4-Acetoxy-3-bromoanisole

Base Information

• Chemical Name: 4-Acetoxy-3-bromoanisole
• CAS No.: 449727-85-9
• Molecular Formula: C9H9BrO3
• Molecular Weight: 245.073
• European Community (EC) Number: 610-219-9
• DSSTox Substance ID: DTXSID90461308
• Nikkaji Number: J1.749.635B
• Mol file: 449727-85-9.mol

Synonyms:4-ACETOXY-3-BROMOANISOLE;449727-85-9;(2-bromo-4-methoxyphenyl) acetate;SCHEMBL9280624;DTXSID90461308;FT-0713494

Chemical Property of 4-Acetoxy-3-bromoanisole

Chemical Property:

• Vapor Pressure: 0.00148mmHg at 25°C
• Boiling Point: 295.9oC at 760 mmHg
• Flash Point: 132.8oC
• PSA: 35.53000
• Density: 1.465g/cm3
• LogP: 2.38300
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 243.97351
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

98%Min ^*data from raw suppliers

4-ACETOXY-3-BROMOANISOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1=C(C=C(C=C1)OC)Br

Technology Process of 4-Acetoxy-3-bromoanisole

There total 2 articles about 4-Acetoxy-3-bromoanisole 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: 83.0%

Acetyl bromide (506-96-7) + 1-(benzyloxy)-2-bromo-4-methoxybenzene (151039-11-1) → acetic acid 2-bromo-4-methoxyphenyl ester (449727-85-9)

Guidance literature:

With lithium bromide; In dichloromethane; at 30 - 35 ℃; for 24h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo801659g

Reference yield:

4-methoxy-phenol (150-76-5) → acetic acid 2-bromo-4-methoxyphenyl ester (449727-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / tetrabutylammonium tribromide / methanol; CH₂Cl₂ / 20 °C

2: pyridine

With pyridine; tetra-N-butylammonium tribromide; In methanol; dichloromethane;

DOI:10.1016/j.tet.2004.07.041

Reference yield: 94.0%

acetic acid 2-bromo-4-methoxyphenyl ester (449727-85-9) + (R)-1-methoxy-4-((3-methylpent-4-ynyloxy)methyl)benzene (158817-25-5) → acetic acid 4-methoxy-2-[(R)-5-(4-methoxybenzyloxy)-3-methylpent-1-ynyl]phenyl ester (449727-86-0)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In acetonitrile; Heating;

DOI:10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8

upstream raw materials:

4-methoxy-phenol

Acetyl bromide

1-(benzyloxy)-2-bromo-4-methoxybenzene

Downstream raw materials:

acetic acid 4-methoxy-2-[(R)-5-(4-methoxybenzyloxy)-3-methylpent-1-ynyl]phenyl ester

acetic acid 2-[(R)-5-hydroxy-3-methylpent-1-ynyl]-4-methoxyphenyl ester

2-[(R)-3-(5-Methoxy-benzofuran-2-yl)-butyl]-cyclohexane-1,3-dione

2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran