3,4,5-Trimethoxybenzaldehyde

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  • Identifiers

    CAS number
    86-81-7

    Molecular formula
    C10H12O4

    SMILES
    COC1=CC(=CC(=C1OC)OC)C=O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Floral 72.6%
    Sweet 71.62%
    Vanilla 67.63%
    Spicy 55.59%
    Woody 51.63%
    Powdery 47.34%
    Green 43.09%
    Balsamic 41.91%
    Creamy 38.07%
    Phenolic 36.73%

    Scent© AI

  • Properties

    XLogP3-AA
    0.9

    Molecular weight
    196.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    309°C

    Flash point est.
    122.37 ˚C

  • Synonyms

    • 3,4,5-TRIMETHOXYBENZALDEHYDE
    • 86-81-7
    • Benzaldehyde, 3,4,5-trimethoxy-
    • MFCD00003364
    • EINECS 201-701-6
    • NSC 16692
    • BRN 0395163
    • 3,4,5-trimethoxy-benzaldehyde
    • WL86YD76N6
    • BENZALDEHYDE,3,4,5-TRIMETHOXY-
    • AI3-36673
    • NSC-16692
    • 3,4,5-trimethoxy benzaldehyde
    • DTXSID4058948
    • 4-08-00-02719 (Beilstein Handbook Reference)
    • UNII-WL86YD76N6
    • NSC16692
    • Trimethoprim Intermediates
    • 3,5-Trimethoxybenzaldehyde
    • SCHEMBL96635
    • 3,4,5 trimethoxybenzaldehyde
    • 3,4,5 -trimethoxybenzaldehyde
    • 3,4,5,-trimethoxybenzaldehyde
    • Benzaldehyde, 3,4,5trimethoxy
    • CHEMBL3577781
    • DTXCID9048514
    • 3, 4, 5-trimethoxybenzaldehyde
    • 3,4,5,-trimethoxy benzaldehyde
    • 3, 4, 5-trimethoxy-benzaldehyde
    • BCP30525
    • STR03224
    • AC7996
    • BBL007764
    • NSC778227
    • STK498479
    • 3,4,5-Trimethoxybenzaldehyde, 98%
    • BENZALDEHYDE,3,4,5TRIMETHOXY
    • AKOS000118928
    • CCG-231504
    • CS-W010602
    • FT28524
    • HY-W009886
    • NSC-778227
    • AC-11732
    • PD002060
    • SY010811
    • DB-056953
    • 3,4,5-Trimethoxy-benzaldehyde;NSC 16692
    • NS00039152
    • T0059
    • EN300-19082
    • 3,4,5-Trimethoxy-benzaldehyde; NSC 16692;
    • A841837
    • Q15634093
    • F3099-6595
    • Z104472688
    • 201-701-6

  • Applications

    3,4,5-Trimethoxybenzaldehyde (TMBA) is an electron-rich aromatic intermediate broadly utilized in organic synthesis and applied research: it serves as a versatile building block for 3,4,5-trimethoxy-stilbenes and -cinnamates via Wittig/Knoevenagel chemistry in drug discovery (e.g., microtubule-inhibitor scaffolds and 3,4,5-trimethoxy resveratrol analogs with anticancer/anti-inflammatory potential), for Schiff-base anil intermediates and azomethine polymers in liquid-crystal, nonlinear-optical, and organic-electronics materials, for assembling 3,4,5-trimethoxybenzyl/phenylacetic derivatives in pharma and agrochemical libraries, and as a “protected” form that can be demethylated to 3,4,5-trihydroxybenzaldehyde used in antioxidants, metal–organic framework (MOF) ligands, and functional polymers; in addition, its activated aldehyde group engages readily in reductive amination, aldol, Henry, and condensation reactions, enabling efficient diversification of electron-rich aryl frameworks from lab scale to manufacturing.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 90.62
    methanol 143.09
    isopropanol 57.68
    water 2.42
    ethyl acetate 420.62
    n-propanol 60.73
    acetone 667.23
    n-butanol 45.64
    acetonitrile 716.12
    DMF 855.52
    toluene 60.29
    isobutanol 41.47
    1,4-dioxane 628.46
    methyl acetate 615.93
    THF 600.98
    2-butanone 345.32
    n-pentanol 44.16
    sec-butanol 48.88
    n-hexane 5.36
    ethylene glycol 163.3
    NMP 587.11
    cyclohexane 23.92
    DMSO 1086.85
    n-butyl acetate 203.27
    n-octanol 43.57
    chloroform 838.19
    n-propyl acetate 248.99
    acetic acid 447.3
    dichloromethane 1435.53
    cyclohexanone 485.48
    propylene glycol 52.31
    isopropyl acetate 162.66
    DMAc 500.7
    2-ethoxyethanol 252.87
    isopentanol 40.27
    n-heptane 10.63
    ethyl formate 549.2
    1,2-dichloroethane 899.73
    n-hexanol 56.0
    2-methoxyethanol 438.81
    isobutyl acetate 102.52
    tetrachloromethane 169.41
    n-pentyl acetate 110.9
    transcutol 229.59
    n-heptanol 38.44
    ethylbenzene 52.93
    MIBK 92.71
    2-propoxyethanol 184.46
    tert-butanol 84.05
    MTBE 79.44
    2-butoxyethanol 108.1
    propionic acid 240.05
    o-xylene 63.71
    formic acid 264.07
    diethyl ether 126.63
    m-xylene 49.42
    p-xylene 84.85
    chlorobenzene 232.19
    dimethyl carbonate 305.54
    n-octane 6.56
    formamide 615.85
    cyclopentanone 703.17
    2-pentanone 203.41
    anisole 167.92
    cyclopentyl methyl ether 180.37
    gamma-butyrolactone 1229.85
    1-methoxy-2-propanol 185.36
    pyridine 453.88
    3-pentanone 197.31
    furfural 1057.86
    n-dodecane 6.17
    diethylene glycol 250.1
    diisopropyl ether 31.32
    tert-amyl alcohol 63.22
    acetylacetone 421.91
    n-hexadecane 7.32
    acetophenone 232.65
    methyl propionate 372.04
    isopentyl acetate 139.59
    trichloroethylene 1529.85
    n-nonanol 39.22
    cyclohexanol 87.05
    benzyl alcohol 143.73
    2-ethylhexanol 50.4
    isooctanol 33.5
    dipropyl ether 70.9
    1,2-dichlorobenzene 285.98
    ethyl lactate 137.95
    propylene carbonate 585.94
    n-methylformamide 692.74
    2-pentanol 31.56
    n-pentane 5.19
    1-propoxy-2-propanol 108.21
    1-methoxy-2-propyl acetate 190.31
    2-(2-methoxypropoxy) propanol 90.65
    mesitylene 39.07
    ε-caprolactone 436.51
    p-cymene 49.37
    epichlorohydrin 1053.76
    1,1,1-trichloroethane 542.49
    2-aminoethanol 98.3
    morpholine-4-carbaldehyde 647.8
    sulfolane 1122.27
    2,2,4-trimethylpentane 4.91
    2-methyltetrahydrofuran 323.36
    n-hexyl acetate 126.08
    isooctane 3.57
    2-(2-butoxyethoxy)ethanol 109.89
    sec-butyl acetate 104.52
    tert-butyl acetate 141.44
    decalin 14.54
    glycerin 148.53
    diglyme 359.93
    acrylic acid 322.37
    isopropyl myristate 46.84
    n-butyric acid 230.09
    acetyl acetate 345.77
    di(2-ethylhexyl) phthalate 53.34
    ethyl propionate 202.16
    nitromethane 1659.47
    1,2-diethoxyethane 128.95
    benzonitrile 270.93
    trioctyl phosphate 44.54
    1-bromopropane 158.46
    gamma-valerolactone 841.11
    n-decanol 30.62
    triethyl phosphate 106.32
    4-methyl-2-pentanol 20.96
    propionitrile 274.14
    vinylene carbonate 631.72
    1,1,2-trichlorotrifluoroethane 690.38
    DMS 214.16
    cumene 41.32
    2-octanol 29.16
    2-hexanone 155.8
    octyl acetate 66.4
    limonene 63.42
    1,2-dimethoxyethane 538.44
    ethyl orthosilicate 80.56
    tributyl phosphate 59.09
    diacetone alcohol 149.52
    N,N-dimethylaniline 101.18
    acrylonitrile 535.31
    aniline 122.36
    1,3-propanediol 133.5
    bromobenzene 246.2
    dibromomethane 666.42
    1,1,2,2-tetrachloroethane 936.53
    2-methyl-cyclohexyl acetate 115.03
    tetrabutyl urea 76.9
    diisobutyl methanol 31.92
    2-phenylethanol 123.43
    styrene 71.49
    dioctyl adipate 89.53
    dimethyl sulfate 525.91
    ethyl butyrate 172.34
    methyl lactate 192.73
    butyl lactate 78.18
    diethyl carbonate 161.37
    propanediol butyl ether 77.59
    triethyl orthoformate 108.3
    p-tert-butyltoluene 43.95
    methyl 4-tert-butylbenzoate 136.68
    morpholine 465.49
    tert-butylamine 40.94
    n-dodecanol 24.15
    dimethoxymethane 470.93
    ethylene carbonate 504.42
    cyrene 166.29
    2-ethoxyethyl acetate 168.52
    2-ethylhexyl acetate 112.88
    1,2,4-trichlorobenzene 318.58
    4-methylpyridine 313.22
    dibutyl ether 55.09
    2,6-dimethyl-4-heptanol 31.92
    DEF 313.51
    dimethyl isosorbide 225.67
    tetrachloroethylene 714.87
    eugenol 125.04
    triacetin 172.98
    span 80 68.4
    1,4-butanediol 71.03
    1,1-dichloroethane 459.17
    2-methyl-1-pentanol 38.93
    methyl formate 939.23
    2-methyl-1-butanol 37.27
    n-decane 9.49
    butyronitrile 200.4
    3,7-dimethyl-1-octanol 37.65
    1-chlorooctane 41.1
    1-chlorotetradecane 18.31
    n-nonane 8.99
    undecane 7.51
    tert-butylcyclohexane 10.25
    cyclooctane 8.72
    cyclopentanol 137.33
    tetrahydropyran 270.8
    tert-amyl methyl ether 62.73
    2,5,8-trioxanonane 190.74
    1-hexene 20.77
    2-isopropoxyethanol 132.56
    2,2,2-trifluoroethanol 312.42
    methyl butyrate 309.45

    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
Cymbopogon microstachys Cymbopogon microstachys (Hook. f.) S. Soenarko, fam. Poaceae (Gramineae) 1.0%
Cyperus scariosus Cyperus scariosus R.Br., fam. Cupressaceae 1.86%