35845-64-8

Usage

Uses

(2-BROMOETHYL)BENZENE-D5 is an intermediate widely used in organic synthesis.

Upstream product

• 35845-63-7 [phenyl-2H₅]phenylethyl alcohol 
• 84783-81-3 phenylmagnesium bromide-d5 
• 4165-57-5 bromobenzene-d5 

Downstream Products

• 72023-97-3 C₁₅H₁₁⁽²⁾H₅O₂ 
• 35845-62-6 the d5-phenyl ring labelled 3-phenylpropanoic acid 

Relevant academic research and scientific papers

The synthesis of [phenyl-2H5]gluconasturtiin and its metabolites for metabolic studies

The synthesis of a deuterium labelled glucosinolate, [2H 5]gluconasturtiin, is described starting from [2H 5]bromobenzene. The potential metabolites of the glucosinolate, namely the [phenyl-2H5/

On the Generation and Characterization of the Spirooctadienyl Anion in the Gas Phase

Three routes have been explored in both a high-pressure chemical ionization (CI) source and a low-pressure Fourier transform ion cyclotron resonance (FT-ICR) cell to generate the spirooctadienyl anion in the gas phase: (i) proton abstraction from spiroocta-4,6-diene; (ii) expulsion of trimethylsilyl fluoride by phenyl ring participation following fluoride anion attack upon the silicon centre of 2-phenylethyl trimethylsilane; and (iii) collisionally induced dissociation (CID) of the carboxylate anion of 3-phenylpropanoic acid via carbon dioxide loss.From comparison of the CID spectra of various reference (1-) ions with those of the (1-) ions with those of the (1-) ions which could be generated via the routes (i) and (iii) in the CI source it can be concluded that only the third route yields a (1-) in whose CID spectrum is not inconsistent with the one expected for the spirooctadienyl anion.In the FT-ICR cell (1-) ions are generated along all three routes; their structures have been identified by specific ion-molecule reactions and appear to be different.Route (i) yields an α-methyl benzyl anion, probably due to isomerization within the ion-molecule complex formed.An ortho-ethylphenyl anions is formed along route (ii), presumably due to an intramolecular ortho proton abstraction in the generated trimethylsilyl fluoride solvated 2-phenylethyl primary carbanion.The (1-) ion formed along route (iii) shows reactions similar to those of the 1,1-dimethylcyclohexadienyl anion which is structurally related to the spirooctadienyl anion.Furthermore, the (1-) ion generated via route (iii) reacts with hexafluorobenzene under expulsion of only one hydrogen fluoride molecule which contains exclusively one of the original phenyl ring hydrogen atoms.On the basis of all these observations it is therefore quite likely that the spirooctadienyl anion is formed by collisionally induced decarboxylation of the 3-phenylpropanoic acid carboxylate anion and can be a long-lived and stable species in the gas phase.

INTRAMOLECULAR RING-TO-RING PROTON TRANSFER IN GASEOUS ( omega -PHENYLALKYL)BENZENIUM IONS.

Gaseous (2-phenylethyl)benzenium and (3-phenylpropyl)benzenium ions are generated easily by mass spectrometric loss of CO//2H from the positive molecular ions of the corresponding 1-( omega -phenylalkyl)-1,4-dihydrobenzoic acids. The major secondary fragm