2-Bromo-1,1-diethoxyethene

Base Information

• Chemical Name: 2-Bromo-1,1-diethoxyethene
• CAS No.: 42520-11-6
• Molecular Formula: C6H11BrO2
• Molecular Weight: 195.056
• DSSTox Substance ID: DTXSID20446042
• Nikkaji Number: J331.876A
• Mol file: 42520-11-6.mol

Synonyms:2-bromo-1,1-diethoxyethene;42520-11-6;Ethene, 2-bromo-1,1-diethoxy-;DTXSID20446042;YLLVBVCUIFAFMS-UHFFFAOYSA-N;AKOS037503769

Chemical Property of 2-Bromo-1,1-diethoxyethene

Chemical Property:

• PSA: 18.46000
• LogP: 2.25320
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 193.99424
• Heavy Atom Count: 9
• Complexity: 83.1

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=CBr)OCC

Technology Process of 2-Bromo-1,1-diethoxyethene

There total 6 articles about 2-Bromo-1,1-diethoxyethene 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: 51.0%

1,1-dibromo-2,2-diethoxy-ethane (761-17-1) → 1,1-diethoxy-2-bromo-ethene (42520-11-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere; Cooling with ice;

DOI:10.1002/anie.201811717

Reference yield:

diethyl acetal (105-57-7,30846-29-8) → 1,1-diethoxy-2-bromo-ethene (42520-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 10 - 15 °C / Bromieren

2: potassium ethylate

With pyridine; potassium ethoxide;

Reference yield:

Bromoacetaldehyde diethyl acetal (2032-35-1) → 1,1-diethoxy-2-bromo-ethene (42520-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / diethyl ether / 20 h / 20 °C / Inert atmosphere; Cooling with ice

2: potassium tert-butylate / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Cooling with ice

With potassium tert-butylate; bromine; In tetrahydrofuran; diethyl ether;

DOI:10.1002/anie.201811717

upstream raw materials:

1,1-dibromo-2,2-diethoxy-ethane

potassium ethoxide

potassium tert-butylate

diethyl acetal

Downstream raw materials:

ethyl dibromoacetate

ethyl 3,3-bis(4'-methoxyphenyl)prop-2-enoate

ethoxytriethylsilane

(triethylsilyl)ethoxyacetylene

Refernces

• 1、 Walker, James R.,Merit, Jeffrey E.,Thomas-Tran, Rhiannon,Tang, Doris T. Y.,Du Bois. "Divergent Synthesis of Natural Derivatives of (+)-Saxitoxin Including 11-Saxitoxinethanoic Acid". . p. 1689 - 1693. Retrieved 2019.