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252832

Sigma-Aldrich

Tropone

97%

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Synonym(s):
2,4,6-Cycloheptatrien-1-one
Empirical Formula (Hill Notation):
C7H6O
CAS Number:
Molecular Weight:
106.12
Beilstein:
1902335
EC Number:
MDL number:
PubChem Substance ID:
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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1 of 4

This Item
T89702108637161241
Tropone 97%

Sigma-Aldrich

252832

Tropone

Tropolone 98%

Sigma-Aldrich

T89702

Tropolone

Tropolone EMPROVE® EVOLVE

SAFC

108637

Tropolone

1-Phenyl-1-propyne 99%

Sigma-Aldrich

161241

1-Phenyl-1-propyne

form

liquid

form

-

form

-

form

liquid

refractive index

n20/D 1.615 (lit.)

refractive index

-

refractive index

-

refractive index

n20/D 1.564 (lit.)

bp

113 °C/15 mmHg (lit.)

bp

80-84 °C/0.1 mmHg (lit.)

bp

80-84 °C/0.1 mmHg (lit.)

bp

185 °C (lit.)

density

1.094 g/mL at 25 °C (lit.)

density

-

density

-

density

0.928 g/mL at 25 °C (lit.)

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

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

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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
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
Barry M Trost et al.
Journal of the American Chemical Society, 130(45), 14960-14961 (2008-10-22)
The cyanosubstituted trimethylenemethane donor undergoes palladium-catalyzed [6 + 3] cycloaddition with a variety of tropones to yield bicyclo[4.3.1]decadienes in excellent regio-, diastereo-, and enantioselectivity. Products of the Pd-TMM [6 + 3] cycloaddition participate in a thermal [3,3] sigmatropic rearrangement to

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