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275-51-4 - Azulene, 99% - Bicyclo[5.3.0]decapentaene - L08271 - Alfa Aesar

L08271 Azulene, 99%

CAS-Nummer
275-51-4
Synonyme
Bicyclo[5.3.0]decapentaene

Größe Preis ($) Menge Verfügbarkeit
250mg 59,12
1g 164,80
5g 599,46
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

Azulene, 99%

MDL
MFCD00003810
EINECS
205-993-6

Chemische Eigenschaften

Formel
C10H8
Molmasse
128.17
Schmelzpunkt
98-101°
Siedepunkt
241-243°
Löslichkeit
Soluble in organic solvents.

Anwendungen

Azulene is used as an additive in ointments. It is an active ingredient in cosmetics, shaving creams and other topicals. It is used as antioxidant and in anti-inflammatory activities. It is involved in the colorimetric determination of furfural. It acts as ligand for low valent metals and forms pi complexes with both cyclopentadienyl and cylcloheptatrienyl ligands in organometallic chemistry. It is also used as precursor for the preparation of (azulene)Mo<sub>2</sub> (CO)<sub>6</sub> and (azulene)Fe<sub>2</sub> (CO)<sub>5</sub>.

Bemerkungen

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.

Literaturverweise

Interesting non-alternant hydrocarbon, isoelectronic with naphthalene.

Readily undergoes electrophilic substitution at the 1-position of the five-membered ring; e.g. formylation with triethyl orthoformate and boron trifluoride etherate: Tetrahedron Lett ., 4707 (1967), and Friedel-Crafts acylation without a catalyst, using either trichloro- or trifluoroacetic anhydride: J. Org. Chem., 27, 3578 (1962).

Nucleophilic substitution occurs at the 4- and 6-positions of the 7-membered ring: Liebigs Ann. Chem., 1222 (1986). For a review of azulene chemistry, see: Russ. Chem. Rev., 46, 530 (1977).

Shao, J.; Korendovych, I. V.; Broos, J. Biosynthetic incorporation of the azulene moiety in proteins with high efficiency. Amino Acids 2015, 47 (1), 213-216.

Tang, T.; Lin, T.; Wang, F.; He. C. Origin of Near-Infrared Absorption for Azulene-Containing Conjugated Polymers upon Protonation or Oxidation. J. Phys. Chem. B 2015, 119 (25), 8176-8183.

Weitere Referenzen

Merck
14,926
Beilstein
969517
Harmonized Tariff Code
2902.19
TSCA
Yes
RTECS
CO4570000

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