3,5-Difluoro-2,4-dihydroxybenzaldehyde

Base Information

• Chemical Name: 3,5-Difluoro-2,4-dihydroxybenzaldehyde
• CAS No.: 209541-27-5
• Molecular Formula: C₇H₄F₂O₃
• Molecular Weight: 174.104
• DSSTox Substance ID: DTXSID70596703
• Wikidata: Q82492025
• Mol file: 209541-27-5.mol

Synonyms:3,5-DIFLUORO-2,4-DIHYDROXYBENZALDEHYDE;209541-27-5;SCHEMBL8564158;DTXSID70596703;HOGLWUCRFJBQOZ-UHFFFAOYSA-N;MFCD24675922;AKOS024199525;AS-42283;DB-228459;CS-0435068

Chemical Property of 3,5-Difluoro-2,4-dihydroxybenzaldehyde

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 174.01285031
• Heavy Atom Count: 12
• Complexity: 176

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=C(C(=C1F)O)F)O)C=O

Technology Process of 3,5-Difluoro-2,4-dihydroxybenzaldehyde

There total 6 articles about 3,5-Difluoro-2,4-dihydroxybenzaldehyde 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: 60.0%

hexamethylenetetramine (100-97-0) + 2,4-difluorobenzene-1,3-diol (195136-71-1) → 3,5-Difluoro-2,4-dihydroxybenzaldehyde (209541-27-5)

Guidance literature:

With trifluoroacetic acid; Heating;

DOI:10.1016/S0960-894X(98)00578-2

Reference yield:

hexamethylenetetramine (100-97-0) + sulfuric acid (7664-93-9) + 2,4-difluorobenzene-1,3-diol (195136-71-1) → 3,5-Difluoro-2,4-dihydroxybenzaldehyde (209541-27-5)

Guidance literature:

In trifluoroacetic acid;

Reference yield:

1,3-difluoro-2,4-dimethoxy-5-nitrobenzene (195136-63-1) → 3,5-Difluoro-2,4-dihydroxybenzaldehyde (209541-27-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ammonium formate; palladium 10% on activated carbon / methanol / 0.5 h / 20 °C

2.1: hydrogenchloride; sodium nitrite / water / 0.67 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: boron tribromide / dichloromethane / 72 h / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / 0 °C / Inert atmosphere

4.2: 24 h / Inert atmosphere; Reflux

With hydrogenchloride; palladium 10% on activated carbon; ammonium formate; boron tribromide; trifluoroacetic acid; sodium nitrite; In methanol; dichloromethane; water;

DOI:10.1055/s-0035-1561603

upstream raw materials:

hexamethylenetetramine

2,4-difluorobenzene-1,3-diol

sulfuric acid

2,3,4,5-tetrafluoro-1-nitrobenzene

Downstream raw materials:

6,8-difluoro-7-hydroxycoumarin-3-carboxylic acid

Refernces

• 1、 Kerkovius, Jeff K.,Menard, Frederic. "A Practical Synthesis of 6,8-Difluoro-7-hydroxycoumarin Derivatives for Fluorescence Applications". . p. 1622 - 1629. Retrieved 2016/05/24.