cis-1-Bromo-2-ethoxyethylene

Base Information

• Chemical Name: cis-1-Bromo-2-ethoxyethylene
• CAS No.: 23521-49-5
• Molecular Formula: C4H7BrO
• Molecular Weight: 151.003
• Hs Code.: 29091990
• European Community (EC) Number: 245-712-4
• NSC Number: 617631
• DSSTox Substance ID: DTXSID601310860
• Nikkaji Number: J228.987C
• Mol file: 23521-49-5.mol

Synonyms:cis-1-Bromo-2-ethoxyethylene;23521-49-5;(Z)-1-bromo-2-ethoxyethene;Z-1-Bromo-2-ethoxyethene;cis-2-Bromovinyl ethyl ether;(Z)-1-Bromo-2-ethoxy-ethylene;EINECS 245-712-4;MFCD00042604;1-Bromo-2-ethoxyethyl-(Z)-ene;NSC617631;cis-2-Ethoxyvinyl bromide;(Z)-2-ethoxy-1-bromoethene;SCHEMBL376777;(1Z)-1-Bromo-2-ethoxyethene;BCFCTTHZFYZOHT-ARJAWSKDSA-N;DTXSID601310860;YAA52149;BBL103843;STL557653;AKOS015843285;GS-4543;NSC-617631;AM806384;J-015140;J-525168;cis-1-Bromo-2-ethoxyethylene, technical, ~85% (GC);Ethyl (2R,3S)-2-tert-butyloxycarbonylamino-3-phenyl-3-hydroxypropanoate

Chemical Property of cis-1-Bromo-2-ethoxyethylene

Chemical Property:

• Appearance/Colour: clear light yellow liquid
• Vapor Pressure: 13.1mmHg at 25°C
• Refractive Index: n20/D 1.474
• Boiling Point: 128.3 °C at 760 mmHg
• Flash Point: 47.8 °C
• PSA: 9.23000
• Density: 1.42 g/mL at 20 °C(lit.)
• LogP: 1.88900
• Storage Temp.: −20°C
• Solubility.: Chloroform, Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 149.96803
• Heavy Atom Count: 6
• Complexity: 42.8

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cis-1-Bromo-2-ethoxyethylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,H226
• Statements: 10
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC=CBr
• Isomeric SMILES: CCO/C=C\Br

Technology Process of cis-1-Bromo-2-ethoxyethylene

There total 8 articles about cis-1-Bromo-2-ethoxyethylene 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: 81.0%

ethyl vinyl ether (109-92-2,25104-37-4) → (Z)-1-bromo-2-ethoxyethene (23521-49-5)

Guidance literature:

ethyl vinyl ether; With bromine; Inert atmosphere; Schlenk technique;

With triethylamine; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.201403603

Reference yield:

1,2-dibromoethyl ethyl ether (2983-26-8) → ethyl bromide (74-96-4) + ethanol (64-17-5) + (Z)-1-bromo-2-ethoxyethene (23521-49-5) + (E)-1-bromo-2-ethoxyethene (16339-88-1) + Bromoacetaldehyde diethyl acetal (2032-35-1) + 1-ethoxyacetylene (927-80-0)

Guidance literature:

With N,N-diethylaniline; at 98 ℃; for 2.5h; Product distribution; other bases, var. conditions;

DOI:10.1021/jo00369a004

Reference yield:

1,2-dibromoethyl ethyl ether (2983-26-8) → (Z)-1-bromo-2-ethoxyethene (23521-49-5) + (E)-1-bromo-2-ethoxyethene (16339-88-1)

Guidance literature:

With N,N-diethylaniline;

DOI:10.1002/pol.1955.120168240

upstream raw materials:

1,2-dibromoethyl ethyl ether

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

ethyl vinyl ether

2-ethoxy-1,1-dibromo-ethene

Downstream raw materials:

1-ethoxyacetylene

(5S,6R)-5-acetyl-6-(2-ethoxyethenyl)-5-methylcyclohexa-1,3-diene-1-carboxaldehyde

(5R,6S)-5-acetyl-6-(2-ethoxyethenyl)-5-methylcyclohexa-1,3-diene-1-carboxaldehyde

N-(2-(2-bromo-1-ethoxyethoxy)phenyl)formamide

Refernces

• 1、 Henry, Cyril,Bolien, David,Ibanescu, Bogdan,Bloodworth, Sally,Harrowven, David C.,Zhang, Xunli,Craven, Andy,Sneddon, Helen F.,Whitby, Richard J.. "Generation and trapping of ketenes in flow". . p. 1491 - 1499. Retrieved 2015/03/04.
• 2、 Pericas, Miquel A.,Serratosa, Felix,Valenti, Eduard. "AN EFFICIENT SYNTHESIS OF tert-ALKOXYETHYNES". . p. 2311 - 2316. Retrieved 2007/10/02.