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252832

Sigma-Aldrich

Tropone

97%

Synonym(s):

2,4,6-Cycloheptatrien-1-one

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About This Item

Empirical Formula (Hill Notation):
C7H6O
CAS Number:
539-80-0
Molecular Weight:
106.12
Beilstein:
1902335
EC Number:
208-725-6
MDL number:
MFCD00014331
UNSPSC Code:
12352100
PubChem Substance ID:
24855242
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.615 (lit.)

bp

113 °C/15 mmHg (lit.)

density

1.094 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

O=C1C=CC=CC=C1

InChI

1S/C7H6O/c8-7-5-3-1-2-4-6-7/h1-6H

InChI key

QVWDCTQRORVHHT-UHFFFAOYSA-N

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General description

Metal-catalyzed [6+3] cycloaddition of tropone with azomethine ylides has been reported.

Application

Tropone has been used in synthesis of:
  • bicyclic δ-lactones via heterocyclic carbine-catalyzed [8+3] annulation pathway
  • 6,7-benzobicyclo [3.2.2] nona-3,6,8-trien-2-one via thermal addition to bezyne

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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L Isakovic et al.
Organic letters, 3(26), 4189-4192 (2002-01-11)
The carbocyclic core of CP-225,917 and CP-263,114 is accessible through the [6+4] cycloaddition of a tropone with a 2-substituted cyclopentadiene. Examination of this reaction has revealed for the first time that this cycloaddition process is catalyzed by Lewis acids, including
Yuji Matsuya et al.
Organic letters, 11(6), 1361-1364 (2009-02-24)
Efficient synthesis of 3,4-diazabenzo[b]tropone was first achieved utilizing 4pi-8pi sequential electrocyclic reactions of functionalized benzocyclobutenone derivatives. These compounds are highly electron deficient and readily form amine adducts at ambient temperature. Furthermore, gentle heating resulted in quantitative nitrogen extrusion to produce
Y Nakagawa et al.
Chemico-biological interactions, 116(1-2), 45-60 (1999-01-07)
The mechanism of mitochondrial dysfunction and toxicity induced by the tropolones, beta-thujaplicin (4-isopropyl tropolone), tropolone and tropone, has been studied in freshly isolated rat hepatocytes. Incubation of hepatocytes with beta-thujaplicin (1-4 mM) elicited a concentration and time-dependent cell killing. The
Toxicity of microtubular drugs to leukemic lymphocytes.
R Schrek et al.
Experimental and molecular pathology, 34(3), 369-378 (1981-06-01)
Tohru Nishinaga et al.
Dalton transactions (Cambridge, England : 2003), 39(9), 2293-2300 (2010-02-18)
Heterotrinuclear Fe(II)-Cu(II)-Fe(II) complexes [Cu(FcTropOMe)(2)(H(2)O)(2)](OTf)(2) (FcTropOMe = 5-ferrocenyl-2-methoxytropone) (1), [Cu(FcTropNEt(2))(2)](OTf)(2) (FcTropNEt(2) = 2-(N,N-diethylamino)-5-ferrocenyltropone) (2) and [Cu(FcTropNEt)(2)] (FcTropNEt = 2-(N-ethylamino)-5-ferrocenyltroponate) (3) were synthesized. In addition, a hexafluorophosphate salt of heterotrinuclear Fe(III)-Cu(II)-Fe(III) complex [Cu(FcTropNEt)(2)](2+) (3(2+)) was successfully obtained as single crystals by electrochemical
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