Quinoline

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  • Identifiers

    CAS number
    91-22-5

    Molecular formula
    C9H7N

    SMILES
    C1=CC=C2C(=C1)C=CC=N2

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Sweet 81.8%
    Animal 61.79%
    Tobacco 60.23%
    Musty 53.02%
    Earthy 48.43%
    Herbal 48.2%
    Burnt 44.85%
    Leathery 42.91%
    Phenolic 41.73%
    Pungent 41.51%

     

    Flavor
    Tobacco 54.58%
    Herbal 43.78%
    Musty 42.55%
    Nutty 41.94%
    Sweet 41.38%
    Earthy 41.31%
    Fecal 40.45%
    Rubber 38.77%
    Fishy 36.14%
    Balsam 33.83%

     

    Odor impact est.
    High

    Odor threshold

    • Odor Threshold Low: 71.0 [mmHg]. [ICSC] Odor threshold from HSDB
    • 71 PPM

  • Properties

    XLogP3-AA
    2.0

    pKa est.
    4.7 (weak acid)

    Molecular weight
    129.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Melting point expt.

    • 5 °F (NTP, 1992)
    • -14.78 °C
    • -15.6 °C
    • -15 °C

    Boiling point

    • 460 °F at 760 mmHg (NTP, 1992)
    • 237.7 °C @ 760 mm Hg
    • 239.00 °C. @ 760.00 mm Hg
    • 238 °C

    Flash point

    • 90.95 ˚C est.
    • 138 °F (NFPA, 2010)
    • 105 °C
    • 99 °C, (Closed Cup)
    • 101 °C c.c.

    Solubility expt.

    • 12.4 [ug/mL] (The mean of the results at pH 7.4)
    • less than 0.1 mg/mL at 72.5 °F (NTP, 1992)
    • Soluble in alcohol, ether, and carbon disulfide
    • Miscible with oxygenated solvents
    • More sol in hot than cold water; sol in ethanol, ethyl ether, acetone, carbon disulfide and other common organic solvents.
    • In water, 6,110 mg/l @ 25 °C
    • 6.11 mg/mL at 25 °C
    • Solubility in water, g/100ml at 20 °C: 0.61 (very poor)

  • Synonyms

    • QUINOLINE
    • 91-22-5
    • 1-Benzazine
    • 1-Azanaphthalene
    • Chinolin
    • Chinoleine
    • Chinoline
    • Quinolin
    • Leucol
    • Leukol
    • Benzopyridine
    • 2,3-Benzopyridine
    • Benzo(b)pyridine
    • Benzo[b]pyridine
    • Quinoline-3-D
    • Quinoline-4-D
    • Quinoline-5-D
    • Quinoline-6-D
    • Quinoline-7-D
    • USAF EK-218
    • Quinoline-8-D
    • 1-Benzine
    • FEMA No. 3470
    • B 500
    • CCRIS 547
    • NSC 3396
    • HSDB 121
    • DTXSID1021798
    • CHEBI:17362
    • Quinoline (8CI,9CI)
    • AI3-01241
    • B-500
    • EINECS 202-051-6
    • UNII-E66400VT9R
    • E66400VT9R
    • NSC-3396
    • CHEMBL14474
    • DTXCID401798
    • 15793-82-5
    • 15793-83-6
    • 15793-84-7
    • 15793-85-8
    • 15793-86-9
    • EC 202-051-6
    • 15793-87-0
    • QUINOLINE (IARC)
    • QUINOLINE [IARC]
    • Chinolin [Czech]
    • Benzopyridine (VAN)
    • Quinoline-
    • CAS-91-22-5
    • UN2656
    • hydroquinoline
    • 4-quinolinyl
    • 1-Benzazene
    • Quinoline [UN2656] [Poison]
    • MFCD00006736
    • MFCD31699982
    • MFCD31699983
    • MFCD31699984
    • MFCD31699985
    • MFCD31699986
    • MFCD31699987
    • 1-AZANAPTHALENE
    • Quinoline, >=97%
    • Quinoline, >=99%
    • QUINOLINE [MI]
    • QUINOLINE [FHFI]
    • QUINOLINE [HSDB]
    • Quinoline > 90% grade
    • Epitope ID:140096
    • BENZO (B) PYRIDINE
    • SCHEMBL2774
    • NCIOpen2_007906
    • WLN: T66 BNJ
    • MLS002303065
    • BIDD:ER0666
    • Quinoline, analytical standard
    • SCHEMBL483852
    • SCHEMBL1193639
    • SCHEMBL3311562
    • SCHEMBL8571823
    • Quinoline, reagent grade, 96%
    • Quinoline, reagent grade, 98%
    • FEMA 3470
    • NSC3396
    • Quinoline, redistilled from glass
    • DTXSID301317900
    • HMS2271F08
    • Quinoline [UN2656] [Poison]
    • Quinoline, for synthesis, 96.0%
    • STR01546
    • Tox21_201478
    • Tox21_300068
    • BBL011390
    • BDBM50047015
    • s6369
    • STL146493
    • Quinoline 500 microg/mL in Methanol
    • AKOS000119139
    • UN 2656
    • NCGC00091190-01
    • NCGC00091190-02
    • NCGC00091190-03
    • NCGC00091190-04
    • NCGC00254119-01
    • NCGC00259029-01
    • Quinoline, SAJ first grade, >=94.0%
    • SMR000112309
    • SY246281
    • SY246329
    • SY246330
    • SY246331
    • SY246332
    • SY246333
    • Quinoline, JIS special grade, >=95.0%
    • DB-057248
    • NS00010850
    • Q0011
    • Q0085
    • EN300-19120
    • C06413
    • D97671
    • AE-641/01960007
    • Q408384
    • F0001-2218
    • Z104472852
    • InChI=1/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7

  • Applications

    Quinoline (CAS 91-22-5) is a nitrogen-containing aromatic heterocycle widely used as an intermediate to produce 8‑hydroxyquinoline (oxine) and numerous derivatives for metal chelation in extraction, analytical reagents, preservation, and antifungal uses; it serves as a key medicinal scaffold (4‑/8‑aminoquinoline antimalarials and various antibacterial, antiviral, and anticancer agents), in agrochemicals (fungicides, insecticides, herbicides), and in dyes and pigments (e.g., quinophthalone systems such as Quinoline Yellow and fluorescent/cyanine dyes); it is employed in materials science to form organometallic complexes like Alq3 for OLEDs and other emissive/conductive materials; used as a solvent/reaction medium for resins, tar, and terpenes and to determine “quinoline insolubles” in pitch; and functions as a precursor to corrosion inhibitors and petroleum additives, as well as a research building block in organic synthesis, catalysis, photocatalysis, and metal-ion sensing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 143.81
    methanol 111.4
    isopropanol 120.98
    water 1.31
    ethyl acetate 385.09
    n-propanol 140.45
    acetone 506.26
    n-butanol 144.13
    acetonitrile 363.55
    DMF 518.48
    toluene 227.96
    isobutanol 120.41
    1,4-dioxane 1189.43
    methyl acetate 350.14
    THF 757.17
    2-butanone 385.46
    n-pentanol 149.99
    sec-butanol 122.13
    n-hexane 80.3
    ethylene glycol 30.91
    NMP 490.57
    cyclohexane 65.92
    DMSO 737.52
    n-butyl acetate 418.49
    n-octanol 103.96
    chloroform 819.28
    n-propyl acetate 406.55
    acetic acid 213.53
    dichloromethane 1125.67
    cyclohexanone 561.67
    propylene glycol 23.93
    isopropyl acetate 225.08
    DMAc 338.57
    2-ethoxyethanol 235.18
    isopentanol 138.56
    n-heptane 61.12
    ethyl formate 242.02
    1,2-dichloroethane 779.3
    n-hexanol 173.24
    2-methoxyethanol 262.31
    isobutyl acetate 277.23
    tetrachloromethane 176.61
    n-pentyl acetate 215.48
    transcutol 927.21
    n-heptanol 97.81
    ethylbenzene 159.97
    MIBK 215.35
    2-propoxyethanol 276.51
    tert-butanol 153.34
    MTBE 212.83
    2-butoxyethanol 183.28
    propionic acid 161.42
    o-xylene 133.99
    formic acid 47.06
    diethyl ether 386.36
    m-xylene 141.31
    p-xylene 195.8
    chlorobenzene 300.82
    dimethyl carbonate 153.63
    n-octane 34.24
    formamide 114.47
    cyclopentanone 638.57
    2-pentanone 316.08
    anisole 313.05
    cyclopentyl methyl ether 380.19
    gamma-butyrolactone 705.74
    1-methoxy-2-propanol 181.16
    pyridine 627.44
    3-pentanone 281.95
    furfural 561.19
    n-dodecane 24.9
    diethylene glycol 172.08
    diisopropyl ether 116.93
    tert-amyl alcohol 132.5
    acetylacetone 393.04
    n-hexadecane 28.57
    acetophenone 251.53
    methyl propionate 263.35
    isopentyl acetate 284.78
    trichloroethylene 1070.23
    n-nonanol 97.35
    cyclohexanol 151.71
    benzyl alcohol 159.03
    2-ethylhexanol 132.73
    isooctanol 89.21
    dipropyl ether 270.76
    1,2-dichlorobenzene 249.68
    ethyl lactate 105.9
    propylene carbonate 349.44
    n-methylformamide 220.16
    2-pentanol 111.07
    n-pentane 48.4
    1-propoxy-2-propanol 205.0
    1-methoxy-2-propyl acetate 237.73
    2-(2-methoxypropoxy) propanol 166.11
    mesitylene 92.39
    ε-caprolactone 494.83
    p-cymene 87.34
    epichlorohydrin 941.07
    1,1,1-trichloroethane 509.59
    2-aminoethanol 59.51
    morpholine-4-carbaldehyde 636.28
    sulfolane 708.38
    2,2,4-trimethylpentane 25.15
    2-methyltetrahydrofuran 573.58
    n-hexyl acetate 264.81
    isooctane 23.9
    2-(2-butoxyethoxy)ethanol 251.47
    sec-butyl acetate 225.51
    tert-butyl acetate 213.97
    decalin 49.4
    glycerin 52.12
    diglyme 556.01
    acrylic acid 141.68
    isopropyl myristate 113.56
    n-butyric acid 236.23
    acetyl acetate 228.85
    di(2-ethylhexyl) phthalate 76.08
    ethyl propionate 285.51
    nitromethane 525.23
    1,2-diethoxyethane 479.51
    benzonitrile 265.91
    trioctyl phosphate 65.18
    1-bromopropane 392.31
    gamma-valerolactone 752.87
    n-decanol 79.84
    triethyl phosphate 106.57
    4-methyl-2-pentanol 79.56
    propionitrile 278.05
    vinylene carbonate 342.28
    1,1,2-trichlorotrifluoroethane 303.2
    DMS 240.63
    cumene 106.73
    2-octanol 79.21
    2-hexanone 376.75
    octyl acetate 133.33
    limonene 120.96
    1,2-dimethoxyethane 675.35
    ethyl orthosilicate 101.67
    tributyl phosphate 88.17
    diacetone alcohol 189.24
    N,N-dimethylaniline 184.47
    acrylonitrile 327.1
    aniline 197.35
    1,3-propanediol 111.73
    bromobenzene 352.36
    dibromomethane 712.58
    1,1,2,2-tetrachloroethane 648.95
    2-methyl-cyclohexyl acetate 171.5
    tetrabutyl urea 116.94
    diisobutyl methanol 87.71
    2-phenylethanol 160.77
    styrene 194.64
    dioctyl adipate 139.62
    dimethyl sulfate 228.37
    ethyl butyrate 285.71
    methyl lactate 85.56
    butyl lactate 124.6
    diethyl carbonate 175.17
    propanediol butyl ether 123.69
    triethyl orthoformate 160.35
    p-tert-butyltoluene 79.94
    methyl 4-tert-butylbenzoate 162.44
    morpholine 743.56
    tert-butylamine 110.36
    n-dodecanol 66.93
    dimethoxymethane 386.46
    ethylene carbonate 318.53
    cyrene 154.89
    2-ethoxyethyl acetate 291.35
    2-ethylhexyl acetate 248.86
    1,2,4-trichlorobenzene 281.1
    4-methylpyridine 531.46
    dibutyl ether 262.82
    2,6-dimethyl-4-heptanol 87.71
    DEF 374.41
    dimethyl isosorbide 327.16
    tetrachloroethylene 516.26
    eugenol 166.77
    triacetin 204.51
    span 80 126.44
    1,4-butanediol 62.82
    1,1-dichloroethane 524.67
    2-methyl-1-pentanol 138.67
    methyl formate 215.97
    2-methyl-1-butanol 130.66
    n-decane 39.2
    butyronitrile 266.76
    3,7-dimethyl-1-octanol 105.35
    1-chlorooctane 124.96
    1-chlorotetradecane 55.55
    n-nonane 40.6
    undecane 30.34
    tert-butylcyclohexane 47.58
    cyclooctane 31.88
    cyclopentanol 171.48
    tetrahydropyran 655.09
    tert-amyl methyl ether 168.48
    2,5,8-trioxanonane 326.34
    1-hexene 200.76
    2-isopropoxyethanol 192.25
    2,2,2-trifluoroethanol 96.66
    methyl butyrate 389.02

    Scent© AI

1 4

IFRA standard 51

Recommendation
Prohibition
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0 %
Category 2
Products applied to the axillae
 0 % Category 7B
Leave-on products applied to the hair with some hand contact
 0 %
Category 3
Products applied to the face/body using fingertips
 0 % Category 8
Products with significant anogenital exposure
 0 %
Category 4
Products related to fine fragrance
 0 % Category 9
Products with body and hand exposure, primarily rinse off
 0 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0 % Category 10A
Household care products with mostly hand contact
 0 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 0 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 0 %
Category 5D
Baby Creams, baby Oils and baby talc
 0 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0 %
Category 6
Products with oral and lip exposure
 0 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 0 %

Prohibition
Quinoline should not be used as a fragrance ingredient.

Botanical

Name CAS Botanical Proportion
Orris butter 8002-73-1 Iris florentina L., fam. Iridaceae 0.01%
Osmanthus concentrate 1 (Sukhumi-Abkhasia) 68917-05-5 Osmanthus fragrans (Thunb.) Lour., fam. Oleaceae 0.05%
Osmanthus concentrate 2 (Sukhumi-Abkhasia) 68917-05-5 Osmanthus fragrans (Thunb.) Lour., fam. Oleaceae 0.03%