Benzofuran

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  • Identifiers

    CAS number
    271-89-6

    Molecular formula
    C8H6O

    SMILES
    C1=CC=C2C(=C1)C=CO2

    Safety labels

    Flammable
    Flammable

    Health Hazard
    Health

  • Odor profile

    Sweet 66.19%
    Burnt 62.36%
    Pungent 51.1%
    Phenolic 46.6%
    Ethereal 44.3%
    Musty 38.53%
    Smoky 38.45%
    Medicinal 33.79%
    Earthy 33.55%
    Aromatic 31.55%

    Scent© AI

  • Properties

    XLogP3-AA
    2.7

    Molecular weight
    118.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Melting point expt.

    • less than -0.4 °F (NTP, 1992)
    • Less than -18 °C
    • < -18 °C

    Boiling point

    • 345 °F at 760 mmHg (NTP, 1992)
    • 174 °C @ 760 mm Hg
    • BP: 62-63 °C @ 15 MM HG
    • 174.00 °C. @ 760.00 mm Hg
    • 174 °C

    Flash point est.
    53.94 ˚C

    Flash point expt.

    • 133 °F (NTP, 1992)
    • 56 °C

    Solubility expt.

    • 0.1 to 1 mg/mL at 64 °F (NTP, 1992)
    • Insol in water and aq alkaline solns; miscible with benzene, petroleum ether, absolute alcohol, ether.
    • Soluble in ethanol.
    • Solubility in water: none

  • Synonyms

    • BENZOFURAN
    • 2,3-Benzofuran
    • 271-89-6
    • Coumarone
    • 1-Benzofuran
    • Benzo[b]furan
    • Cumarone
    • Benzofurfuran
    • Coumaron
    • Benzo(b)furan
    • 1-Oxindene
    • 1-Oxidene
    • Benzofuran (IUPAC)
    • NCI-C56166
    • CCRIS 2384
    • benzo[b]furane
    • HSDB 4173
    • NSC 1255
    • EINECS 205-982-6
    • BRN 0107704
    • DTXSID6020141
    • UNII-LK6946W774
    • CHEBI:35260
    • AI3-17613
    • BENZOFURAN [MI]
    • NSC-1255
    • BENZOFURAN [HSDB]
    • BENZOFURAN [IARC]
    • MFCD00005847
    • LK6946W774
    • Benzofuran (1mg/mL In Dichloromethane)
    • DTXCID20141
    • CHEMBL363614
    • 5-17-02-00003 (Beilstein Handbook Reference)
    • NCGC00091088-05
    • BENZOFURAN (IARC)
    • Cumaron
    • bezofuran
    • 1Oxindene
    • 1Oxidene
    • 1-Oxaindene
    • 2,3Benzofuran
    • 1-Benzofuran #
    • 2,3-Benzofuran, 99%
    • SCHEMBL5564
    • WLN: T56 BOJ
    • MLS002454357
    • CHEBI:36790
    • NSC1255
    • HMS2268K20
    • Tox21_400054
    • 2,3-Benzofuran, analytical standard
    • BDBM50167940
    • AKOS000121520
    • CCG-266071
    • DB04179
    • PS-5764
    • NCGC00091088-01
    • NCGC00091088-02
    • NCGC00091088-03
    • NCGC00091088-04
    • NCGC00091088-06
    • AT 33852
    • CAS-271-89-6
    • SMR000112279
    • Coumarone; 2,3-Benzofuran; Benzo[b]furan
    • DB-047175
    • B0060
    • NS00019800
    • EN300-16607
    • D88596
    • R 7204
    • A818947
    • Q410089
    • Z56347207
    • 205-982-6

  • Applications

    Benzofuran (CAS 271-89-6) is a bicyclic heteroaromatic scaffold used primarily as a versatile building block and intermediate in organic synthesis, enabling drug discovery and manufacture (the benzofuran core features in antiarrhythmics such as amiodarone and dronedarone; numerous benzofuran derivatives are explored for anti-inflammatory, anticancer, antimicrobial, and CNS activities), serving as a precursor to fragrance ingredients with warm/woody/balsamic notes, acting as a structural motif in agrochemicals (fungicidal and insecticidal derivatives), and functioning as a modular unit in materials science for fluorescent dyes, conjugated polymers, and donor–acceptor architectures in OLEDs, OFETs, and dye-sensitized solar cells due to tunable energy levels and emissive properties; in research it facilitates rapid library generation via site-selective functionalization (lithiation/metalation, halogenation) followed by cross-couplings (Suzuki, Sonogashira, Buchwald–Hartwig), and supports the synthesis of benzofuran-containing natural product analogs.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 396.55
    methanol 538.45
    isopropanol 256.94
    water 2.99
    ethyl acetate 230.73
    n-propanol 324.84
    acetone 209.73
    n-butanol 286.42
    acetonitrile 214.74
    DMF 274.02
    toluene 93.54
    isobutanol 241.49
    1,4-dioxane 448.35
    methyl acetate 185.78
    THF 633.23
    2-butanone 212.72
    n-pentanol 297.16
    sec-butanol 258.71
    n-hexane 73.07
    ethylene glycol 104.16
    NMP 179.41
    cyclohexane 49.4
    DMSO 335.91
    n-butyl acetate 105.47
    n-octanol 87.04
    chloroform 440.18
    n-propyl acetate 142.46
    acetic acid 243.2
    dichloromethane 530.17
    cyclohexanone 198.93
    propylene glycol 92.98
    isopropyl acetate 121.84
    DMAc 180.92
    2-ethoxyethanol 426.2
    isopentanol 234.41
    n-heptane 40.22
    ethyl formate 129.88
    1,2-dichloroethane 325.7
    n-hexanol 158.24
    2-methoxyethanol 450.47
    isobutyl acetate 104.36
    tetrachloromethane 77.02
    n-pentyl acetate 97.78
    transcutol 1385.82
    n-heptanol 77.72
    ethylbenzene 66.04
    MIBK 143.78
    2-propoxyethanol 276.5
    tert-butanol 229.81
    MTBE 209.69
    2-butoxyethanol 162.72
    propionic acid 171.69
    o-xylene 59.26
    formic acid 141.79
    diethyl ether 439.7
    m-xylene 60.81
    p-xylene 66.62
    chlorobenzene 106.95
    dimethyl carbonate 90.42
    n-octane 18.24
    formamide 258.49
    cyclopentanone 233.42
    2-pentanone 197.29
    anisole 191.26
    cyclopentyl methyl ether 260.01
    gamma-butyrolactone 270.61
    1-methoxy-2-propanol 299.2
    pyridine 284.38
    3-pentanone 158.27
    furfural 252.2
    n-dodecane 13.94
    diethylene glycol 213.93
    diisopropyl ether 112.16
    tert-amyl alcohol 214.21
    acetylacetone 176.25
    n-hexadecane 15.17
    acetophenone 129.69
    methyl propionate 169.13
    isopentyl acetate 106.35
    trichloroethylene 416.95
    n-nonanol 83.68
    cyclohexanol 161.6
    benzyl alcohol 136.79
    2-ethylhexanol 94.94
    isooctanol 73.05
    dipropyl ether 174.31
    1,2-dichlorobenzene 99.14
    ethyl lactate 74.88
    propylene carbonate 133.69
    n-methylformamide 232.14
    2-pentanol 214.71
    n-pentane 70.47
    1-propoxy-2-propanol 168.66
    1-methoxy-2-propyl acetate 136.83
    2-(2-methoxypropoxy) propanol 209.76
    mesitylene 42.66
    ε-caprolactone 192.26
    p-cymene 36.58
    epichlorohydrin 443.8
    1,1,1-trichloroethane 178.73
    2-aminoethanol 216.78
    morpholine-4-carbaldehyde 319.59
    sulfolane 267.8
    2,2,4-trimethylpentane 25.39
    2-methyltetrahydrofuran 416.67
    n-hexyl acetate 140.59
    isooctane 21.87
    2-(2-butoxyethoxy)ethanol 321.27
    sec-butyl acetate 107.79
    tert-butyl acetate 139.01
    decalin 29.0
    glycerin 128.47
    diglyme 528.42
    acrylic acid 144.21
    isopropyl myristate 76.17
    n-butyric acid 216.26
    acetyl acetate 102.01
    di(2-ethylhexyl) phthalate 57.83
    ethyl propionate 136.98
    nitromethane 309.64
    1,2-diethoxyethane 385.35
    benzonitrile 113.54
    trioctyl phosphate 42.06
    1-bromopropane 244.99
    gamma-valerolactone 306.92
    n-decanol 65.47
    triethyl phosphate 60.45
    4-methyl-2-pentanol 121.59
    propionitrile 210.62
    vinylene carbonate 131.2
    1,1,2-trichlorotrifluoroethane 196.81
    DMS 132.65
    cumene 53.97
    2-octanol 59.94
    2-hexanone 173.72
    octyl acetate 81.81
    limonene 53.18
    1,2-dimethoxyethane 462.8
    ethyl orthosilicate 62.17
    tributyl phosphate 57.01
    diacetone alcohol 161.23
    N,N-dimethylaniline 117.61
    acrylonitrile 207.17
    aniline 135.87
    1,3-propanediol 246.25
    bromobenzene 99.45
    dibromomethane 349.95
    1,1,2,2-tetrachloroethane 288.78
    2-methyl-cyclohexyl acetate 89.31
    tetrabutyl urea 72.19
    diisobutyl methanol 65.38
    2-phenylethanol 104.5
    styrene 85.39
    dioctyl adipate 97.98
    dimethyl sulfate 105.84
    ethyl butyrate 110.23
    methyl lactate 83.84
    butyl lactate 75.89
    diethyl carbonate 80.02
    propanediol butyl ether 139.82
    triethyl orthoformate 86.3
    p-tert-butyltoluene 35.3
    methyl 4-tert-butylbenzoate 107.36
    morpholine 491.18
    tert-butylamine 168.21
    n-dodecanol 53.82
    dimethoxymethane 347.1
    ethylene carbonate 112.29
    cyrene 133.69
    2-ethoxyethyl acetate 179.98
    2-ethylhexyl acetate 82.6
    1,2,4-trichlorobenzene 105.44
    4-methylpyridine 185.6
    dibutyl ether 161.28
    2,6-dimethyl-4-heptanol 65.38
    DEF 211.06
    dimethyl isosorbide 268.83
    tetrachloroethylene 217.91
    eugenol 133.88
    triacetin 150.09
    span 80 136.63
    1,4-butanediol 144.36
    1,1-dichloroethane 230.58
    2-methyl-1-pentanol 236.87
    methyl formate 140.5
    2-methyl-1-butanol 233.08
    n-decane 21.8
    butyronitrile 199.36
    3,7-dimethyl-1-octanol 97.0
    1-chlorooctane 64.44
    1-chlorotetradecane 31.5
    n-nonane 21.04
    undecane 16.77
    tert-butylcyclohexane 28.45
    cyclooctane 23.56
    cyclopentanol 192.01
    tetrahydropyran 403.85
    tert-amyl methyl ether 175.38
    2,5,8-trioxanonane 388.96
    1-hexene 173.54
    2-isopropoxyethanol 275.68
    2,2,2-trifluoroethanol 79.74
    methyl butyrate 157.15

    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
Orris butter 8002-73-1 Iris florentina L., fam. Iridaceae 0.01%
Michelia alba flower headspace (China) Michelia alba DC., fam. Magnoliaceae 0.14%
Hedyotis diffusa (Malaysia) Hedyotis diffusa Willd. (syn. Oldenlandia diffusa Roxb.), fam. Rubiaceae 1.3%
Cassia, bark (China) 5 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.34%