4-Bromo-2-ethynyl-1-methoxybenzene

Base Information

• Chemical Name: 4-Bromo-2-ethynyl-1-methoxybenzene
• CAS No.: 1057669-94-9
• Molecular Formula: C9H7BrO
• Molecular Weight: 211.058
• DSSTox Substance ID: DTXSID40700693
• Wikidata: Q82632139
• Mol file: 1057669-94-9.mol

Synonyms:4-BROMO-2-ETHYNYL-1-METHOXYBENZENE;1057669-94-9;SCHEMBL14661858;DTXSID40700693;4-Bromo-2-ethynyl-1-methoxy-Benzene;AKOS016010851;A18055;EN300-1223570;A1-12688;F2147-2792

Chemical Property of 4-Bromo-2-ethynyl-1-methoxybenzene

Chemical Property:

• Boiling Point: 268.0±30.0 °C(Predicted)
• PSA: 9.23000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 2.43900
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 209.96803
• Heavy Atom Count: 11
• Complexity: 170

Purity/Quality:

98%min ^*data from raw suppliers

4-Bromo-2-ethynyl-1-methoxybenzene 95.00 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)Br)C#C

Technology Process of 4-Bromo-2-ethynyl-1-methoxybenzene

There total 4 articles about 4-Bromo-2-ethynyl-1-methoxybenzene 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: 95.0%

[(5-bromo-2-methoxyphenyl)ethynyl](trimethyl)silane (1421580-95-1) → 4-bromo-2-ethynyl-1-methoxybenzene (1057669-94-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/acs.joc.7b00538

Reference yield: 88.0%

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + 5-bromo-2-methoxybenzaldehyde (25016-01-7) → 4-bromo-2-ethynyl-1-methoxybenzene (1057669-94-9)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 20 ℃; for 6h;

DOI:10.1002/bkcs.11352

Reference yield:

4-bromo-2-iodo-anisole (98273-59-7) → 4-bromo-2-ethynyl-1-methoxybenzene (1057669-94-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; N-butylamine / diethyl ether / 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; N-butylamine; In tetrahydrofuran; diethyl ether; 1: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.joc.7b00538

upstream raw materials:

4-bromo-2-iodo-anisole

[(5-bromo-2-methoxyphenyl)ethynyl](trimethyl)silane

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

5-bromo-2-methoxybenzaldehyde

Refernces

• 1、 Chen, Chin-Chau,Wu, Man-Yun,Chen, Hsing-Yin,Wu, Ming-Jung. "Halogen-Mediated Cascade Cyclization Reaction of Aryldiynes to Indeno[1,2-c]chromene Derivatives". . p. 6071 - 6081. Retrieved 2017/06/23.