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T89702

Sigma-Aldrich

Tropolone

98%

Synonym(s):

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

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1 G
434,00 kr.
5 G
1.660,00 kr.
25 G
7.820,00 kr.

434,00 kr.

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1 G
434,00 kr.
5 G
1.660,00 kr.
25 G
7.820,00 kr.

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
Assay:
98%

434,00 kr.

Please contact Customer Service for Availability
Request a Bulk Order

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+).[1]
It can also be used as:
  • A precursor to synthesize azulene derivatives such as methyl 2-methylazulene-1-carboxylate.[2]
  • A reagent to prepare fused heterocycles[3] and complexes of Ga(III) and In(III).[4]

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR2835
SHBS0169
SHBR6029
SHBR7696
SHBR9806

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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)
Jack Davison et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(20), 7642-7647 (2012-04-18)
A gene cluster encoding the biosynthesis of the fungal tropolone stipitatic acid was discovered in Talaromyces stipitatus (Penicillium stipitatum) and investigated by targeted gene knockout. A minimum of three genes are required to form the tropolone nucleus: tropA encodes a
Tomasz Borowski et al.
Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 17(6), 881-890 (2012-05-25)
6-Hydroxymethyl-6-methylcyclohexa-2,4-dienone is a mechanistic probe which when incubated with an extradiol dioxygenase yields a 2-tropolone product. This observation was originally interpreted as evidence supporting a direct heterolytic 1,2-alkenyl migration mechanism for a ring expansion reaction catalyzed by this class of
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