Azulene

Base Information

• Chemical Name: Azulene
• CAS No.: 275-51-4
• Molecular Formula: C10H8
• Molecular Weight: 128.174
• Hs Code.: 29029000
• European Community (EC) Number: 205-993-6
• NSC Number: 89248
• UNII: 82R6M9MGLP
• DSSTox Substance ID: DTXSID2059770
• Nikkaji Number: J39.308H
• Wikipedia: Azulene
• Wikidata: Q144362
• Metabolomics Workbench ID: 54363
• ChEMBL ID: CHEMBL3272628
• Mol file: 275-51-4.mol

Synonyms:Azulekeep;azulene;cyclopentacycloheptene

Chemical Property of Azulene

Chemical Property:

• Appearance/Colour: Blue Crystal
• Vapor Pressure: 0.165mmHg at 25°C
• Melting Point: 98-100 °C(lit.)
• Refractive Index: 1.632
• Boiling Point: 220.718 °C at 760 mmHg
• Flash Point: 76.66 °C
• PSA: 0.00000
• Density: 1.037 g/cm³
• LogP: 2.79140
• Storage Temp.: Store at +2°C to +8°C.
• Solubility.: Soluble in organic solvents.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 128.062600255
• Heavy Atom Count: 10
• Complexity: 94.6

Purity/Quality:

98%,99%, ^*data from raw suppliers

Azulene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C=CC=C2C=C1
• Recent NIPH Clinical Trials: Effect of tea gargling on periodontal tissue
• Uses: 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)Mo2 (CO)6 and (azulene)Fe2 (CO)5. azulene is renowned as an anti-inflammatory, calming, and soothing agent. excellent for sensitive skin, azulene is a german chamomile derivative with a characteristic deep blue color. Careful, it stains!

Technology Process of Azulene

There total 143 articles about Azulene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2-azulenyl trifluoromethanesulfonate (607393-61-3) → azulene (275-51-4)

Guidance literature:

With formic acid; tributyl-amine; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1,4-dioxane; for 24h; Heating;

DOI:10.1039/b212484j

Reference yield: 94.0%

6-(dimethylamino)fulvene (696-68-4) + (1R,2S,6R,7R)-3,3-Dioxo-3λ6-thia-tricyclo[5.2.2.02,6]undeca-4,8,10-triene-8,9-dicarboxylic acid dimethyl ester → phthalic acid dimethyl ester (131-11-3,64441-70-9) + azulene (275-51-4)

Guidance literature:

In 1,2-dichloro-ethane; for 44h; Product distribution; Heating;

DOI:10.1246/bcsj.72.1919

Reference yield: 92.0%

1-chloroazulene (23306-02-7) → azulene (275-51-4)

Guidance literature:

With potassium phosphate; poly(methylhydrosiloxane); palladium diacetate; In tetrahydrofuran; at 80 ℃; for 12h;

DOI:10.1002/anie.200501276

upstream raw materials:

cyclodecane

INDANE

bicyclo<5.3.0>decane

1,4,5,6,7,8-hexahydro-azulene

Downstream raw materials:

1,3-diiodoazulene

azulen-1-yl(phenyl)methanone

4-phenylazulene

N-azulen-1-yl-N'-trityl-hydrazine

Refernces

• 1、 Copland et al.. "". . p. 639. Retrieved 1977.
• 2、 Kr?mer, Guido,Detert, Heiner,Meier, Herbert. "Generation of hexahydroazulenes". . p. 4810 - 4812. Retrieved 2009.
• 3、 Kayushina, E. N.,Levin, D. Z.,Mortikov, E. S.,Promonenkov, V. K.. "PREPARATION OF AZULENE FROM COBALTOCENE". . p. 1931. Retrieved 1982.
• 4、 Murafuji, Toshihiro,Tasaki, Yusuke,Fujinaga, Masayuki,Tao, Keisuke,Kamijo, Shin,Ishiguro, Katsuya. "Blue Amino Acids Derived from Azulen-1-ylboronic Acid Pinacol Ester via the Petasis Reaction". . p. 1037 - 1042. Retrieved 2017.
• 5、 Doering et al.. "-". . p. 2386. Retrieved 1953.
• 6、 Ito, Shunji,Yokoyama, Ryuji,Okujima, Tetsuo,Terazono, Tomomi,Kubo, Takahiro,Tajiri, Akio,Watanabe, Masataka,Morita, Noboru. "Reaction of azulenes with 1-trifluoromethanesulfonylpyridinium trifluoromethanesulfonate (TPT) and synthesis of the parent azulene.". . p. 1947 - 1952. Retrieved 2003.
• 7、 Jost, P.,Chaquin, P.,Kossanyi, J.. "UNE NOUVELLE VOIE D'ACCES AU SQUELETTE DE L'AZULENE". . p. 465 - 466. Retrieved 1980.
• 8、 Ishikawa, Hiroyuki,Nishida, Jun-Ichi,Jones, John W.,Scott, Lawrence T.,Kawase, Takeshi. "Bicyclo[6.3.0]undeca-1(11),2,4,6,8-pentaen-10-ylidene: An Aromatic Carbene with Ambiphilic Properties". . p. 1073 - 1077. Retrieved 2017/07/25.