275-51-4 Usage
Chemical Description
Azulene is a bicyclic aromatic hydrocarbon with a blue color and a characteristic odor.
Description
Azulene is a blue crystalline compound, C10H8, with a melting point of 99°C. It consists of a seven-membered ring fused to a five-membered ring and possesses aromatic properties. When heated, it converts into naphthalene. Azulene is a mancude carbobicyclic parent made up of a cycloheptatriene and cyclopentadiene rings.
Uses
Used in Cosmetics and Personal Care Industry:
Azulene is used as an additive in ointments, cosmetics, shaving creams, and other topical products. It serves as an active ingredient due to its anti-inflammatory, calming, and soothing properties, making it excellent for sensitive skin. However, caution is advised as it can cause staining.
Used in Pharmaceutical Industry:
Azulene is used as an anti-inflammatory, calming, and soothing agent in the pharmaceutical industry. It is derived from German chamomile and is known for its characteristic deep blue color.
Used in Chemical Industry:
Azulene is used as an antioxidant and is involved in anti-inflammatory activities. It is also used in the colorimetric determination of furfural.
Used in Organometallic Chemistry:
Azulene acts as a ligand for low-valent metals and forms pi complexes with both cyclopentadienyl and cycloheptatrienyl ligands in organometallic chemistry.
Used in Chemical Synthesis:
Azulene is used as a precursor for the preparation of (azulene)Mo2(CO)6 and (azulene)Fe2(CO)5 compounds.
Synthesis Reference(s)
Journal of the American Chemical Society, 75, p. 2386, 1953 DOI: 10.1021/ja01106a030Tetrahedron Letters, 23, p. 495, 1982 DOI: 10.1016/S0040-4039(00)86871-9
Safety Profile
Poison by intraperitoneal,intravenous, and subcutaneous routes. When heated todecomposition it emits acrid smoke and irritating vapors.
Purification Methods
Crystallise azulene from EtOH. It has UV max 270nm (log 4.72) in hexane. [Platner & Magyar Helv Chim Acta 25 581 1942, Beilstein 5 IV 1636.]
Check Digit Verification of cas no
The CAS Registry Mumber 275-51-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,7 and 5 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 275-51:
(5*2)+(4*7)+(3*5)+(2*5)+(1*1)=64
64 % 10 = 4
So 275-51-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
275-51-4Relevant articles and documents
A Convenient Synthesis of Azulene
Langhals, Heinz,Ebersp?cher, Moritz
, p. 1862 - 1866 (2018)
An improved and scalable synthesis of azulene has been developed by the application of pyrrolidine as a reagent and continuous steam distillation and extraction for workup. Applications for the coloration of perfluorinated media and silicones were demonstrated.
Plattner,Pfau
, p. 224,229 (1937)
Preparation of azulenyllithium and magnesium reagents utilizing halogen-metal exchange reaction of several iodoazulenes with organolithium or magnesium ate complex
Ito, Shunji,Kubo, Takahiro,Morita, Noboru,Matsui, Yoshitaka,Watanabe, Toshiyuki,Ohta, Akira,Fujimori, Kunihide,Murafuji, Toshihiro,Sugihara, Yoshikazu,Tajiri, Akio
, p. 2891 - 2894 (2004)
Preparation of several azulenyllithium and magnesium reagents was achieved by the halogen-metal exchange reaction of iodoazulenes with n-butyllithium or lithium tri(n-butyl)magnesate at low temperature and the synthetic application of the reagents was explored.
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Scott,L.T.
, p. 882 - 883 (1973)
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Coupling reaction of azulenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes with haloazulenes
Kurotobi, Kei,Tabata, Hiroshi,Miyauchi, Masato,Murafuji, Toshihiro,Sugihara, Yoshikazu
, p. 1013 - 1016 (2002)
In order to study the physicochemical properties of azulene oligomers, the synthesis and a coupling reaction of 2-(2-amino-1,3-bisethoxycarbonyl-6-azulenyl)-4,4,5,5-tetramethyl-1,3,2- dioxaborolane (1) and 2-(2-azulenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2) were examined.
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Kovats et al.
, p. 983 (1954)
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Prelog,Schenker
, p. 1181 (1953)
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Kovats et al.
, p. 2123 (1954)
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Gold-Catalyzed Direct Alkynylation of Azulenes
Székely, Anna,Péter, áron,Aradi, Klára,Tolnai, Gergely L.,Novák, Zoltán
, p. 954 - 957 (2017/02/26)
A novel catalytic method for the direct C-H alkynylation of azulenes is developed. The gold catalyzed functionalization of this special carbacycle is achieved with hypervalent iodonium reagent TIPS-EBX under mild reaction conditions. With the aid of the developed procedure, several TIPS alkynylated azulene derivatives were synthesized bearing important functional groups for further functionalization.