1,2,4-Trimethoxybenzene

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  • Identifiers

    CAS number
    135-77-3

    Molecular formula
    C9H12O3

    SMILES
    COC1=CC(=C(C=C1)OC)OC

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 2096.0

  • Odor profile

    Sweet 63.27%
    Vanilla 61.76%
    Phenolic 61.49%
    Spicy 55.32%
    Earthy 52.01%
    Nutty 45.96%
    Smoky 45.73%
    Anisic 40.5%
    Woody 38.04%
    Powdery 35.07%

    Scent© AI

  • Properties

    XLogP3-AA
    2.1

    Molecular weight
    168.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    258°C

    Flash point est.
    94.5 ˚C

  • Synonyms

    • 1,2,4-Trimethoxybenzene
    • 135-77-3
    • Benzene, 1,2,4-trimethoxy-
    • Hydroxyhydroquinone trimethyl ether
    • UNII-3KU3WD07SS
    • EINECS 205-219-7
    • 3KU3WD07SS
    • EPA Pesticide Chemical Code 040515
    • DTXSID5035163
    • AI3-20797
    • MFCD00008360
    • CHEMBL1668605
    • DTXCID3015163
    • AGIQIOSHSMJYJP-UHFFFAOYSA-
    • 1,2,5-TRIMETHOXYBENZENE
    • 1,3,4-TRIMETHOXYBENZENE
    • TRIMETHOXYBENZENE, 1,2,4-
    • 1,2,4-BENZENETRIOL TRIMETHYL ETHER
    • 2,4,5-trimethoxybenzene
    • 1,3,4-trimethoxy benzene
    • SCHEMBL481491
    • 1,2,4-Trimethoxybenzene, 97%
    • CHEBI:167092
    • STR04198
    • Tox21_300993
    • BDBM50336489
    • AKOS015851701
    • CS-W017803
    • FT33474
    • PS-5199
    • NCGC00164023-01
    • NCGC00164023-02
    • NCGC00254895-01
    • AC-23662
    • CAS-135-77-3
    • SY014691
    • DB-038069
    • NS00024400
    • T1130
    • EN300-187594
    • F11207
    • Q27257439
    • Z1255382978
    • 205-219-7

  • Applications

    1,2,4-Trimethoxybenzene (CAS 135-77-3) is an electron-rich, thermally and oxidatively stable aromatic ether widely used as a versatile building block in fine organic synthesis; it serves as an intermediate toward pharmaceuticals and agrochemicals, a precursor to dyes, pigments, and functional polymers, and a scaffold that tunes solubility and electronic properties in materials. Its three methoxy groups strongly direct reactivity, enabling efficient electrophilic substitutions, formylation, halogenation, selective demethylation, and modern cross-couplings, providing access to diverse benzaldehyde, benzoic, and heterocyclic derivatives; it is also employed as a model substrate in mechanistic studies (EAS, redox, C–H activation) and in catalyst/photocatalyst evaluation. In materials science, 1,2,4-trimethoxybenzene underpins hole-transport components, weak donor–acceptor systems, and chromophore scaffolds, and appears in fragrance/flavor R&D, benefiting from good stability and solvent compatibility for applications from lab-scale to pilot production.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 130.58
    methanol 152.33
    isopropanol 100.16
    water 3.52
    ethyl acetate 403.5
    n-propanol 111.93
    acetone 403.94
    n-butanol 92.75
    acetonitrile 451.87
    DMF 437.68
    toluene 119.12
    isobutanol 83.09
    1,4-dioxane 834.9
    methyl acetate 427.77
    THF 663.73
    2-butanone 259.56
    n-pentanol 71.71
    sec-butanol 92.24
    n-hexane 24.43
    ethylene glycol 153.34
    NMP 364.88
    cyclohexane 108.31
    DMSO 567.59
    n-butyl acetate 170.27
    n-octanol 53.32
    chloroform 1316.15
    n-propyl acetate 204.33
    acetic acid 441.94
    dichloromethane 1380.77
    cyclohexanone 425.32
    propylene glycol 76.36
    isopropyl acetate 176.91
    DMAc 344.63
    2-ethoxyethanol 267.06
    isopentanol 78.35
    n-heptane 34.1
    ethyl formate 336.64
    1,2-dichloroethane 789.88
    n-hexanol 87.03
    2-methoxyethanol 438.58
    isobutyl acetate 109.14
    tetrachloromethane 343.84
    n-pentyl acetate 99.92
    transcutol 282.21
    n-heptanol 51.53
    ethylbenzene 94.89
    MIBK 101.57
    2-propoxyethanol 208.67
    tert-butanol 208.24
    MTBE 182.32
    2-butoxyethanol 110.83
    propionic acid 243.65
    o-xylene 118.71
    formic acid 172.91
    diethyl ether 243.26
    m-xylene 89.18
    p-xylene 126.65
    chlorobenzene 256.21
    dimethyl carbonate 199.83
    n-octane 17.04
    formamide 321.67
    cyclopentanone 475.42
    2-pentanone 181.57
    anisole 203.77
    cyclopentyl methyl ether 245.64
    gamma-butyrolactone 751.39
    1-methoxy-2-propanol 210.61
    pyridine 441.11
    3-pentanone 197.98
    furfural 652.91
    n-dodecane 13.6
    diethylene glycol 232.47
    diisopropyl ether 68.54
    tert-amyl alcohol 141.25
    acetylacetone 306.51
    n-hexadecane 15.89
    acetophenone 191.93
    methyl propionate 283.71
    isopentyl acetate 138.61
    trichloroethylene 1320.25
    n-nonanol 51.15
    cyclohexanol 181.01
    benzyl alcohol 150.32
    2-ethylhexanol 72.54
    isooctanol 46.05
    dipropyl ether 128.69
    1,2-dichlorobenzene 286.43
    ethyl lactate 111.56
    propylene carbonate 403.16
    n-methylformamide 312.02
    2-pentanol 65.78
    n-pentane 25.01
    1-propoxy-2-propanol 119.6
    1-methoxy-2-propyl acetate 162.28
    2-(2-methoxypropoxy) propanol 103.06
    mesitylene 72.4
    ε-caprolactone 378.42
    p-cymene 65.82
    epichlorohydrin 763.33
    1,1,1-trichloroethane 824.09
    2-aminoethanol 126.05
    morpholine-4-carbaldehyde 499.79
    sulfolane 676.72
    2,2,4-trimethylpentane 20.01
    2-methyltetrahydrofuran 409.38
    n-hexyl acetate 125.8
    isooctane 13.12
    2-(2-butoxyethoxy)ethanol 125.33
    sec-butyl acetate 118.43
    tert-butyl acetate 181.68
    decalin 44.05
    glycerin 165.76
    diglyme 346.35
    acrylic acid 275.55
    isopropyl myristate 62.76
    n-butyric acid 243.99
    acetyl acetate 347.53
    di(2-ethylhexyl) phthalate 57.01
    ethyl propionate 204.7
    nitromethane 885.62
    1,2-diethoxyethane 160.37
    benzonitrile 222.42
    trioctyl phosphate 43.57
    1-bromopropane 264.35
    gamma-valerolactone 611.58
    n-decanol 41.15
    triethyl phosphate 120.4
    4-methyl-2-pentanol 42.56
    propionitrile 251.78
    vinylene carbonate 432.92
    1,1,2-trichlorotrifluoroethane 591.2
    DMS 171.5
    cumene 68.25
    2-octanol 38.15
    2-hexanone 135.88
    octyl acetate 75.23
    limonene 93.08
    1,2-dimethoxyethane 501.23
    ethyl orthosilicate 107.13
    tributyl phosphate 56.7
    diacetone alcohol 161.61
    N,N-dimethylaniline 133.35
    acrylonitrile 365.76
    aniline 181.59
    1,3-propanediol 180.01
    bromobenzene 288.43
    dibromomethane 766.8
    1,1,2,2-tetrachloroethane 936.31
    2-methyl-cyclohexyl acetate 128.21
    tetrabutyl urea 71.11
    diisobutyl methanol 52.92
    2-phenylethanol 121.81
    styrene 119.42
    dioctyl adipate 98.98
    dimethyl sulfate 306.35
    ethyl butyrate 176.89
    methyl lactate 142.04
    butyl lactate 69.05
    diethyl carbonate 163.5
    propanediol butyl ether 72.25
    triethyl orthoformate 128.72
    p-tert-butyltoluene 65.74
    methyl 4-tert-butylbenzoate 137.49
    morpholine 650.45
    tert-butylamine 121.32
    n-dodecanol 35.36
    dimethoxymethane 370.93
    ethylene carbonate 374.69
    cyrene 164.99
    2-ethoxyethyl acetate 147.05
    2-ethylhexyl acetate 121.24
    1,2,4-trichlorobenzene 329.92
    4-methylpyridine 309.85
    dibutyl ether 88.61
    2,6-dimethyl-4-heptanol 52.92
    DEF 257.38
    dimethyl isosorbide 235.79
    tetrachloroethylene 735.28
    eugenol 119.5
    triacetin 156.95
    span 80 85.04
    1,4-butanediol 72.67
    1,1-dichloroethane 622.88
    2-methyl-1-pentanol 65.84
    methyl formate 368.11
    2-methyl-1-butanol 75.78
    n-decane 21.41
    butyronitrile 199.39
    3,7-dimethyl-1-octanol 53.51
    1-chlorooctane 67.01
    1-chlorotetradecane 33.22
    n-nonane 21.65
    undecane 16.34
    tert-butylcyclohexane 32.14
    cyclooctane 36.81
    cyclopentanol 216.98
    tetrahydropyran 460.06
    tert-amyl methyl ether 135.74
    2,5,8-trioxanonane 219.76
    1-hexene 60.89
    2-isopropoxyethanol 158.68
    2,2,2-trifluoroethanol 277.78
    methyl butyrate 250.67

    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
Lilac headspace Syringa vulgaris L., fam. Oleaceae 0.5%
Hyacinth, living flower headspace 1a Hyacinthus orientalis L., fam. Liliaceae 5.0%
Hyacinth, picked flower headspace 1b Hyacinthus orientalis L., fam. Liliaceae 1.19%
Cymbidium goeringii flower headspace Cymbidium goeringii (Rchb.f.) Rchb.f., fam Orchidaceae 0.05%
Phalaenopsis veichiana headspace Phalaenopsis veitchiana, fam. Orchidaceae 2.3%
Mullilam leaf (India) Zanthoxylum rhetsa D.C. syn. Z. limonella (Dennst.) Alston, fam. Rutaceae 0.01%