3-Bromo-5-hydroxy-4-methoxybenzaldehyde

Base Information

• Chemical Name: 3-Bromo-5-hydroxy-4-methoxybenzaldehyde
• CAS No.: 23354-30-5
• Molecular Formula: C8H7BrO3
• Molecular Weight: 231.046
• Hs Code.: 2913000090
• ChEMBL ID: CHEMBL327667
• DSSTox Substance ID: DTXSID40513189
• Wikidata: Q82372853
• Mol file: 23354-30-5.mol

Synonyms:3-BROMO-5-HYDROXY-4-METHOXYBENZALDEHYDE;23354-30-5;CHEMBL327667;SCHEMBL2807788;DTXSID40513189;MB07646

Chemical Property of 3-Bromo-5-hydroxy-4-methoxybenzaldehyde

Chemical Property:

• PSA: 46.53000
• LogP: 1.97580
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 229.95786
• Heavy Atom Count: 12
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

3-BROMO-5-HYDROXY-4-METHOXYBENZALDEHYDE 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=C1Br)C=O)O

Technology Process of 3-Bromo-5-hydroxy-4-methoxybenzaldehyde

There total 10 articles about 3-Bromo-5-hydroxy-4-methoxybenzaldehyde 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: 94.0%

C8H7BF3O3(1-)*K(1+) → 3-bromo-4-methoxy-5-hydroxybenzaldehyde (23354-30-5)

Guidance literature:

With tetra-N-butylammonium tribromide; In tetrahydrofuran; water; at 20 ℃; for 0.666667h; chemoselective reaction;

DOI:10.1021/ol9027144

Reference yield: 92.0%

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) + methyl iodide (74-88-4) → 3-bromo-4-methoxy-5-hydroxybenzaldehyde (23354-30-5)

Guidance literature:

5-bromo-4-hydroxy-3-methoxybenzaldehyde; With pyridine; aluminum (III) chloride; In dichloromethane; Reflux;

With lithium carbonate; In dichloromethane; N,N-dimethyl-formamide; at 45 ℃; for 1h;

methyl iodide; In dichloromethane; N,N-dimethyl-formamide; at 45 ℃; for 5h;

DOI:10.1002/ejoc.201701243

Reference yield: 86.5%

vanillin (121-33-5,8014-42-4) → 3-bromo-4-methoxy-5-hydroxybenzaldehyde (23354-30-5)

Guidance literature:

With bromine; In methanol; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2010.12.063

upstream raw materials:

acetic acid 5-formyl-2-methoxy-3-nitrophenyl ester

diazomethane

3-bromo-4,5-dihydroxybenzaldehyde

methyl iodide

Downstream raw materials:

C₁₉H₁₇BrO₇S

5-bromoveratralaldehyde

C₂₅H₂₈O₃Si

C₃₉H₄₂ClNO₆Si

Refernces

• 1、 Khunnawutmanotham, Nisachon,Sahakitpichan, Poolsak,Chimnoi, Nitirat,Techasakul, Supanna. "Efficient One-Pot Synthesis of Tetrahydronaphtho[2,1-f]isoquinolines by Using Domino Pictet–Spengler/Friedel–Crafts-Type Reactions". . p. 6434 - 6440. Retrieved 2017/12/01.
• 2、 Sloman, David L.,Mitasev, Branko,Scully, Stephen S.,Beutler, John A.,Porco Jr., John A.. "Synthesis and biological evaluation of ABCD ring fragments of the kibdelones". supporting information; experimental part. p. 2511 - 2515. Retrieved 2011/05/04.