18742-02-4

Basic information

• Product Name: 2-(2-Bromoethyl)-1,3-dioxolane
• Synonyms: 2-(2-Bromoethyl)-1,3-dioxolane,3-Bromopropionaldehyde ethylene acetal;2-(2-Bromoethyl)-1,3;2-(2-BroMoethyl)-1,3-dioxolane, 97% 10GR;2-(2-BroMoethyl)-1,3-dioxolane 96%;2-(2-Bromoethyl)-1,3-dioxolane, 95%, stabilized;2- (2-Bromoethyl)-1,3-dioxolane, Stabilized with silver;2-(2-BROMOETHYL)-1,3-DIOXOLANE;3-BROMOPROPIONALDEHYDE ETHYLENE ACETAL
• CAS NO: 18742-02-4
• Molecular Formula: C₅H₉BrO₂
• Molecular Weight: 181.03
• EINECS: 242-551-1
• Product Categories: Acetals/Ketals/Ortho Esters;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Pyridines ,Heterocyclic Acids;Miscellaneous;Dioxanes & Dioxolanes;Dioxolanes
• Mol File: 18742-02-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 68-70 °C8 mm Hg(lit.)
• Flash Point: 149 °F
• Appearance: brownish-yellow/
• Density: 1.542 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.162mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: immiscible
• Sensitive: Light Sensitive
• BRN: 103516
• CAS DataBase Reference: 2-(2-Bromoethyl)-1,3-dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Bromoethyl)-1,3-dioxolane(18742-02-4)
• EPA Substance Registry System: 2-(2-Bromoethyl)-1,3-dioxolane(18742-02-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 2
• F: 8-9
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 18742-02-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to yellow or brown liquid

Uses

Different sources of media describe the Uses of 18742-02-4 differently. You can refer to the following data:
1. Alkylating agent for amines,1 dithianes,2 and carboximides,3 and via the Grignard reagent, aldehydes.4
2. 2-(2-Bromoethyl)-1,3-dioxolane is used as a pharmaceutical intermediate, dioxolanes, acetals, ketals, building blocks, chemical synthesis, organic building blocks and oxygen compounds. 1,1-(Ethylenedioxy)-3-bromopropane is used in the synthesis of EGFR inhibitors. Also used in the synthesis of orally active agents of cancer and cell proliferation with quinoline substructures. It is also used as flavouring agent.

General Description

Copper-catalyzed borylation of 2-(2-bromoethyl)-1,3-dioxolane with bis(pinacolato)diboron followed by treatment with potassium bifluoride affords the key organotrifluoroborate reagent.

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

• 168648-91-7 N-(2-[1,3]Dioxolan-2-yl-ethyl)-N-(3-methoxy-phenyl)-4-methyl-benzenesulfonamide 
• 182211-20-7 (2R,4R,5S)-2-(2'-bromoethyl)-N-ethoxycarbonyl-5-phenyl-4-methyl-1,3-oxazolidine 
• 182051-38-3 (2S,4S,5R)-2-(2'-bromoethyl)-N-ethoxycarbonyl-5-phenyl-4-methyl-1,3-oxazolidine 
• 179990-53-5 1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-3-[1,3]dioxolan-2-yl-propan-1-one 
• 188940-12-7 N-(2-[1,3]Dioxolan-2-yl-ethyl)-2-ethylsulfanylmethyl-N-methyl-benzamide 
• 202646-33-1 (3S,5S)-2-((E)-But-2-enyl)-5-(2-[1,3]dioxolan-2-yl-ethyl)-3-[1,3]dithian-2-yl-6-trimethylsilanyl-cyclohexanone 
• 904561-75-7 5-(2-[1,3]dioxolan-2-yl-ethylsulfanyl)-1-phenyl-1H-tetrazole 
• 251985-83-8 rac-4-([1,3]dioxolan-2-yl)-1,2-bis(4-methoxyphenyl)butan-1-one 
• 85391-14-6 3-(1,3-dioxolan-2-yl)propan-1-ol 
• 250695-50-2 (-)-menthyl-4-(1,3-dioxolane-2-yl)-2-hydroxy-2-methylbutanoate 
• 477959-75-4 1-[2-([1,3]dioxolan-2-yl)ethyl]-5-methylcyclohex-2-en-1-ol 
• 4360-60-5 2-phenethyl-[1,3]dioxolane 
• 600708-85-8 2-(2-hydroxyphenoxy)ethyl-1,3-dioxolane 
• 670247-25-3 3-[1,3]Dioxolan-2-yl-1-[2-((S)-2,2,2-trifluoro-1-methoxy-ethyl)-phenyl]-propan-1-ol 

Relevant articles and documents

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.

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

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.