Azulene

Azulene Basic information
Product Name:Azulene
Synonyms:AZULEN;AZULENE;BICYCLO(5.3.0)-DECA-1,3,5,7,9-PENTAENE;BICYCLO[5.3.0]DECAPENTAENE;LABOTEST-BB LT00007822;CYCLOPENTACYCLOHEPTEN;CYCLOPENTACYCLOHEPTENE;Azunamic
CAS:275-51-4
MF:C10H8
MW:128.17
EINECS:205-993-6
Product Categories:Aromatic Hydrocarbons (substituted) & Derivatives;Tropolones & Azulenes;Azulenes
Mol File:275-51-4.mol
Azulene Structure
Azulene Chemical Properties
Melting point 98-100 °C(lit.)
Boiling point 242 °C(lit.)
density 1.0530
refractive index 1.5736 (estimate)
Fp 241-243°C
storage temp. Store at +2°C to +8°C.
solubility Soluble in organic solvents.
form Fine Crystalline Powder
color Dark blue
Merck 14,926
BRN 969517
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKeyCUFNKYGDVFVPHO-UHFFFAOYSA-N
LogP3.200
CAS DataBase Reference275-51-4(CAS DataBase Reference)
EPA Substance Registry SystemAzulene (275-51-4)
Safety Information
Hazard Codes N
Risk Statements 51/53
Safety Statements 61
RIDADR UN 3077 9/PG 3
WGK Germany 2
RTECS CO4570000
8
TSCA Yes
HS Code 29029000
ToxicityLD50 orl-rat: >4 g/kg DRUGAY 6,13,82
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Azulene Usage And Synthesis
Chemical PropertiesAzulene is a blue crystalline compound with the chemical formula C10H8 and a melting point of 99°C. It contains afive-membered ring fused to a seven-membered ring and has aromatic properties. When heated it is converted into naphthalene.
Usesazulene 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!
UsesAzulene 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.
DefinitionChEBI: Azulene is a mancude carbobicyclic parent consisting of a cycloheptatriene and cyclopentadiene rings. It has a role as a plant metabolite and a volatile oil component. It is an ortho-fused bicyclic arene, a member of azulenes and a mancude carbobicyclic parent.
Synthesis Reference(s)Journal of the American Chemical Society, 75, p. 2386, 1953 DOI: 10.1021/ja01106a030
Tetrahedron Letters, 23, p. 495, 1982 DOI: 10.1016/S0040-4039(00)86871-9
Safety ProfilePoison by intraperitoneal,intravenous, and subcutaneous routes. When heated todecomposition it emits acrid smoke and irritating vapors.
SourceAzulene is a natural product and function as pigment in living organisms like plants, fungi etc. This compound was first isolated from the German Chamomile and later from yarrow, wormwood and other plants as oily liquid.
Purification MethodsCrystallise 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.]
Azulene Preparation Products And Raw materials
1,4-DIMETHYL-7-ISOPROPYLAZULENE-3-SULFONIC ACID RARECHEM AL BI 1110 5-ISOPROPYL-3,8-DIMETHYLAZULENE-1-CARBALDEHYDE LABOTEST-BB LT00007808 RARECHEM AL BM 1110 RARECHEM AL BF 1110 RARECHEM AL BZ 1084 DETERROL RARECHEM AL BD 1110 LABOTEST-BB LT00007807 RARECHEM AL BP 1110 LACTAROVIOLIN 4,6,8-TRIMETHYLAZULENE RARECHEM AL BK 1110 4-(IODOMETHYL)-AZULENE CHAMAZULEN 6-METHYLAZULENE RARECHEM AL BL 1084

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