Description

Tropolone (CAS 533-75-5) is a versatile organic compound with the molecular formula C₇H₆O₂ and IUPAC name 2-hydroxycyclohepta-2,4,6-trien-1-one. This pale yellow crystalline solid exhibits unique chelating properties due to its seven-membered aromatic ring structure with a hydroxyl and ketone functional group. Tropolone is widely recognized for its role as a ligand in coordination chemistry, forming stable complexes with various metal ions. With a melting point of 50-52°C and boiling point of 140°C at 20 mmHg, it demonstrates good solubility in organic solvents like ethanol and ether while being sparingly soluble in water. Researchers value tropolone for its antimicrobial, antifungal, and anti-inflammatory properties, making it valuable in pharmaceutical and biochemical studies. The compound is supplied with ≥98% purity (GC) and is packaged under inert gas to ensure stability.

Properties

• CAS Number: 533-75-5
• Complexity: 209
• IUPAC Name: 2-hydroxycyclohepta-2,4,6-trien-1-one
• InChI: InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
• InChI Key: MDYOLVRUBBJPFM-UHFFFAOYSA-N
• Exact Mass: 122.036779430
• Molecular Formula: C7H6O2
• Molecular Weight: 122.12
• SMILES: C1=CC=C(C(=O)C=C1)O
• Topological: 37.3
• Monoisotopic Mass: 122.036779430
• Physical Description: Colorless solid; Light yellow to cream hygroscopic solid;
• Vapor Pressure: 0.000679 [mmHg]
• Synonyms: Tropolone, 2-Hydroxycyclohepta-2,4,6-trienone, Purpurocatechol, 2-Hydroxytropone, 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-, Tropomyosins, CCRIS 6609, EINECS 208-577-2, NSC 89303, BRN 1904978, 7L6DL16P1T, 2-Hydroxy-2,4,6-cycloheptatriene-1-one, DTXSID8049416, CHEBI:79966, TROPOLONE [MI], .ALPHA.-TROPOLONE, NSC-89303, TROPOLONE [WHO-DD], DTXCID7029376, 4-08-00-00159 (Beilstein Handbook Reference), 2Hydroxytropone, ALPHA-TROPOLONE, TROPOLONE [INCI], 2Hydroxy2,4,6cycloheptatrienone, 2Hydroxycyclohepta2,4,6trienone, 2Hydroxy2,4,6cycloheptatrien1one, 2,4,6Cycloheptatrien1one, 2hydroxy, mdyolvrubbjpfm-uhfffaoysa-n, 533-75-5, 2-hydroxycyclohepta-2,4,6-trien-1-one, 2-Hydroxy-2,4,6-cycloheptatrien-1-one, 2-Hydroxy-2,4,6-cycloheptatrienone, MFCD00004158, NSC89303, CHEMBL121188, UNII-7L6DL16P1T, 0TR, Tropolone, 98%, NCIMech_000829, SCHEMBL42739, SCHEMBL5481260, HY-N7135, Tox21_202924, AC1614, BDBM50236983, CCG-35867, s5688, 2-Hydroxy-cyclohepta-2,4,6-trienone, AKOS015900394, Tropolone, purum, >=98.0% (GC), CS-W013560, 2,6-Cycloheptatrien-1-one, 2-hydroxy-, NCGC00260470-01, AC-25757, AS-14018, CAS-533-75-5, NCI60_041986, SY009930, 2-hydroxy-2,4,6-cycloheptatrien -1-one, 1,4,6-Cycloheptatrien-1-one, 2-hydroxy-, DB-052324, NS00032738, ST50998276, T0606, EN300-124250, Q19952843, F0001-1377, InChI=1/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9

Application

Tropolone serves as a key intermediate in organic synthesis and metal chelation studies. It demonstrates significant biological activity as an inhibitor of metalloenzymes, particularly in research on antibacterial and antifungal agents. The compound’s ability to form stable complexes with transition metals makes it valuable in catalytic systems and materials science applications.

Safety and Hazards

GHS Hazard Statements

• H314 (85%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H317 (85%): May cause an allergic skin reaction [Warning Sensitization, Skin]
• H318 (85%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H400 (85%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
• H410 (85%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P260, P261, P264, P264+P265, P272, P273, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P333+P317, P362+P364, P363, P391, P405, and P501

Hazard Classes and Categories

• Skin Corr. 1B (85%)
• Skin Sens. 1B (85%)
• Eye Dam. 1 (85%)
• Aquatic Acute 1 (85%)
• Aquatic Chronic 1 (85%)

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