale of monoethers extends from 1.44 for 2,3-diadamant-2-yloxirane to -0.53 for hexamethyldisiloxane. The main effects explaining the variation of the hydrogen-bond basicity of sp3 oxygen atoms are (i) the electron-withdrawing field-inductive effect [e.g. in (CF3)2CHOMe], (ii) the electron-withdrawing resonance effect (e.g. in EtOCH=CH2) (iii) the steric effect (e.g. in tBu2O), (iv) the lone-pair-lone-pair repulsion (e.g. in cyclic peroxides), and (v) the cyclization giving the basicity order: oxetane > tetrahydrofuran > tetrahydropyran > oxirane. A spectroscopic scale of hydrogen-bond basicity is constructed from, the infrared frequency shift Δv(OH) of methanol hydrogen-bonded to peroxides and ethers. The thermodynamic pKHB scale does not correlate with the Δv(OH) scale because of (i) statistical effects in polyethers and peroxides (ii) secondary hydrogen-bond acceptor sites (e.g. in benzyl ether), (iii) variations of the s character of oxygen lone pairs either by conjugation or cyclization, (iv) steric effects, (v) lone-pair-lone-pair repulsions, and (vi) anomeric effects. The v(OH...O) band shape reveals two stereoisomeric complexes, the most stable being tetrahedral at the ether oxygen atom.

Semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and -2-ol

A number of new polybrominated adamantanes were formed by rearrangements and bromination of 2,2,6,6-tetrabromoadamantane under Friedel-Crafts conditions. Protoadamantane-4,10-dione, 10-acetoxyprotoadamantan-4-one, 1,2,6-triacetoxyadamantane and 5,6-diacetoxyadamantan-2-one were formed by successive semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and 5,6-dibromoadamantan-2-ol. This work may open up new pathways for the synthesis of 1,2,6-trisubstituted adamantanes.