18742-02-4

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(2-Bromoethyl)-1,3-dioxolane is used as a pharmaceutical intermediate for the synthesis of various drugs, including EGFR inhibitors and orally active agents targeting cancer and cell proliferation with quinoline substructures. It plays a crucial role in the development of novel therapeutics for cancer treatment.
Used in Chemical Synthesis:
As an alkylating agent, 2-(2-Bromoethyl)-1,3-dioxolane is used for amines, 1,3-dithianes, and carboximides. It is also utilized in the synthesis of aldehydes via the Grignard reagent, showcasing its versatility in organic chemistry.
Used in Flavoring Industry:
2-(2-Bromoethyl)-1,3-dioxolane is employed as a flavoring agent, contributing to the development of new and innovative flavors in the food and beverage industry.
Used in Organic Building Blocks:
2-(2-Bromoethyl)-1,3-dioxolane serves as a valuable organic building block in the synthesis of dioxolanes, acetals, and ketals, which are essential components in various chemical and pharmaceutical applications.
Used in Copper-Catalyzed Borylation:
In the field of chemical research, 2-(2-Bromoethyl)-1,3-dioxolane is used in copper-catalyzed borylation reactions with bis(pinacolato)diboron, followed by treatment with potassium bifluoride to afford key organotrifluoroborate reagents, which are essential for further chemical transformations and synthesis.

Purification Methods

Dissolve it in pentane, wash with 5% aqueous NaHCO3, dry (Na2SO4), and evaporate. Distil the residue. [NMR: Büchi & Wüest J Org Chem 34 1122 1969, Kriesat & Gisvold J Pharm Sci 60 1250 1971, Beilstein 19/1 V 69.]

InChI:InChI=1/C6H11BrO2/c7-3-2-6-8-4-1-5-9-6/h6H,1-5H2

Upstream product

• 3984-22-3 2-vinyl-1,3-dioxolane 
• 107-21-1 ethylene glycol 
• 107-02-8 acrolein 
• 65032-54-4 3-bromopropanal 

Downstream Products

• 70738-50-0 2-methoxy-5-(p-methoxybenzyl)-5-(p-methoxyphenyl)tetrahydrofuran 
• 81574-79-0 (E)-1,1-ethylenedioxy-4,5-bis-(p-methoxyphenyl)pent-4-ene 
• 29329-26-8 2,2-dimethyl-2-nitro-1-phenyl-1-ethanone 
• 113304-48-6 1-(2-[1,3]Dioxolan-2-yl-ethyl)-cyclohex-2-enol 
• 70147-63-6 3-<2-(1,3-dioxolan-2-yl)ethyl>cyclohexanone 
• 78309-66-7 2-[2-(2-Methyl-cyclohexa-1,5-dienyl)-ethyl]-[1,3]dioxolane 
• 70738-49-7 1,1-ethylenedioxy-4-hydroxy-4,5-bis-(p-methoxyphenyl)pentane 
• 70147-64-7 3-methyl-3-<2-(1,3-dioxolan-2-yl)ethyl>cyclohexanone 
• 69803-56-1 1-(diphenylphosphinoyl)-2-(1,3-dioxolan-2-yl)ethane 
• 121196-21-2 2-<2-(1,3-dioxolan-2-yl)ethyl>cyclohexanone N,N-dimethylhydrazone 
• 144648-12-4 5,5-dimethyl-3-<2-(1,3-dioxolan-2-yl)-ethyl>-2-cyclohexen-1-one 
• 120447-87-2 2-<3-(Phenylsulfonyl)propyl>-1,3-dioxolane 
• 100157-43-5 4-[1,3]Dioxolan-2-yl-2,2-diphenyl-butyronitrile 
• 155528-97-5 2-[2-(2-Methoxy-cyclohexa-2,5-dienyl)-ethyl]-[1,3]dioxolane 

Relevant academic research and scientific papers

Discovery of a novel class of inhaled dual pharmacology muscarinic antagonist and β2 agonist (MABA) for the treatment of chronic obstructive pulmonary disease (COPD)

The targeting of both the muscarinic and β-adrenergic pathways is a well validated therapeutic approach for the treatment of chronic obstructive pulmonary disease (COPD). In this communication we report our effort to incorporate two pharmacologies into a single chemical entity, whose characteristic must be suitable for a once daily inhaled administration. Contextually, we aimed at a locally acting therapy with limited systemic absorption to minimize side effects. Our lung-tailored design of bifunctional compounds that combine the muscarinic and β-adrenergic pharmacologies by the elaboration of the muscarinic inhibitor 7, successfully led to the potent, pharmacologically balanced muscarinic antagonist and β2 agonist (MABA) 13.

Preparation and properties of a novel solution of hydrogen bromide (HBr) in 1,4-dioxane: An alternative reagent to HBr gas without protic solvents

A solution of hydrogen bromide (HBr) in 1,4-dioxane was prepared and investigated for its ability to brominate alcohols, and hydrobrominate alkenes. This study revealed that the brominating ability of this HBr/1,4-dioxane solution is equal or superior to that of hydrobromic acid or HBr in acetic acid. The solution of HBr in 1,4-dioxane is robust, exhibiting no decomposition of the solvent, and retaining 97% of its original concentration, when kept at ?25 °C for 30 days. This solution is a liquid alternative to HBr gas without protic solvents.

METHOD FOR PRODUCING BROMINE-CONTAINING CYCLIC ACETAL COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing a bromine-containing cyclic acetal compound with high efficiency and high yields and, additionally, provide a highly safe and inexpensive production method. SOLUTION: A bromine-containing cyclic acetal compound is obtained with high yields by the reaction of an α,β-unsaturated carbonyl compound, hydrogen bromide and ethylene glycol in coexistence of ether. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Concise catalytic asymmetric total synthesis of biologically active tropane alkaloids

A general strategy for the total asymmetric synthesis of valuable tropane alkaloids by catalytic stereoselective transformations is disclosed. The power of this approach is exemplified by the concise catalytic enantioselective total syntheses of (+)-methylecgonine, (-)-cocaine and (+)-cocaine as well as the first catalytic asymmetric total syntheses of a cocaine C-1 derivative and (+)-ferruginine starting from 5-oxo-protected-α,β-unsaturated enals using only two and three column chromatographic purification steps, respectively. Copyright

AN IMPROVED SYNTHESIS OF 2-(β-BROMOETHYL)-2-METHYL-1,3-DIOXOLANE, A USEFUL METHYL VINYL KETONE EQUIVALENT

A general method for the formation of β-bromo-ketals, and its application to an improved synthesis of 2-(β-bromoethyl)-2-methyl-1,3-dioxolane, a useful methyl vinyl ketone equivalent, in 82percent yield, are described.

INTRAMOLECULAR DIELS-ALDER REACTION OF THIOALDEHYDES

Intramolecular Diels-Alder reaction of thioaldehydes which were generated from bis(trimethylsilyl)sulfide and dienals gave the corresponding bicyclic adducts.

TRIMETHYLSILYL-HALIDE-MEDIATED CONJUGATED ADDITION TO ALLYLIC ACETALS

Trimethylsilyl chloride can effect the conjugated addition of NaX (X=Br, I, SCN) to α,β-unsaturated acetals and ketals without deprotection of the carbonyl group.