2-(2-Bromoethyl)-1,3-dioxolane

Base Information

• Chemical Name: 2-(2-Bromoethyl)-1,3-dioxolane
• CAS No.: 18742-02-4
• Molecular Formula: C5H9BrO2
• Molecular Weight: 181.029
• Hs Code.: 29329990
• European Community (EC) Number: 242-551-1
• UNII: 4SY9FQ278P
• DSSTox Substance ID: DTXSID40172058
• Nikkaji Number: J208.097D
• Wikidata: Q72455449
• Mol file: 18742-02-4.mol

Synonyms:2-(2-Bromoethyl)-1,3-dioxolane;18742-02-4;3-Bromopropionaldehyde ethylene acetal;1,3-Dioxolane, 2-(2-bromoethyl)-;1,1-(Ethylenedioxy)-3-bromopropane;4SY9FQ278P;2-(2-Bromoethyl)-1,3-dioxolane, Tech grade;EINECS 242-551-1;EC 242-551-1;2-[2-Bromoethyl]-1,3-dioxolane;MFCD00003216;bromoethyl-1,3-dioxolane;UNII-4SY9FQ278P;2-(2-bromoethyl)-dioxolane;SCHEMBL45855;2-(bromoethyl)-1,3-dioxolane;2(2-bromoethyl)-1,3-dioxolane;DTXSID40172058;2-(2-bromoethyl)-1,3-dioxolan;2-(2-bromoethyl) 1,3-dioxolane;2-(2-bromoethyl)-[1,3]dioxolane;2-(2-bromoethyl)-1, 3-dioxolane;2-(2-bromo-ethyl)-[1,3]dioxolane;AKOS009159413;3-BROMOPROPANAL ETHYLENE ACETAL;CS-W019935;1,3-DIOXOLAN-2-YLETHYL BROMIDE;2-[1,3]-dioxolan-2-yl-1-bromoethane;AS-18184;2-(2-Bromoethyl)-1,3-dioxolane, 96%;3,3-(ETHYLENEDIOXY)PROPYL BROMIDE;1-BROMO-3,3-(ETHYLENEDIOXY)PROPANE;AM20090095;B1132;FT-0608434;FT-0608435;EN300-42499;N-(3-chloropropyl)-N-cyclohexylcyclohexanamine;.BETA.-BROMOPROPIONALDEHYDE ETHYLENE ACETAL;A813149;W-107771;F2190-0182;2-(2-Bromoethyl)-1,3-dioxolane, purum, >=97.0% (GC), brownish-yellow

Chemical Property of 2-(2-Bromoethyl)-1,3-dioxolane

Chemical Property:

• Appearance/Colour: Clear colorless to yellow or brown liquid
• Vapor Pressure: 0.162mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Boiling Point: 200.9 °C at 760 mmHg
• Flash Point: 85 °C
• PSA: 18.46000
• Density: 1.489 g/cm³
• LogP: 1.14430
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Water Solubility.: immiscible
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 179.97859
• Heavy Atom Count: 8
• Complexity: 61.4

Purity/Quality:

99% ^*data from raw suppliers

1,1-(Ethylenedioxy)-3-bromopropane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1COC(O1)CCBr
• Uses: Alkylating agent for amines,1 dithianes,2 and carboximides,3 and via the Grignard reagent, aldehydes.4 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.

Technology Process of 2-(2-Bromoethyl)-1,3-dioxolane

There total 5 articles about 2-(2-Bromoethyl)-1,3-dioxolane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

ethylene glycol (107-21-1) + acrolein (107-02-8,25068-14-8) → 2-bromo-2-(2-ethyl)dioxolane (18742-02-4)

Guidance literature:

With hydrogen bromide; In 1,4-dioxane; at 5 - 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2017.02.020

Reference yield: 55.0%

2-vinyl-1,3-dioxolane (3984-22-3) → 2-bromo-2-(2-ethyl)dioxolane (18742-02-4)

Guidance literature:

With chloro-trimethyl-silane; sodium bromide; at 22 ℃; for 1.5h;

Reference yield:

3-bromopropanal (65032-54-4) + ethylene glycol (107-21-1) → 2-bromo-2-(2-ethyl)dioxolane (18742-02-4)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 20h; Reflux;

DOI:10.1016/j.bmcl.2021.127975

upstream raw materials:

2-vinyl-1,3-dioxolane

ethylene glycol

acrolein

3-bromopropanal

Downstream raw materials:

(-)-menthyl-4-(1,3-dioxolane-2-yl)-2-hydroxy-2-methylbutanoate

2-(3,4-dimethoxy-phenyl)-4-[1,3]dioxolan-2-yl-butyronitrile

2-phenethyl-[1,3]dioxolane

1-Benzyl-3-(2-[1,3]dioxolan-2-yl-ethyl)-5-methyl-1H-pyrimidine-2,4-dione

Refernces

Asymmetricsynthesis. XXXII. Formalsynthesisof (-) - Perhydrohistrionicotoxin

10.1016/S0040-4039(00)74361-9

The study details the enantioselective synthesis of (-)-depentylperhydrohistrionicotoxin 2 from the chiral synthon (-)-3. The key steps involve the formation of a spiro skeleton through an aldol cyclization of a methyl ketone and an aldehyde function. The synthesis strategy includes the condensation of (-)-3 with 2-(2-bromoethyl)-1,3-dioxolane to form 4, which upon treatment with MeLi yields imine 5. The tricyclic ketal 6 is isolated instead of the expected ketone, and its ether system is reduced with LAH/AlCl3 to form an epimeric mixture of alcohols 7. Further steps include hydrogenation, protection with benzyl bromide, Swem oxidation to ketone 9, and a series of transformations involving 1,4-reduction, butyl chain addition, dehydration, and hydroboration-oxidation to finally yield (-)-depentylperhydrohistrionicotoxin 2. The study highlights the challenges and innovative solutions in synthesizing complex natural products with high stereochemical control.

The Cinchona alkaloids: A silicon-directed synthesis of some advanced intermediates

10.1021/jo00015a036

The research focuses on the synthesis of advanced intermediates of Cinchona alkaloids using silicon-directed reactions. The purpose of the study is to develop a more efficient and scalable synthetic route for these alkaloids, which are historically significant therapeutic agents, particularly quinine and quinidine. The key chemicals used in the research include benzylamine, 2-(2-bromoethyl)-1,3-dioxolane, 3-(trimethylsilyl)-2(E)-propenoyl chloride, 1-(triphenylphosphoranylidene)-2-propanone, and various other reagents such as lithium aluminum hydride, sodium borohydride, and ceric ammonium nitrate (CAN). The study concludes that a silicon-directed Baeyer-Villager oxidation is an effective method to achieve the desired transformation, yielding N-benzylmeroquinene aldehyde in good yield. The researchers also successfully synthesized alcohols 23a,b and acetates 24a,b, which are advanced intermediates for the Cinchona alkaloids. The research demonstrates the utility of silicon-directed reactions in the synthesis of complex natural products, providing a potentially more accessible route for the production of these valuable compounds.

Second-generation process research towards eletriptan: A fischer indole approach

10.1021/op100251q

The study presents the development of a second-generation synthetic process for eletriptan, a drug used to treat migraines, employing a Fischer indole cyclization approach. The new process aims to overcome the limitations of the existing manufacturing route, which includes the use of expensive and harmful starting materials, and generates significant waste. The research details the synthesis of key intermediates, such as aldehyde 8 and hydrazine 10, and explores various methods to improve yield and scalability. The study also discusses the successful application of the Fischer indole reaction to synthesize eletriptan and the optimization of the process using L-ascorbic acid for the reduction of diazonium salts to aryl hydrazines, resulting in a more cost-effective, efficient, and environmentally friendly synthesis route. The final objective was achieved by synthesizing the single enantiomer of eletriptan (R)-7 through classical resolution techniques, offering a potentially more sustainable and scalable method for its production.