Triacetylphloroglucinol
Basic information
- CAS
2161-87-7- Standard SMILES
CC(=O)c1c(O)c(C(C)=O)c(O)c(C(C)=O)c1O- InChIKey
YOQHLDOEJYEQRA-UHFFFAOYSA-N- Molecular formula
- C12H12O6
- Average molar mass
- 252.22 g/mol
- Monoisotopic mass
- 252.0633881
Overview
Triacetylphloroglucinol is an aromatic ketone.
Names & identifiers
- Preferred name
- Triacetylphloroglucinol
- IUPAC
- 1-(3,5-diacetyl-2,4,6-trihydroxyphenyl)ethanone
- English name
- 2,4,6-Triacetylphloroglucinol
- Molecular formula
- C12H12O6
- Molecular weight
- 252.22
Names & synonyms
triacetylphloroglucinol2161-87-72,4,6-Triacetylphloroglucinol1-(3,5-diacetyl-2,4,6-trihydroxyphenyl)ethanone1,1',1''-(2,4,6-Trihydroxybenzene-1,3,5-triyl)triethanoneMFCD057388991,1',1''-(2,4,6-trihydroxybenzene-1,3,5-triyl)tris(ethan-1-one)Phloroglucinol 2,4,6-TriacetatePhloroglucinol Triacetyl1,3,5-Triacetyl-2,4,6-trihydroxybenzene1-(3,5-diacetyl-2,4,6-trihydroxyphenyl)ethan-1-oneSCHEMBL6023652
Show more names
Penicillamine Impurity 19Ethanone, 1,1',1''-(2,4,6-trihydroxy-1,3,5-benzenetriyl)tris-
DTXSID20356490CHEBI:201659Ethanone,1,1',1''-(2,4,6-trihydroxy-1,3,5-benzenetriyl)tris-STL185496AKOS025264475SY4872402,4,6-triacetyl-1,3,5-trihydroxybenzeneDB-260341
Database identifiers
- CAS
2161-87-7- PubChem CID
- 824901
- DTXSID
DTXSID20356490- ChEBI
CHEBI:201659- Nikkaji
- J2.081.146C
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 302
Physicochemical properties
- Melting point
- 145 · 145-147°C
- Boiling point
- 501.4 · 501.4±50.0 °C(Predicted)
- Density
- 1.406 · 1.406±0.06 g/cm3(Predicted)
- storage temp.
- Amber Vial, Refrigerator
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 7.69 · 7.69±0.33(Predicted)
- color
- Off-White to Beige
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P362+P364-P332+P313-P337+P313-P403+P233-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P362+P364-P332+P313-P337+P313-P403+P233-P405-P501
Chemistry & industry
Applications
DescriptionTriacetylphloroglucinol 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.
UsesTriacetylphloroglucinol (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.
Uses2,4,6-Triacetylphloroglucinol (cas# 2161-87-7) is a compound useful in organic synthesis.
Preparation methods
PreparationObtained by Friedel–Crafts acylation of phloroglucinol, with acetic anhydride in the presence of boron trifluoride in acetic acid at r.t. (60%) ; with acetyl chloride in the presence of aluminium chloride in ethyl ether at r.t. for 6 days (17%); with acetyl chloride and acetic acid in the presence of ferric chloride in ethyl acetate.
Upstream & downstream products
Downstream products
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Compound notes
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