azulene

• ChemBase ID: 108763
• Molecular Formular: C10H8
• Molecular Mass: 128.17052
• Monoisotopic Mass: 128.06260026
• SMILES: c1ccc2cccc2cc1
• Canonical SMILES: c1ccc2c(cc1)ccc2
• InChI: InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
• InChIKey: CUFNKYGDVFVPHO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: azulene
• IUPAC Traditional name: azulene
• Synonyms: AZULENE; Azulene; Bicyclo[5.3.0]decapentaene; 薁; 甘菊蓝; 奥甘菊环

Database IDs

• CAS Number: 275-51-4
• EC Number: 205-993-6
• MDL Number: MFCD00003810
• Beilstein Number: 969517
• Merck Index: 14926
• PubChem SID: 162094704; 24891490; 24863581
• PubChem CID: 9231
• CHEBI ID: 31249
• Chemspider ID: 8876
• KEGG ID: C13392
• Unique Ingredient Identifier: 82R6M9MGLP
• Wikipedia Title: Azulene

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.9627225
• LogD (pH = 7.4): 2.9627225
• Log P: 2.9627225
• Molar Refractivity: 42.5082 cm^3
• Polarizability: 18.077276 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.02 g/l in water
• Melting Point: 98-100 °C(lit.); 98-101°C; 99–100 °C; 99-100°C
• Boiling Point: 241-243°C; 242 °C; 242 °C(lit.); 242°C
• Std enthalpy of combustion: -1266.5 kcal/mol

Safety Information

• RTECS: CO4570000
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 51/53; R:36/37/38
• Safety Statements: 61; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS09
• GHS Hazard statements: H411
• GHS Precautionary statements: P273
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Product Information

• Purity: 99%
• Grade: analytical standard, for environmental analysis
• Empirical Formula (Hill Notation): C10H8

DETAILS

MP Biomedicals - 05208635

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A97203

Packaging
1 g in glass bottle
100 mg in glass bottle

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).