Bicyclo[3.1.0]hex-2-ene, 2-methyl-5-(1-methylethyl)-

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  • Identifiers

    CAS number
    2867-05-2

    Molecular formula
    C10H16

    SMILES
    CC1=CCC2(C1C2)C(C)C

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Woody 85.19%
    Herbal 64.19%
    Green 60.66%
    Spicy 58.77%
    Fresh 45.37%
    Terpenic 43.63%
    Citrus 41.44%
    Oily 39.29%
    Dry 38.74%
    Pine 38.35%

     

    Flavor
    Woody 77.21%
    Wood 64.16%
    Green 57.05%
    Herbal 49.53%
    Spice 48.58%
    Herb 47.32%
    Terpene 45.02%
    Citrus 41.16%
    Turpentine 37.58%
    Pine 35.89%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.8

    pKa est.
    9.93 (weak base)

    Molecular weight
    136.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point

    • 150.00 to 152.00 °C. @ 760.00 mm Hg

    Flash point

    • 36.52 ˚C est.

  • Synonyms

    • ALPHA-THUJENE
    • 2867-05-2
    • 3-Thujene
    • Bicyclo[3.1.0]hex-2-ene, 2-methyl-5-(1-methylethyl)-
    • THUJONE, (A + B)(SG)
    • 2-methyl-5-propan-2-ylbicyclo[3.1.0]hex-2-ene
    • Origanene
    • alpha-Thuiene
    • 2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hex-2-ene
    • alpha-Thujen
    • .alpha.-Thujene
    • Thujone,(a + b)(sg)
    • 2-Methyl-5-(1-methylethyl)-bicyclo(3.1.0)hex-2-ene
    • 2-methyl-5-(1-methylethyl)-bicyclo[3.1.0]hex-2-ene
    • CHEBI:50031
    • thujene (alpha-)
    • 4-methyl-1-propan-2-ylbicyclo[3.1.0]hex-3-ene
    • Thujene, .alpha.-
    • 5-Isopropyl-2-methylbicyclo[3.1.0]hex-2-ene
    • (-)-3-Thujene
    • (1R,5S)-thuj-2-ene
    • (1R)-(-)-thuj-3-ene
    • DTXSID20863038
    • DB-326055
    • NS00048720
    • EN300-7441739
    • 5-Isopropyl-2-methylbicyclo[3.1.0]hex-2-ene #
    • Q27121796

  • Applications

    Bicyclo[3.1.0]hex-2-ene, 2-methyl-5-(1-methylethyl)- (CAS 2867-05-2) is used as an organic synthesis intermediate and building block for assembling heterocyclic and polycyclic structures, supporting pharmaceutical and agrochemical research. Its strained alkene enables it to act as a dienophile in cycloaddition reactions, allowing rapid construction of complex ring systems. In materials science, it can serve as a specialty monomer or comonomer for polymers and high-performance resins. It is commonly evaluated in academic and industrial R&D settings to develop new synthetic methods and to explore reaction scope with strained bicyclic systems. As a scaffold, it supports medicinal and process chemistry research to access diverse bicyclic frameworks while respecting formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 422.14
    methanol 286.26
    isopropanol 483.87
    water 0.96
    ethyl acetate 685.27
    n-propanol 481.41
    acetone 696.17
    n-butanol 508.77
    acetonitrile 511.79
    DMF 516.94
    toluene 583.38
    isobutanol 385.94
    1,4-dioxane 1246.06
    methyl acetate 626.02
    THF 1428.35
    2-butanone 676.88
    n-pentanol 312.98
    sec-butanol 444.07
    n-hexane 218.24
    ethylene glycol 92.56
    NMP 288.66
    cyclohexane 264.0
    DMSO 326.08
    n-butyl acetate 624.59
    n-octanol 281.55
    chloroform 1140.17
    n-propyl acetate 361.37
    acetic acid 181.08
    dichloromethane 833.21
    cyclohexanone 610.71
    propylene glycol 155.0
    isopropyl acetate 580.5
    DMAc 474.58
    2-ethoxyethanol 417.99
    isopentanol 469.15
    n-heptane 197.37
    ethyl formate 285.13
    1,2-dichloroethane 618.64
    n-hexanol 620.65
    2-methoxyethanol 580.05
    isobutyl acetate 327.79
    tetrachloromethane 334.61
    n-pentyl acetate 348.95
    transcutol 1139.48
    n-heptanol 287.05
    ethylbenzene 329.06
    MIBK 523.57
    2-propoxyethanol 842.47
    tert-butanol 602.57
    MTBE 919.92
    2-butoxyethanol 430.82
    propionic acid 237.89
    o-xylene 352.42
    formic acid 49.95
    diethyl ether 930.24
    m-xylene 435.25
    p-xylene 420.61
    chlorobenzene 448.8
    dimethyl carbonate 247.56
    n-octane 94.7
    formamide 108.51
    cyclopentanone 707.51
    2-pentanone 603.28
    anisole 586.58
    cyclopentyl methyl ether 690.95
    gamma-butyrolactone 567.32
    1-methoxy-2-propanol 591.77
    pyridine 670.06
    3-pentanone 517.69
    furfural 441.12
    n-dodecane 73.2
    diethylene glycol 423.47
    diisopropyl ether 451.4
    tert-amyl alcohol 475.41
    acetylacetone 644.21
    n-hexadecane 84.19
    acetophenone 370.88
    methyl propionate 485.83
    isopentyl acetate 661.63
    trichloroethylene 830.23
    n-nonanol 265.43
    cyclohexanol 376.88
    benzyl alcohol 283.48
    2-ethylhexanol 374.54
    isooctanol 248.42
    dipropyl ether 665.84
    1,2-dichlorobenzene 396.38
    ethyl lactate 171.35
    propylene carbonate 332.97
    n-methylformamide 232.45
    2-pentanol 437.78
    n-pentane 220.42
    1-propoxy-2-propanol 642.91
    1-methoxy-2-propyl acetate 693.43
    2-(2-methoxypropoxy) propanol 418.63
    mesitylene 325.07
    ε-caprolactone 502.13
    p-cymene 276.39
    epichlorohydrin 790.23
    1,1,1-trichloroethane 747.71
    2-aminoethanol 190.44
    morpholine-4-carbaldehyde 523.59
    sulfolane 438.9
    2,2,4-trimethylpentane 115.91
    2-methyltetrahydrofuran 917.71
    n-hexyl acetate 498.14
    isooctane 128.97
    2-(2-butoxyethoxy)ethanol 540.35
    sec-butyl acetate 357.72
    tert-butyl acetate 648.5
    decalin 153.07
    glycerin 170.72
    diglyme 939.1
    acrylic acid 166.16
    isopropyl myristate 276.85
    n-butyric acid 367.05
    acetyl acetate 433.95
    di(2-ethylhexyl) phthalate 187.97
    ethyl propionate 392.81
    nitromethane 382.74
    1,2-diethoxyethane 749.6
    benzonitrile 356.92
    trioctyl phosphate 141.38
    1-bromopropane 585.25
    gamma-valerolactone 753.5
    n-decanol 211.49
    triethyl phosphate 218.33
    4-methyl-2-pentanol 330.11
    propionitrile 582.2
    vinylene carbonate 320.61
    1,1,2-trichlorotrifluoroethane 373.08
    DMS 403.48
    cumene 265.91
    2-octanol 213.97
    2-hexanone 433.57
    octyl acetate 293.06
    limonene 333.36
    1,2-dimethoxyethane 844.47
    ethyl orthosilicate 236.27
    tributyl phosphate 176.46
    diacetone alcohol 476.73
    N,N-dimethylaniline 361.1
    acrylonitrile 468.0
    aniline 422.82
    1,3-propanediol 307.87
    bromobenzene 522.73
    dibromomethane 636.11
    1,1,2,2-tetrachloroethane 740.81
    2-methyl-cyclohexyl acetate 351.1
    tetrabutyl urea 199.1
    diisobutyl methanol 301.25
    2-phenylethanol 427.09
    styrene 355.58
    dioctyl adipate 262.33
    dimethyl sulfate 239.06
    ethyl butyrate 454.7
    methyl lactate 221.36
    butyl lactate 221.38
    diethyl carbonate 301.0
    propanediol butyl ether 308.66
    triethyl orthoformate 358.96
    p-tert-butyltoluene 298.42
    methyl 4-tert-butylbenzoate 391.63
    morpholine 1039.65
    tert-butylamine 505.08
    n-dodecanol 174.07
    dimethoxymethane 673.19
    ethylene carbonate 322.34
    cyrene 228.77
    2-ethoxyethyl acetate 481.19
    2-ethylhexyl acetate 515.27
    1,2,4-trichlorobenzene 414.2
    4-methylpyridine 649.28
    dibutyl ether 468.86
    2,6-dimethyl-4-heptanol 301.25
    DEF 455.79
    dimethyl isosorbide 591.9
    tetrachloroethylene 488.12
    eugenol 324.73
    triacetin 372.5
    span 80 316.05
    1,4-butanediol 132.36
    1,1-dichloroethane 746.87
    2-methyl-1-pentanol 292.56
    methyl formate 189.97
    2-methyl-1-butanol 408.29
    n-decane 112.21
    butyronitrile 541.75
    3,7-dimethyl-1-octanol 330.73
    1-chlorooctane 270.72
    1-chlorotetradecane 139.03
    n-nonane 109.09
    undecane 87.58
    tert-butylcyclohexane 156.61
    cyclooctane 143.87
    cyclopentanol 360.27
    tetrahydropyran 1103.01
    tert-amyl methyl ether 569.6
    2,5,8-trioxanonane 608.87
    1-hexene 401.65
    2-isopropoxyethanol 364.26
    2,2,2-trifluoroethanol 102.17
    methyl butyrate 395.4

    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