Triacetylphloroglucinol

Base Information

• Chemical Name: Triacetylphloroglucinol
• CAS No.: 2161-87-7
• Molecular Formula: C12H12 O6
• Molecular Weight: 252.224
• Hs Code.: 2914501900
• DSSTox Substance ID: DTXSID20356490
• Wikidata: Q82135839
• Mol file: 2161-87-7.mol

Synonyms:triacetylphloroglucinol;2161-87-7;2,4,6-Triacetylphloroglucinol;1-(3,5-diacetyl-2,4,6-trihydroxyphenyl)ethanone;SCHEMBL6023652;DTXSID20356490;STL185496;AKOS025264475;FT-0675383;AD-341/40841630;J-014185;1-(3,5-diacetyl-2,4,6-trihydroxyphenyl)ethan-1-one;1,1',1''-(2,4,6-Trihydroxybenzene-1,3,5-triyl)triethanone

Chemical Property of Triacetylphloroglucinol

Chemical Property:

• Melting Point: 145-147°C
• Boiling Point: 501.4±50.0 °C(Predicted)
• PKA: 7.69±0.33(Predicted)
• Flash Point: 271.2oC
• PSA: 111.90000
• Density: 1.406±0.06 g/cm3(Predicted)
• LogP: 1.41120
• Storage Temp.: Amber Vial, Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 252.06338810
• Heavy Atom Count: 18
• Complexity: 302

Purity/Quality:

95% ^*data from raw suppliers

2,4,6-Triacetylphloroglucinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C(=C(C(=C1O)C(=O)C)O)C(=O)C)O
• Description: Triacetylphloroglucinol is a C3-symmetric tritopic bridging ligand. It has been used in the synthesis of various compounds, including trinuclear vanadium Schiff base complexes, copper complexes, and anthelmintics.
• Uses: Triacetylphloroglucinol (TAPG) is the most hydrophobic of a small molecular weight phenolic metabolite belonging to the phloroglucinol (1,3,5 trihydroxybenzene) family, produced by bacteria including Pseudomonas strains. TAPG exhibits a broad range of biological activities, albeit with mostly low potency. In the search for novel actives, TAPG and related metabolites are important for dereplication to eliminate leads due to high amounts of weakly potent actives. Although weakly active, this family appears to be important in the biocontrol of plant diseases by some Pseudomonas strains. 2,4,6-Triacetylphloroglucinol (cas# 2161-87-7) is a compound useful in organic synthesis.

Technology Process of Triacetylphloroglucinol

There total 15 articles about Triacetylphloroglucinol 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: 91.0%

1,3,5-Trihydroxybenzene dihydrate (6099-90-7) + acetyl chloride (75-36-5) → 1,3,5-triacetyl-2,4,6-trihydroxybenzene (2161-87-7)

Guidance literature:

With aluminum (III) chloride; for 1h; Reagent/catalyst; Time; Reflux;

DOI:10.1016/j.molstruc.2014.10.059

Reference yield: 83.0%

3,5-dihydroxyphenol (108-73-6) + acetic anhydride (108-24-7) + acetic acid (64-19-7,77671-22-8) → 1,3,5-triacetyl-2,4,6-trihydroxybenzene (2161-87-7)

Guidance literature:

With methanesulfonic acid; at 80 ℃; for 12h;

DOI:10.1016/j.bioorg.2018.12.035

Reference yield: 68.0%

1,3,5-triacetoxybenzene (2999-40-8) → 1,3,5-triacetyl-2,4,6-trihydroxybenzene (2161-87-7)

Guidance literature:

With N,N-dimethyl-formamide; zinc; at 87 ℃; for 23h; microwave irradiation;

DOI:10.1055/s-2004-829152

upstream raw materials:

methyl magnesium iodide

diethyl ether

carbon suboxide

1,3,5-triacetoxybenzene

Downstream raw materials:

2,4-diacetylphloroglucinol

2,4,6-trihydroxyacetophenone

2,4,6-tribromophloroglucinol

2,4,6-Triethyl-1,3,5-benzoltriol