Tropolone Struktur

2-Hydroxycyclohepta-2,4,6-trienon

Bezeichnung:2-Hydroxycyclohepta-2,4,6-trienon

CAS-Nr533-75-5

Englisch Name:Tropolone

CBNumberCB7686256

SummenformelC7H6O2

Molgewicht122.12

MOL-Datei533-75-5.mol

Synonyma

2-Hydroxycyclohepta-2,4,6-trienon

2-Hydroxycyclohepta-2,4,6-trienon physikalisch-chemischer Eigenschaften

Schmelzpunkt	50-52 °C (lit.)
Siedepunkt	80-84 °C/0.1 mmHg (lit.)
Dichte	1.1483 (rough estimate)
Dampfdruck	3.4Pa at 25℃
Brechungsindex	1.5286 (estimate)
Flammpunkt	>230 °F
storage temp.	2-8°C
Löslichkeit	40.9g/l (experimental)
pka	6.7(at 25℃)
Aggregatzustand	Crystalline Powder
Farbe	Off-white to cream-beige
Wasserlöslichkeit	Soluble in water.
Sensitive	Hygroscopic
BRN	1904978
LogP	1.58 at 23℃
CAS Datenbank	533-75-5(CAS DataBase Reference)
NIST chemische Informationen	2,4,6-Cycloheptatrien-1-one, 2-hydroxy-(533-75-5)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	22-36/37/38-37/38-41
S-Sätze:	22-24/25-36/37/39-36-26
WGK Germany	3
RTECS-Nr.	GU4075000
F	8-10-23
HS Code	29144090

Gefahreninformationscode (GHS)

Tropolone Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R37/38:Reizt die Atmungsorgane und die Haut.
R41:Gefahr ernster Augenschäden.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
White to light yellow crystalline
Verwenden
Tropolone is a sensitive reagent for reducing sugars. A non-benzenoid aromatic compound, Reagent for the preparation of fused heterocycles and complexes of Ga(III) and In(III).
Verwenden
Reagent for the preparation of fused heterocycles1 and complexes of Ga(III) and In(III).2 Used as medicine and dye intermediates.
Definition
ChEBI: Tropolone is a cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii. It has a role as a bacterial metabolite, a toxin and a fungicide. It is a cyclic ketone, an enol and an alpha-hydroxy ketone. It derives from a hydride of a cyclohepta-1,3,5-triene.
Flammability and Explosibility
Not classified
Synthese
To a mixture of sodium hydroxide (33 g) with glacial acetic acid (270 ml) was added dropwise via funnel 7,7-dichlorobicyclo[3,2,0]hepta-2-ene-6-ketone (33.5 g) under nitrogen, and the mixture was heated to reflux for 8 hours. After PH was adjusted to 1 with hydrochloric acid (50 ml), the mixture was filtered and extracted with benzene (3 × 90ml). The combined extracts were concentrated in vacuo to give brownish black oil.Fraction of reduced pressure distillation at 100 °C/67 Pa was collected to give gross product as a pale yellow solid. Recrystallization from mixture of dichloromethane and pentane (1/4, V/V) gave analytically pure product Tropolone(17.8 g,77%) as a white needle crystal, m.p. 50~51 °C.
läuterung methode
Crystallise tropolone from hexane or pet ether and sublime it at 40o/4mm. Also distil it at high vacuum. [Beilstein 8 IV 159.]
structure and hydrogen bonding
The tropolone has a simple structure consisting of a seven-membered carbon ring. The pi electrons present in the ring are delocalised. A ketone grouped to the first carbon, and an hydroxyl group attached to the second carbon. Tropolone, C7H6O2, crystallizes in space group P21/c, with a = 7.135, b = 12.178, c = 7.122Å, β = 99.63 ° and Z = 4. The molecule is essentially planar and exhibits slight bond alternation in the seven-membered ring. The hydroxyl group makes a bifurcated hydrogen bond with carbonyl oxygen atoms, of which one branch is intramolecular and the other intermolecular. The latter intermolecular branches form a hydrogen-bonded dimer. These characteristic hydrogen bonds seem to play a role in increasing the contribution from the dipolar ionic forms to the ground state of the tropolone molecule.

Tropolone Upstream-Materialien And Downstream Produkte

2-Hydroxycyclohepta-2,4,6-trienon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

533-75-5, Tropolone Verwandte Suche:

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