Tetrahydropyran-2-methanol

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  • Identifiers

    CAS number
    100-72-1

    Molecular formula
    C6H12O2

    SMILES
    C1CCOC(C1)CO

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 70.14%
    Ethereal 59.59%
    Fermented 58.18%
    Solvent 53.92%
    Sweet 51.03%
    Oily 50.78%
    Alcoholic 47.97%
    Caramellic 46.62%
    Musty 36.47%
    Winey 33.78%

     

    Flavor
    Caramel 47.15%
    Oily 42.23%
    Vegetable 38.48%
    Cauliflower 29.0%
    Warm 28.95%
    Roasted 25.44%
    Sweet 24.89%
    Faint 24.44%
    Musty 24.05%
    Alkaline 23.33%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.3

    pKa est.
    7.47 (neutral)

    Molecular weight
    116.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    197°C

    Flash point

    • 78.82 ˚C est.

  • Synonyms

    • TETRAHYDROPYRAN-2-METHANOL
    • 100-72-1
    • 2H-Pyran-2-methanol, tetrahydro-
    • 2-Hydroxymethyltetrahydropyran
    • Tetrahydropyran-2-carbinol
    • Pyran-2-methanol, tetrahydro-
    • 2-(Hydroxymethyl)tetrahydropyran
    • 2-Methanol tetrahydropyran
    • 2-Tetrahydropyranilcarbinol
    • Tetrahydropyran-2-ylmethanol
    • Tetrahydropyranyl-2-methanol
    • 2-Methyloltetrahydro-1,4-pyran
    • Tetrahydro-2H-pyran-2-methanol
    • NSC 5221
    • EINECS 202-882-4
    • JR71SUM5E9
    • BRN 0102998
    • AI3-14307
    • NSC-5221
    • 5-17-03-00136 (Beilstein Handbook Reference)
    • Tetrahydropyran2carbinol
    • 2Methanol tetrahydropyran
    • 2Tetrahydropyranilcarbinol
    • Tetrahydropyran2ylmethanol
    • Tetrahydropyranyl2methanol
    • RefChem:897193
    • Pyran2methanol, tetrahydro
    • 2Methyloltetrahydro1,4pyran
    • 2Hydroxymethyltetrahydropyran
    • 2HPyran2methanol, tetrahydro
    • 2-(HYDROXYMETHYL)TETRAHYDROPYRAN, (+-)-
    • (oxan-2-yl)methanol
    • oxan-2-ylmethanol
    • (Tetrahydro-2H-pyran-2-yl)methanol
    • Tetrahydro-2H-pyran-2-ylmethanol
    • MFCD00006624
    • 2-Methanol, tetrahydropyran
    • WLN: T6OTJ B1Q
    • NSC 5221; NSC 66493; Oxan-2-ylmethanol; Tetrahydro-2H-pyran-2-ylmethanol; Tetrahydropyran-2-carbinol; Tetrahydropyran-2-methanol
    • 2H-3,4,5,6-tetrahydropyran-2-ylmethan-1-ol
    • UNII-JR71SUM5E9
    • (Tetrahydro-2H-pyran-2-yl);methanol
    • 2-(Hydroxymethyl)tetrahydro-2H-pyran
    • 2-Hydromethyltetrahydropyran
    • tetrahydro-2-pyranylmethanol
    • SCHEMBL226684
    • SCHEMBL728160
    • 2-hydroxymethyl-tetrahydropyran
    • (tetrahydropyran-2-yl)methanol
    • tetrahydro-pyran-2-yl-methanol
    • orb1692036
    • SCHEMBL9532569
    • SCHEMBL12498842
    • SCHEMBL14603546
    • SCHEMBL15561310
    • SCHEMBL19748799
    • SCHEMBL27834870
    • SCHEMBL28897348
    • ROTONRWJLXYJBD-UHFFFAOYSA-
    • DTXSID40870441
    • NSC5221
    • CHEBI:228990
    • Tetrahydropyran-2-methanol, 98%
    • ALBB-020943
    • NSC66493
    • Tetrahydro-2-hydroxymethyl-2H-pyran
    • Tetrahydro-2H-pyran-2-ylmethanol #
    • NSC-66493
    • SBB008943
    • AKOS000120206
    • AKOS016843228
    • AB00784
    • EBC-618083
    • FT03071
    • SB22788
    • (TETRAHYDRO-PYRAN-2-YL)-METHANOL
    • AS-53912
    • SY003220
    • 3,4,5,6-tetrahydro-2H-pyran-2-methanol
    • HY-115051
    • CS-0034490
    • NS00015511
    • ST50949430
    • T0952
    • EN300-20690
    • P17277
    • 2-(HYDROXYMETHYL)TETRAHYDROPYRAN, (+/-)-
    • F067745
    • Q27281647
    • F0001-0026
    • Z104479808
    • InChI=1/C6H12O2/c7-5-6-3-1-2-4-8-6/h6-7H,1-5H2
    • 100-72-1

  • Applications

    Tetrahydropyran-2-methanol (CAS 100-72-1) is primarily used as an intermediate in organic synthesis, serving as a protected-hydroxymethyl building block for THP-protected derivatives in carbohydrate chemistry. It is commonly employed as a precursor in pharmaceutical synthesis to introduce THP-protected functionality and facilitate stepwise assembly of complex molecules. In polymer science, it can be used as a protected polyol building block that can be deprotected during processing, enabling controlled functionalization of polymer backbones. In industry, it provides a platform for specialized materials such as coatings, inks, and adhesives where selective hydroxyl reactivity is advantageous under appropriate regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1769.76
    methanol 2609.06
    isopropanol 1123.01
    water 33.26
    ethyl acetate 456.64
    n-propanol 1192.96
    acetone 638.27
    n-butanol 883.72
    acetonitrile 735.51
    DMF 857.48
    toluene 100.86
    isobutanol 694.49
    1,4-dioxane 1163.55
    methyl acetate 464.86
    THF 1049.09
    2-butanone 420.36
    n-pentanol 457.35
    sec-butanol 632.66
    n-hexane 18.98
    ethylene glycol 602.78
    NMP 572.58
    cyclohexane 45.06
    DMSO 1764.96
    n-butyl acetate 294.11
    n-octanol 137.28
    chloroform 1264.22
    n-propyl acetate 235.62
    acetic acid 1696.9
    dichloromethane 1059.02
    cyclohexanone 587.98
    propylene glycol 535.08
    isopropyl acetate 200.7
    DMAc 356.26
    2-ethoxyethanol 642.17
    isopentanol 507.86
    n-heptane 28.32
    ethyl formate 452.98
    1,2-dichloroethane 535.56
    n-hexanol 395.32
    2-methoxyethanol 1280.39
    isobutyl acetate 132.77
    tetrachloromethane 198.45
    n-pentyl acetate 150.44
    transcutol 1316.64
    n-heptanol 160.42
    ethylbenzene 41.1
    MIBK 169.4
    2-propoxyethanol 650.19
    tert-butanol 817.07
    MTBE 285.03
    2-butoxyethanol 328.12
    propionic acid 954.31
    o-xylene 73.89
    formic acid 966.84
    diethyl ether 362.26
    m-xylene 79.08
    p-xylene 59.41
    chlorobenzene 252.2
    dimethyl carbonate 93.89
    n-octane 10.72
    formamide 834.91
    cyclopentanone 669.66
    2-pentanone 318.68
    anisole 153.48
    cyclopentyl methyl ether 366.76
    gamma-butyrolactone 948.16
    1-methoxy-2-propanol 707.2
    pyridine 655.17
    3-pentanone 182.34
    furfural 852.38
    n-dodecane 9.52
    diethylene glycol 703.71
    diisopropyl ether 69.14
    tert-amyl alcohol 428.35
    acetylacetone 300.42
    n-hexadecane 10.33
    acetophenone 140.39
    methyl propionate 287.4
    isopentyl acetate 194.71
    trichloroethylene 941.56
    n-nonanol 113.32
    cyclohexanol 468.79
    benzyl alcohol 211.56
    2-ethylhexanol 165.14
    isooctanol 122.41
    dipropyl ether 180.41
    1,2-dichlorobenzene 199.5
    ethyl lactate 135.62
    propylene carbonate 424.89
    n-methylformamide 879.03
    2-pentanol 400.97
    n-pentane 30.41
    1-propoxy-2-propanol 423.94
    1-methoxy-2-propyl acetate 231.8
    2-(2-methoxypropoxy) propanol 223.58
    mesitylene 54.88
    ε-caprolactone 512.87
    p-cymene 50.11
    epichlorohydrin 820.98
    1,1,1-trichloroethane 422.79
    2-aminoethanol 952.01
    morpholine-4-carbaldehyde 706.05
    sulfolane 894.69
    2,2,4-trimethylpentane 17.07
    2-methyltetrahydrofuran 694.64
    n-hexyl acetate 184.09
    isooctane 16.13
    2-(2-butoxyethoxy)ethanol 367.4
    sec-butyl acetate 114.94
    tert-butyl acetate 174.75
    decalin 16.85
    glycerin 687.46
    diglyme 676.61
    acrylic acid 800.02
    isopropyl myristate 65.43
    n-butyric acid 1022.77
    acetyl acetate 245.49
    di(2-ethylhexyl) phthalate 78.05
    ethyl propionate 151.8
    nitromethane 1500.52
    1,2-diethoxyethane 322.07
    benzonitrile 297.86
    trioctyl phosphate 63.23
    1-bromopropane 295.21
    gamma-valerolactone 876.89
    n-decanol 81.48
    triethyl phosphate 75.7
    4-methyl-2-pentanol 159.23
    propionitrile 521.66
    vinylene carbonate 441.37
    1,1,2-trichlorotrifluoroethane 660.04
    DMS 126.53
    cumene 35.13
    2-octanol 93.15
    2-hexanone 194.31
    octyl acetate 88.05
    limonene 78.77
    1,2-dimethoxyethane 642.21
    ethyl orthosilicate 74.88
    tributyl phosphate 77.2
    diacetone alcohol 273.04
    N,N-dimethylaniline 86.52
    acrylonitrile 696.56
    aniline 320.03
    1,3-propanediol 1056.45
    bromobenzene 208.48
    dibromomethane 611.0
    1,1,2,2-tetrachloroethane 708.74
    2-methyl-cyclohexyl acetate 117.1
    tetrabutyl urea 89.53
    diisobutyl methanol 89.35
    2-phenylethanol 197.17
    styrene 64.43
    dioctyl adipate 103.38
    dimethyl sulfate 165.58
    ethyl butyrate 192.38
    methyl lactate 209.97
    butyl lactate 148.77
    diethyl carbonate 112.29
    propanediol butyl ether 301.88
    triethyl orthoformate 126.99
    p-tert-butyltoluene 49.39
    methyl 4-tert-butylbenzoate 140.29
    morpholine 1231.42
    tert-butylamine 415.56
    n-dodecanol 62.25
    dimethoxymethane 397.11
    ethylene carbonate 363.85
    cyrene 193.9
    2-ethoxyethyl acetate 210.57
    2-ethylhexyl acetate 136.58
    1,2,4-trichlorobenzene 242.11
    4-methylpyridine 442.86
    dibutyl ether 126.85
    2,6-dimethyl-4-heptanol 89.35
    DEF 353.35
    dimethyl isosorbide 302.94
    tetrachloroethylene 557.49
    eugenol 162.95
    triacetin 180.95
    span 80 219.91
    1,4-butanediol 393.12
    1,1-dichloroethane 562.34
    2-methyl-1-pentanol 259.58
    methyl formate 514.68
    2-methyl-1-butanol 450.93
    n-decane 16.11
    butyronitrile 531.06
    3,7-dimethyl-1-octanol 121.83
    1-chlorooctane 67.19
    1-chlorotetradecane 25.69
    n-nonane 15.26
    undecane 11.71
    tert-butylcyclohexane 17.69
    cyclooctane 14.54
    cyclopentanol 657.46
    tetrahydropyran 820.7
    tert-amyl methyl ether 161.59
    2,5,8-trioxanonane 424.19
    1-hexene 83.44
    2-isopropoxyethanol 342.21
    2,2,2-trifluoroethanol 479.33
    methyl butyrate 246.19

    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