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T89702

Sigma-Aldrich

Tropolone

98%

Synonym(s):

2-Hydroxy-2,4,6-cycloheptatrien-1-one

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About This Item

Empirical Formula (Hill Notation):
C7H6O2
CAS Number:
533-75-5
Molecular Weight:
122.12
Beilstein:
1904978
EC Number:
208-577-2
MDL number:
MFCD00004158
UNSPSC Code:
12352100
PubChem Substance ID:
24900578
NACRES:
NA.22

Quality Level

300

Assay

98%

bp

80-84 °C/0.1 mmHg (lit.)

mp

50-52 °C (lit.)

storage temp.

2-8°C

SMILES string

OC1=CC=CC=CC1=O

InChI

1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)

InChI key

MDYOLVRUBBJPFM-UHFFFAOYSA-N

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Application

Tropolone is a sensitive reagent for reducing sugars. It is also an organic chelator that can form complexes with trivalent lathanide ions (Eu3+, Gd3+, and Tb3+).
It can also be used as:
  • A precursor to synthesize azulene derivatives such as methyl 2-methylazulene-1-carboxylate.
  • A reagent to prepare fused heterocycles and complexes of Ga(III) and In(III).

Signal Word

Danger

Hazard Statements

H314,H317,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

233.6 °F - closed cup

Flash Point(C)

112 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Spectroscopy and non-radiative processes in Gd3+, Eu3+ and Tb3+ tropolonates.
Santos BS, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 54(13), 2237-2245 (1998)
Trends Heterocycl. Chem., 1, 137-137 (1990)
Structural characterization of two lipophilic tris(tropolonato) gallium(III) and indium(III) complexes of radiopharmaceutical interest
F.Nepveu and F.JasanadaL.Walz
Inorgorganica Chimica Acta, 211, 141-141 (1993)
Jinbing Liu et al.
European journal of medicinal chemistry, 44(4), 1773-1778 (2008-06-06)
A series of alkylidenethiosemicarbazide compounds were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that most of the synthesized compounds exhibited significant inhibitory activities. Especially, compound 1f was found to be
Jessica L Fullagar et al.
Chemical communications (Cambridge, England), 49(31), 3197-3199 (2013-03-14)
Tropolone emerged from the screening of a chelator fragment library (CFL) as an inhibitor of the Zn(2+)-dependent virulence factor, Pseudomonas aeruginosa elastase (LasB). Based on this initial hit, a series of substituted tropolone-based LasB inhibitors was prepared, and a compound
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