Trimethyl phosphonoacetate

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  • Identifiers

    CAS number
    5927-18-4

    Molecular formula
    C5H11O5P

    SMILES
    COC(=O)CP(=O)(OC)OC

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 57.93%
    Ethereal 47.25%
    Winey 37.47%
    Odorless 33.36%
    Green 32.31%
    Fresh 31.5%
    Apple 31.39%
    Sharp 27.98%
    Sour 26.18%
    Pungent 23.91%

     

    Flavor
    Fruity 67.23%
    Bitter 29.44%
    Green 28.04%
    Floral 25.3%
    Sharp 24.86%
    Tropical 24.77%
    Sweet 24.76%
    Fatty 23.86%
    Apple 23.2%
    Mild 21.6%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    -0.6

    pKa est.
    5.29 (weak acid)

    Molecular weight
    182.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    273°C

    Flash point

    • 97.25 ˚C est.

  • Synonyms

    • Trimethyl phosphonoacetate
    • 5927-18-4
    • methyl 2-dimethoxyphosphorylacetate
    • Trimethylacetyl phosphate
    • Acetic acid, (dimethoxyphosphinyl)-, methyl ester
    • DTXSID3064063
    • RefChem:899798
    • DTXCID5042588
    • 227-663-0
    • Methyl 2-(dimethoxyphosphoryl)acetate
    • Trimethyl phosphonacetate
    • MFCD00008452
    • Methyl (dimethoxyphosphoryl)acetate
    • Phosphonoacetic Acid Trimethyl Ester
    • Methyl Dimethylphosphonoacetate
    • Dimethylphosphonoacetic Acid Methyl Ester
    • (Carboxymethyl)phosphonic acid trimethyl ester
    • methyl-(dimethoxyphosphoryl)acetat
    • EINECS 227-663-0
    • NSC 84262
    • trimethyl phophonoacetate
    • SCHEMBL991
    • tri methyl phosphonoacetate
    • bmse000156
    • (dimethoxy-phosphoryl)-acetic acid methyl ester
    • EC 227-663-0
    • methyl-dimethylphosphonoacetate
    • methyl dimethylphosphono-acetate
    • methyl(dimethoxyphosphoryl)acetate
    • SIGOIUCRXKUEIG-UHFFFAOYSA-
    • Trimethyl phosphonoacetate, 98%
    • Methyl(dimethoxyphosphinyl)acetate
    • CHEBI:195100
    • BB_SC-05356
    • NSC84262
    • Methyl2-(dimethoxyphosphoryl)acetate
    • AC-812
    • BBL027713
    • methyl 2-(dimethyl phosphono)acetate
    • NSC-84262
    • STL373423
    • AKOS009157414
    • methyl 2-(dimethoxyphosphoryl)-acetate
    • AS-14883
    • SY002676
    • CS-0016054
    • NS00010004
    • P1265
    • EN300-33438
    • F11256
    • carbomethoxy-methane-phosphonic acid dimethyl ester
    • F215697
    • Acetic acid, 2-(dimethoxyphosphinyl)-, methyl ester
    • J-027517
    • Trimethyl phosphonoacetate, purum, >=98.0% (GC)
    • F8880-1395
    • InChI=1/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3
    • 5927-18-4

  • Applications

    Trimethyl phosphonoacetate (CAS 5927-18-4) is primarily used as an organic synthesis building block for phosphonate esters and phosphonate-containing motifs, enabling downstream transformations to diverse phosphorus-containing compounds. It is commonly used as a precursor in the development of pharmaceutical and agrochemical intermediates, as well as a scaffold for materials science applications such as coatings bearing phosphonate functionalities. In practical synthesis, it participates in reactions to generate vinyl phosphonates via Horner–Wadsworth–Emmons-type processes, supporting the design of functional monomers, polymers, and related materials. It also serves as a starting material for research into phosphonate-containing ligands and catalytic systems in coordination chemistry, and as a versatile reagent in R&D settings for exploring phosphonate motifs.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 346.0
    methanol 824.5
    isopropanol 237.03
    water 525.81
    ethyl acetate 87.01
    n-propanol 203.85
    acetone 169.32
    n-butanol 155.76
    acetonitrile 214.36
    DMF 740.53
    toluene 61.88
    isobutanol 126.35
    1,4-dioxane 455.42
    methyl acetate 148.36
    THF 363.92
    2-butanone 110.99
    n-pentanol 84.59
    sec-butanol 147.85
    n-hexane 7.49
    ethylene glycol 332.57
    NMP 479.75
    cyclohexane 32.72
    DMSO 546.1
    n-butyl acetate 24.95
    n-octanol 42.73
    chloroform 505.82
    n-propyl acetate 38.36
    acetic acid 252.8
    dichloromethane 470.55
    cyclohexanone 148.51
    propylene glycol 237.01
    isopropyl acetate 40.66
    DMAc 582.8
    2-ethoxyethanol 284.59
    isopentanol 88.42
    n-heptane 7.75
    ethyl formate 183.99
    1,2-dichloroethane 216.3
    n-hexanol 56.46
    2-methoxyethanol 766.27
    isobutyl acetate 22.45
    tetrachloromethane 94.44
    n-pentyl acetate 24.18
    transcutol 147.94
    n-heptanol 39.15
    ethylbenzene 25.63
    MIBK 36.22
    2-propoxyethanol 170.55
    tert-butanol 220.95
    MTBE 70.78
    2-butoxyethanol 89.37
    propionic acid 149.68
    o-xylene 51.73
    formic acid 621.92
    diethyl ether 93.43
    m-xylene 35.06
    p-xylene 37.5
    chlorobenzene 67.07
    dimethyl carbonate 87.22
    n-octane 3.81
    formamide 747.57
    cyclopentanone 181.31
    2-pentanone 66.55
    anisole 69.78
    cyclopentyl methyl ether 110.49
    gamma-butyrolactone 232.69
    1-methoxy-2-propanol 342.92
    pyridine 224.23
    3-pentanone 59.52
    furfural 336.91
    n-dodecane 3.67
    diethylene glycol 259.91
    diisopropyl ether 17.29
    tert-amyl alcohol 136.78
    acetylacetone 77.3
    n-hexadecane 4.18
    acetophenone 66.51
    methyl propionate 108.47
    isopentyl acetate 21.46
    trichloroethylene 291.09
    n-nonanol 38.05
    cyclohexanol 158.47
    benzyl alcohol 97.97
    2-ethylhexanol 26.81
    isooctanol 26.63
    dipropyl ether 29.0
    1,2-dichlorobenzene 67.09
    ethyl lactate 45.51
    propylene carbonate 111.42
    n-methylformamide 544.19
    2-pentanol 70.99
    n-pentane 13.36
    1-propoxy-2-propanol 78.6
    1-methoxy-2-propyl acetate 42.23
    2-(2-methoxypropoxy) propanol 62.97
    mesitylene 21.06
    ε-caprolactone 125.89
    p-cymene 15.74
    epichlorohydrin 311.32
    1,1,1-trichloroethane 134.26
    2-aminoethanol 353.03
    morpholine-4-carbaldehyde 502.46
    sulfolane 243.97
    2,2,4-trimethylpentane 5.31
    2-methyltetrahydrofuran 189.66
    n-hexyl acetate 33.13
    isooctane 2.63
    2-(2-butoxyethoxy)ethanol 84.24
    sec-butyl acetate 22.4
    tert-butyl acetate 36.41
    decalin 8.38
    glycerin 401.67
    diglyme 178.92
    acrylic acid 156.31
    isopropyl myristate 13.47
    n-butyric acid 126.03
    acetyl acetate 51.44
    di(2-ethylhexyl) phthalate 21.31
    ethyl propionate 41.41
    nitromethane 435.91
    1,2-diethoxyethane 43.18
    benzonitrile 91.34
    trioctyl phosphate 15.74
    1-bromopropane 97.76
    gamma-valerolactone 334.69
    n-decanol 27.1
    triethyl phosphate 23.5
    4-methyl-2-pentanol 31.85
    propionitrile 135.59
    vinylene carbonate 128.73
    1,1,2-trichlorotrifluoroethane 342.74
    DMS 33.5
    cumene 17.82
    2-octanol 25.78
    2-hexanone 38.93
    octyl acetate 20.11
    limonene 21.86
    1,2-dimethoxyethane 351.61
    ethyl orthosilicate 23.87
    tributyl phosphate 15.22
    diacetone alcohol 74.78
    N,N-dimethylaniline 64.59
    acrylonitrile 173.91
    aniline 132.44
    1,3-propanediol 366.5
    bromobenzene 56.5
    dibromomethane 268.43
    1,1,2,2-tetrachloroethane 310.5
    2-methyl-cyclohexyl acetate 29.05
    tetrabutyl urea 28.21
    diisobutyl methanol 16.54
    2-phenylethanol 59.56
    styrene 31.14
    dioctyl adipate 22.92
    dimethyl sulfate 139.62
    ethyl butyrate 26.63
    methyl lactate 117.1
    butyl lactate 32.31
    diethyl carbonate 23.78
    propanediol butyl ether 79.44
    triethyl orthoformate 27.6
    p-tert-butyltoluene 15.77
    methyl 4-tert-butylbenzoate 52.98
    morpholine 499.82
    tert-butylamine 119.34
    n-dodecanol 19.71
    dimethoxymethane 353.65
    ethylene carbonate 104.93
    cyrene 100.4
    2-ethoxyethyl acetate 37.54
    2-ethylhexyl acetate 17.94
    1,2,4-trichlorobenzene 83.54
    4-methylpyridine 198.28
    dibutyl ether 21.54
    2,6-dimethyl-4-heptanol 16.54
    DEF 162.63
    dimethyl isosorbide 90.8
    tetrachloroethylene 206.7
    eugenol 64.98
    triacetin 35.13
    span 80 50.13
    1,4-butanediol 142.17
    1,1-dichloroethane 172.11
    2-methyl-1-pentanol 55.28
    methyl formate 394.99
    2-methyl-1-butanol 90.06
    n-decane 6.0
    butyronitrile 123.22
    3,7-dimethyl-1-octanol 29.28
    1-chlorooctane 18.52
    1-chlorotetradecane 8.05
    n-nonane 5.4
    undecane 4.53
    tert-butylcyclohexane 6.24
    cyclooctane 9.56
    cyclopentanol 215.06
    tetrahydropyran 204.2
    tert-amyl methyl ether 59.87
    2,5,8-trioxanonane 118.03
    1-hexene 18.84
    2-isopropoxyethanol 119.37
    2,2,2-trifluoroethanol 222.55
    methyl butyrate 61.75

    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