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:

1-<2-(1,3-dioxolan-2-yl)ethyl>-2,5-cyclohexadiene-1-carboxylic acid

1-Chloro-2-(4-chloro-phenyl)-4-[1,3]dioxolan-2-yl-butan-2-ol

N-{6-[(2-[1,3]Dioxolan-2-yl-ethyl)-(toluene-4-sulfonyl)-amino]-acridin-3-yl}-acetamide

ethyl 4-(1,3-dioxolan-2-yl)-2-(4-methoxymethoxyphenyl)butyrate

Refernces

• 1、 Nishio, Yuya,Mifune, Ryota,Sato, Taisuke,Ishikawa, Shin-ich,Matsubara, Hiroshi. "Preparation and properties of a novel solution of hydrogen bromide (HBr) in 1,4-dioxane: An alternative reagent to HBr gas without protic solvents". . p. 1190 - 1193. Retrieved 2017/03/02.
• 2、 Cordova, Armando,Lin, Shuangzheng,Tseggai, Abrehet. "Concise catalytic asymmetric total synthesis of biologically active tropane alkaloids". supporting information; experimental part. p. 1363 - 1372. Retrieved 2012/06/18.