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

L08271 Azulene, 99%

CAS Number
275-51-4
Synonyms
Bicyclo[5.3.0]decapentaene

Size Price ($) Quantity Availability
250mg 59.12
1g 164.80
5g 599.46
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Azulene, 99%

MDL
MFCD00003810
EINECS
205-993-6

Chemical Properties

Formula
C10H8
Formula Weight
128.17
Melting point
98-101°
Boiling Point
241-243°
Solubility
Soluble in organic solvents.

Applications

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>.

Notes

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

Literature References

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.

Other References

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

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