1-(5-Chloro-2-hydroxyphenyl)-1,3-butanedione

Base Information

• Chemical Name: 1-(5-Chloro-2-hydroxyphenyl)-1,3-butanedione
• CAS No.: 240424-48-0
• Molecular Formula: C₁₁H₁₂BrClO₄
• Molecular Weight: 323.571
• European Community (EC) Number: 636-635-0
• DSSTox Substance ID: DTXSID20404460
• Nikkaji Number: J1.114.901D
• Wikidata: Q82208670
• Mol file: 240424-48-0.mol

Synonyms:1-(5-Chloro-2-hydroxyphenyl)-1,3-butanedione;65897-66-7;1-(5-chloro-2-hydroxyphenyl)butane-1,3-dione;starbld0013533;SCHEMBL14706719;DTXSID20404460;AKOS015913474;1-(5-Chloro-2-hydroxyphenyl)1,3-butaned;240424-48-0

Chemical Property of 1-(5-Chloro-2-hydroxyphenyl)-1,3-butanedione

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 212.0240218
• Heavy Atom Count: 14
• Complexity: 240

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)CC(=O)C1=C(C=CC(=C1)Cl)O

Technology Process of 1-(5-Chloro-2-hydroxyphenyl)-1,3-butanedione

There total 1 articles about 1-(5-Chloro-2-hydroxyphenyl)-1,3-butanedione 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: 92.0%

2-Methoxyethoxymethyl chloride (3970-21-6) + 3-bromo-5-chlorosalicylaldehyde (19652-32-5) → 3-bromo-5-chloro-2-[(2-methoxyethoxy)methoxy]benzaldehyde (240424-48-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 25 ℃; for 3.83333h; Sealed tube; Inert atmosphere; Large scale;

DOI:10.1021/op034094j

Reference yield: 65.0%

3-bromo-5-chloro-2-[(2-methoxyethoxy)methoxy]benzaldehyde (240424-48-0) + dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) → 1-bromo-5-chloro-3-ethynyl-2-(2-methoxyethoxymethoxy)benzene

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2015.09.042

Reference yield:

3-bromo-5-chloro-2-[(2-methoxyethoxy)methoxy]benzaldehyde (240424-48-0) → 1,1-dimethylethyl (S)-3-bromo-5-chloro-2-[(2-methoxyethoxy)methoxy]-β-[[(1S)-2-hydroxy-1-phenylethyl]amino]benzenepropanoate (240424-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: MgSO₄ / toluene / 2 h / 22 °C

2.1: Zn metal / tetrahydrofuran / 1 h / 50 °C

2.2: 1-methyl-pyrrolidin-2-one; tetrahydrofuran / 3 h / -8 °C

With magnesium sulfate; zinc; In tetrahydrofuran; toluene; 2.2: Reformatsky coupling;

DOI:10.1021/jo050177h

upstream raw materials:

2-Methoxyethoxymethyl chloride

3-bromo-5-chlorosalicylaldehyde

Downstream raw materials:

1,1-dimethylethyl (S)-3-bromo-5-chloro-2-[(2-methoxyethoxy)methoxy]-β-[[(1S)-2-hydroxy-1-phenylethyl]amino]benzenepropanoate