Azulene

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  • Identifiers

    CAS number
    275-51-4

    Molecular formula
    C10H8

    SMILES
    C1=CC=C2C=CC=C2C=C1

    Safety labels

    Environmental Hazard
    Environmental

    Retention indicies (RI)

    • DB5: 1299.0
    • Carbowax: 1706.0

  • Odor profile

    Pungent 58.71%
    Green 58.02%
    Geranium 57.86%
    Rose 57.46%
    Metallic 57.17%
    Camphoreous 45.02%
    Earthy 36.53%
    Sweet 35.25%
    Floral 31.67%
    Dry 30.73%

    Scent© AI

  • Properties

    XLogP3-AA
    3.2

    Molecular weight
    128.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    218°C

    Flash point est.
    74.63 ˚C

  • Synonyms

    • azulene
    • 275-51-4
    • Cyclopentacycloheptene
    • Azunamic
    • Bicyclo[5.3.0]decapentaene
    • azulen
    • Bicyclo(5.3.0)decapentaene
    • EINECS 205-993-6
    • UNII-82R6M9MGLP
    • 82R6M9MGLP
    • Bicyclo(5.3.0)-1,3,5,7,9-decapentaene
    • MFCD00003810
    • NSC 89248
    • Azulene (JAN)
    • Bicyclo(5.3.0)-deca-2,4,6,8,10-pentaene
    • CHEBI:31249
    • AZULENE [JAN]
    • AZULENE [MI]
    • AZULENE [MART.]
    • NSC-89248
    • AZULENE [WHO-DD]
    • Azusalen [as sodium sulfonate]
    • DTXSID2059770
    • AZULENE (MART.)
    • Bicyclo(0.3.5)deca-1,3,5,7,9-pentaene
    • Azusalen (as sodium sulfonate)
    • BICYCLO-(0.3.5)-DECA-1,3,5,7,9-PENTAENE
    • BICYCLO-(5.3.0)-DECA-2,4,6,8,10-PENTAENE
    • Azulekeep
    • Azulene (Standard)
    • Azulene, 99%
    • AZULENE [INCI]
    • Azulene, analytical standard
    • CHEMBL3272628
    • DTXCID7037686
    • HY-B0055R
    • HY-B0055
    • NSC89248
    • AKOS015840881
    • FC66428
    • CS-15638
    • Bicyclo[5.3.0]-1,5,7,9-decapentaene
    • DB-047243
    • A0634
    • CS-0006517
    • NS00013373
    • Azulene, standard for GC, >=99.0% (GC)
    • bicyclo[5.3.0]deca-2,4,6,8,10-pentaene
    • C13408
    • D09768
    • A819116
    • Q144362
    • SR-01000944574
    • SR-01000944574-1
    • 205-993-6

  • Applications

    Azulene (CAS 275-51-4) is a deep-blue nonbenzenoid aromatic hydrocarbon used in: (1) optoelectronic materials, as a donor/acceptor unit in π-conjugated polymers and small molecules for OLEDs, OPVs, OFETs, near-IR absorbers and nonlinear optical media owing to its large dipole, unusual HOMO/LUMO topology and S2 fluorescence; (2) sensing and displays, as a pH/polarity-responsive probe, color-changing indicator inks, anti-counterfeiting tags and redox-switchable motifs; (3) cosmetics and practical colorants, serving as a precursor/scaffold for azulene derivatives (e.g., guaiazulene, chamazulene) valued for skin-soothing, anti-redness effects and blue hue; (4) fundamental and synthetic chemistry, as a benchmark molecule for nonalternant aromaticity in teaching and spectroscopy/computation, and as a building block functionalized at the 1,3-positions to access reagents, ligands, metal complexes and supramolecular architectures.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 163.02
    methanol 164.61
    isopropanol 126.25
    water 0.74
    ethyl acetate 632.12
    n-propanol 157.52
    acetone 775.69
    n-butanol 169.04
    acetonitrile 516.23
    DMF 1044.87
    toluene 481.99
    isobutanol 129.6
    1,4-dioxane 2051.21
    methyl acetate 577.69
    THF 1508.72
    2-butanone 581.85
    n-pentanol 172.42
    sec-butanol 130.71
    n-hexane 207.75
    ethylene glycol 46.21
    NMP 1127.25
    cyclohexane 217.01
    DMSO 954.71
    n-butyl acetate 774.33
    n-octanol 176.27
    chloroform 1394.23
    n-propyl acetate 652.06
    acetic acid 250.56
    dichloromethane 1708.57
    cyclohexanone 1131.73
    propylene glycol 45.72
    isopropyl acetate 477.45
    DMAc 627.8
    2-ethoxyethanol 303.76
    isopentanol 177.65
    n-heptane 156.31
    ethyl formate 387.67
    1,2-dichloroethane 1242.06
    n-hexanol 245.81
    2-methoxyethanol 353.84
    isobutyl acetate 528.56
    tetrachloromethane 360.46
    n-pentyl acetate 399.82
    transcutol 1210.01
    n-heptanol 146.8
    ethylbenzene 383.88
    MIBK 438.85
    2-propoxyethanol 415.94
    tert-butanol 195.64
    MTBE 378.37
    2-butoxyethanol 278.84
    propionic acid 229.62
    o-xylene 292.03
    formic acid 54.28
    diethyl ether 657.77
    m-xylene 315.7
    p-xylene 423.35
    chlorobenzene 625.87
    dimethyl carbonate 383.44
    n-octane 81.86
    formamide 139.14
    cyclopentanone 1339.39
    2-pentanone 550.58
    anisole 752.44
    cyclopentyl methyl ether 836.11
    gamma-butyrolactone 1318.19
    1-methoxy-2-propanol 282.55
    pyridine 1060.28
    3-pentanone 529.95
    furfural 988.18
    n-dodecane 62.38
    diethylene glycol 233.69
    diisopropyl ether 289.99
    tert-amyl alcohol 168.87
    acetylacetone 854.78
    n-hexadecane 72.45
    acetophenone 564.02
    methyl propionate 485.15
    isopentyl acetate 601.27
    trichloroethylene 1719.85
    n-nonanol 173.78
    cyclohexanol 232.7
    benzyl alcohol 277.82
    2-ethylhexanol 242.76
    isooctanol 147.84
    dipropyl ether 641.59
    1,2-dichlorobenzene 575.93
    ethyl lactate 200.01
    propylene carbonate 728.76
    n-methylformamide 344.94
    2-pentanol 149.62
    n-pentane 104.69
    1-propoxy-2-propanol 343.88
    1-methoxy-2-propyl acetate 532.87
    2-(2-methoxypropoxy) propanol 328.35
    mesitylene 246.59
    ε-caprolactone 946.25
    p-cymene 197.12
    epichlorohydrin 1489.89
    1,1,1-trichloroethane 1036.94
    2-aminoethanol 78.19
    morpholine-4-carbaldehyde 1376.58
    sulfolane 1507.23
    2,2,4-trimethylpentane 59.63
    2-methyltetrahydrofuran 1059.06
    n-hexyl acetate 518.97
    isooctane 66.07
    2-(2-butoxyethoxy)ethanol 435.82
    sec-butyl acetate 469.26
    tert-butyl acetate 553.76
    decalin 163.74
    glycerin 90.73
    diglyme 1101.16
    acrylic acid 222.32
    isopropyl myristate 298.35
    n-butyric acid 342.37
    acetyl acetate 539.23
    di(2-ethylhexyl) phthalate 165.19
    ethyl propionate 585.93
    nitromethane 757.32
    1,2-diethoxyethane 876.2
    benzonitrile 467.37
    trioctyl phosphate 144.46
    1-bromopropane 619.18
    gamma-valerolactone 1399.22
    n-decanol 146.23
    triethyl phosphate 267.15
    4-methyl-2-pentanol 128.74
    propionitrile 404.01
    vinylene carbonate 722.57
    1,1,2-trichlorotrifluoroethane 560.98
    DMS 606.95
    cumene 257.05
    2-octanol 129.04
    2-hexanone 622.27
    octyl acetate 304.79
    limonene 287.37
    1,2-dimethoxyethane 1070.01
    ethyl orthosilicate 248.83
    tributyl phosphate 191.21
    diacetone alcohol 378.73
    N,N-dimethylaniline 463.11
    acrylonitrile 506.07
    aniline 347.2
    1,3-propanediol 136.55
    bromobenzene 762.51
    dibromomethane 1102.14
    1,1,2,2-tetrachloroethane 1190.6
    2-methyl-cyclohexyl acetate 435.5
    tetrabutyl urea 266.63
    diisobutyl methanol 192.65
    2-phenylethanol 308.73
    styrene 494.02
    dioctyl adipate 360.04
    dimethyl sulfate 563.04
    ethyl butyrate 662.98
    methyl lactate 190.82
    butyl lactate 202.98
    diethyl carbonate 428.68
    propanediol butyl ether 185.77
    triethyl orthoformate 408.85
    p-tert-butyltoluene 193.62
    methyl 4-tert-butylbenzoate 402.74
    morpholine 1220.24
    tert-butylamine 154.27
    n-dodecanol 131.09
    dimethoxymethane 787.5
    ethylene carbonate 654.88
    cyrene 324.32
    2-ethoxyethyl acetate 524.86
    2-ethylhexyl acetate 543.84
    1,2,4-trichlorobenzene 622.67
    4-methylpyridine 916.08
    dibutyl ether 543.18
    2,6-dimethyl-4-heptanol 192.65
    DEF 749.62
    dimethyl isosorbide 761.99
    tetrachloroethylene 883.47
    eugenol 334.28
    triacetin 440.81
    span 80 265.77
    1,4-butanediol 77.35
    1,1-dichloroethane 836.7
    2-methyl-1-pentanol 185.34
    methyl formate 354.41
    2-methyl-1-butanol 156.93
    n-decane 96.68
    butyronitrile 386.96
    3,7-dimethyl-1-octanol 203.56
    1-chlorooctane 276.16
    1-chlorotetradecane 133.73
    n-nonane 99.59
    undecane 75.0
    tert-butylcyclohexane 150.67
    cyclooctane 118.51
    cyclopentanol 270.76
    tetrahydropyran 1105.93
    tert-amyl methyl ether 325.21
    2,5,8-trioxanonane 699.39
    1-hexene 405.65
    2-isopropoxyethanol 268.24
    2,2,2-trifluoroethanol 123.66
    methyl butyrate 708.0

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Santolina chamaecyparisus (France) 2 84961-58-0 Santolina chamaecyparisus L., fam. Asteraceae (Compositae) 0.06%
Artemisia macrocephala (China) Artemisia macrocephala Jacq. ex Bess., fam. Asteraceae (Compositae) 0.97%
Michelia yunnanensis flower headspace (China) Michelia yunnanensis Franch. ex Finet et Gagnep., fam. Magnoliaceae 0.45%
Cymbidium sinense flower headspace (China) Cymbidium sinense (Andr.) Willd., fam. Orchidaceae 0.14%
Dendrobium chrysatoxum flower (China) Dendrobium chrysatoxum Lindl., fam. Orchidaceae 2.75%
Aglaia duperreana flower (China) Aglaia duperreana Pierre, fam. Meliaceae 0.22%