2,2'-Dipyridyl disulfide

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  • Identifiers

    CAS number
    2127-03-9

    Molecular formula
    C10H8N2S2

    SMILES
    C1=CC=NC(=C1)SSC2=CC=CC=N2

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Meaty 65.41%
    Sulfurous 62.22%
    Roasted 59.55%
    Nutty 56.27%
    Earthy 47.93%
    Burnt 46.86%
    Coffee 46.57%
    Vegetable 42.5%
    Savory 38.84%
    Mushroom 38.4%

     

    Flavor
    Roasted 55.66%
    Meaty 44.66%
    Coffee 44.53%
    Sulfury 40.65%
    Nutty 36.13%
    Cooked 33.56%
    Vegetable 30.75%
    Onion 30.5%
    Bitter 27.87%
    Roast 26.93%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    3.02 (weak acid)

    Molecular weight
    220.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    385°C

    Flash point

    • 184.26 ˚C est.

    Solubility expt.

    • 25.5 [ug/mL] (The mean of the results at pH 7.4)

  • Synonyms

    • 2,2'-Dithiodipyridine
    • 2127-03-9
    • 2,2'-Dipyridyl disulfide
    • 2-(pyridin-2-yldisulfanyl)pyridine
    • 2,2'-Dipyridyldisulfide
    • 2-Dipyridyl disulfide
    • 2,2'-Dithiopyridine
    • Pyridine, 2,2'-dithiobis-
    • 2PDS
    • orthopyridyl disulfide
    • L6X912UPBU
    • DTXSID70175517
    • 2,2-dithiobispyridine
    • 2,2-PDS
    • RefChem:440289
    • DTXCID5098008
    • 218-343-1
    • 1,2-di(pyridin-2-yl)disulfane
    • Aldrithiol-2
    • Bis(2-pyridyl) disulfide
    • 2-Pyridinyl disulfide
    • Aldrithiol 2
    • 2-(2-pyridyldisulfanyl)pyridine
    • 2,2'-Dipyridinyl disulfide
    • 2,2'-disulfanediyldipyridine
    • MFCD00006287
    • 2,2'-pyridine disulfide
    • Bis(2-pyridinyl) disulfide
    • Bis(pyridin-2-yl) disulfide
    • 2-Pyridyl disulfide
    • OPSS
    • C10H8N2S2
    • 2,2-Dithiodipyridine"
    • Di-2-Pyridyl disulfide
    • bis(2-pyridyl)disulfide
    • 2,2'-Dithiobispyridine
    • 2,2'-dithiobis-pyridine
    • Di(2-Pyridyl) disulfide
    • 2,2'-Dithiobis(pyridine)
    • di(pyridin-2-yl) disulfide
    • Pyridine, 2,2'-dithiodi-
    • MLS001143364
    • 2-Pyridin-2-yldisulfanylpyridine
    • 2,2 inverted exclamation marka-Dipyridyl disulfide
    • NSC 94055
    • NSC-94055
    • NSC677438
    • NSC 677438
    • NSC-677438
    • SMR000473199
    • Pyridine, dithiobis-
    • dithiodipyridine
    • Di-2-pyridinyl disulfide; Di-2-pyridyl disulfide; NSC 677438; NSC 94055
    • 2,2'-Dipyridyldisulphide
    • 2,2'-dipyridyl disulphide
    • aldrithiol
    • pyridyldisulfide
    • pyridyl disulfide
    • dipyridyldisulfide
    • Aldrithol-2
    • AldrithiolTM-2
    • 2-pyridyldisulfide
    • dipyridyl disulfide
    • dipyridyl disulphide
    • 2-pyridyl-disulfide
    • Aldrithiol(TM)-2
    • di(2-pyridyl)disulfide
    • Pyridine,2'-dithiodi-
    • 2,2'-Diithiodipyridine
    • Pyridine,2'-dithiobis-
    • 2,2-dipyridyl disulfide
    • 2,2'-Bipyridyldisulfide
    • 2,2?-Dipyridyldisulfide
    • 2,2'-dipyridyl-disulfide
    • 2.2'-dipyridyl disulfide
    • di(pyridin-2-yl)disulfide
    • UNII-L6X912UPBU
    • 2-,2'-dipyridyl disulfide
    • NCIOpen2_006257
    • SCHEMBL21174
    • Aldrithiol(TM)-2, 98%
    • cid_65093
    • 2,2'-Disulphanediyldipyridine
    • 2,2'-Dithiodipyridine, powder
    • CHEMBL118678
    • orb1306880
    • SCHEMBL29349787
    • 1,2-Di(pyridin-2-yl)disulfide
    • BDBM60840
    • HAXFWIACAGNFHA-UHFFFAOYSA-
    • 1,2-bis(pyridin-2-yl)disulfane
    • 1,2-di(pyridine-2-yl)disulfane
    • 1,2-Bis(2-pyridinyl) disulfide
    • CHEBI:143170
    • 2-(2-Pyridinyldisulfanyl)pyridine
    • GLXC-10614
    • HMS2805F21
    • HY-Y1666
    • NSC94055
    • EINECS 218-343-1
    • 2-(2-Pyridinyldisulfanyl)pyridine #
    • BBL100074
    • SBB056659
    • STL220574
    • AKOS002248740
    • AC-4591
    • CS-W008788
    • EBC-605104
    • FD22537
    • 2-(2-(pyridin-2-yl)disulfanyl)pyridine
    • AS-13979
    • BP-20233
    • BP-23823
    • 2,2'-Dithiodipyridine, >=99.0% (GC)
    • DB-013948
    • DB-045524
    • D1114
    • NS00026825
    • ST45244395
    • EN300-172822
    • F136900
    • Q4596740
    • InChI=1/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H
    • 2127-03-9

  • Applications

    2,2'-Dipyridyl disulfide (CAS 2127-03-9) is commonly used in organic synthesis as a mild disulfide exchange reagent to convert thiols into disulfides and to install 2-pyridylthio (pyridyl disulfide) functionality on molecules; in bioconjugation, it enables thiol labeling and the preparation of SPDP-like linkers for protein and peptide modification; in polymer and materials science, it is employed to functionalize polymers with reversible disulfide cross-links for dynamic covalent bonding, self-healing coatings, and recyclable materials; in coatings, inks and adhesives, pyridyl disulfide-functionalized reagents facilitate surface grafting and crosslinking via disulfide exchange; and as a synthetic intermediate for coordination-chemistry ligands based on bis-pyridyl disulfide scaffolds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 16.05
    methanol 16.49
    isopropanol 8.26
    water 0.01
    ethyl acetate 149.33
    n-propanol 13.33
    acetone 217.99
    n-butanol 12.06
    acetonitrile 121.78
    DMF 487.64
    toluene 190.36
    isobutanol 9.93
    1,4-dioxane 283.3
    methyl acetate 160.08
    THF 554.79
    2-butanone 171.0
    n-pentanol 12.45
    sec-butanol 10.85
    n-hexane 2.17
    ethylene glycol 6.88
    NMP 582.69
    cyclohexane 11.78
    DMSO 469.84
    n-butyl acetate 98.1
    n-octanol 8.47
    chloroform 450.37
    n-propyl acetate 74.55
    acetic acid 62.72
    dichloromethane 621.78
    cyclohexanone 315.7
    propylene glycol 7.65
    isopropyl acetate 75.84
    DMAc 495.28
    2-ethoxyethanol 54.48
    isopentanol 13.58
    n-heptane 5.87
    ethyl formate 96.38
    1,2-dichloroethane 366.85
    n-hexanol 14.77
    2-methoxyethanol 91.1
    isobutyl acetate 46.39
    tetrachloromethane 29.74
    n-pentyl acetate 48.41
    transcutol 276.33
    n-heptanol 8.48
    ethylbenzene 49.04
    MIBK 57.58
    2-propoxyethanol 56.46
    tert-butanol 13.91
    MTBE 39.26
    2-butoxyethanol 31.74
    propionic acid 37.52
    o-xylene 71.78
    formic acid 20.93
    diethyl ether 60.11
    m-xylene 62.85
    p-xylene 57.54
    chlorobenzene 217.6
    dimethyl carbonate 99.04
    n-octane 1.9
    formamide 71.34
    cyclopentanone 503.42
    2-pentanone 109.36
    anisole 133.22
    cyclopentyl methyl ether 157.21
    gamma-butyrolactone 542.15
    1-methoxy-2-propanol 49.11
    pyridine 537.94
    3-pentanone 117.15
    furfural 609.91
    n-dodecane 2.0
    diethylene glycol 46.7
    diisopropyl ether 19.24
    tert-amyl alcohol 15.83
    acetylacetone 236.27
    n-hexadecane 2.46
    acetophenone 142.53
    methyl propionate 129.15
    isopentyl acetate 84.58
    trichloroethylene 890.41
    n-nonanol 9.48
    cyclohexanol 29.34
    benzyl alcohol 68.41
    2-ethylhexanol 19.8
    isooctanol 8.78
    dipropyl ether 52.28
    1,2-dichlorobenzene 195.57
    ethyl lactate 31.56
    propylene carbonate 228.97
    n-methylformamide 130.69
    2-pentanol 8.95
    n-pentane 2.22
    1-propoxy-2-propanol 46.82
    1-methoxy-2-propyl acetate 125.11
    2-(2-methoxypropoxy) propanol 58.18
    mesitylene 30.57
    ε-caprolactone 218.19
    p-cymene 34.95
    epichlorohydrin 633.5
    1,1,1-trichloroethane 205.99
    2-aminoethanol 11.79
    morpholine-4-carbaldehyde 461.01
    sulfolane 605.7
    2,2,4-trimethylpentane 2.48
    2-methyltetrahydrofuran 239.56
    n-hexyl acetate 51.25
    isooctane 1.5
    2-(2-butoxyethoxy)ethanol 73.34
    sec-butyl acetate 51.41
    tert-butyl acetate 80.74
    decalin 7.25
    glycerin 19.14
    diglyme 206.66
    acrylic acid 52.36
    isopropyl myristate 27.02
    n-butyric acid 52.9
    acetyl acetate 134.18
    di(2-ethylhexyl) phthalate 32.87
    ethyl propionate 74.51
    nitromethane 326.3
    1,2-diethoxyethane 127.68
    benzonitrile 163.05
    trioctyl phosphate 16.79
    1-bromopropane 96.0
    gamma-valerolactone 610.33
    n-decanol 8.24
    triethyl phosphate 47.74
    4-methyl-2-pentanol 7.42
    propionitrile 74.35
    vinylene carbonate 242.01
    1,1,2-trichlorotrifluoroethane 271.67
    DMS 108.12
    cumene 25.06
    2-octanol 6.04
    2-hexanone 70.74
    octyl acetate 32.07
    limonene 49.17
    1,2-dimethoxyethane 188.27
    ethyl orthosilicate 41.8
    tributyl phosphate 26.6
    diacetone alcohol 63.9
    N,N-dimethylaniline 75.43
    acrylonitrile 140.67
    aniline 117.33
    1,3-propanediol 17.89
    bromobenzene 284.18
    dibromomethane 308.61
    1,1,2,2-tetrachloroethane 473.62
    2-methyl-cyclohexyl acetate 70.66
    tetrabutyl urea 43.48
    diisobutyl methanol 14.97
    2-phenylethanol 64.47
    styrene 82.81
    dioctyl adipate 51.9
    dimethyl sulfate 198.03
    ethyl butyrate 91.98
    methyl lactate 50.1
    butyl lactate 33.79
    diethyl carbonate 68.48
    propanediol butyl ether 25.91
    triethyl orthoformate 64.9
    p-tert-butyltoluene 30.41
    methyl 4-tert-butylbenzoate 67.87
    morpholine 241.63
    tert-butylamine 8.79
    n-dodecanol 7.62
    dimethoxymethane 187.39
    ethylene carbonate 164.52
    cyrene 92.69
    2-ethoxyethyl acetate 112.03
    2-ethylhexyl acetate 74.8
    1,2,4-trichlorobenzene 241.23
    4-methylpyridine 364.3
    dibutyl ether 35.18
    2,6-dimethyl-4-heptanol 14.97
    DEF 179.8
    dimethyl isosorbide 187.83
    tetrachloroethylene 247.64
    eugenol 68.08
    triacetin 89.66
    span 80 41.88
    1,4-butanediol 8.36
    1,1-dichloroethane 185.54
    2-methyl-1-pentanol 15.61
    methyl formate 145.51
    2-methyl-1-butanol 13.04
    n-decane 2.74
    butyronitrile 62.38
    3,7-dimethyl-1-octanol 14.76
    1-chlorooctane 14.08
    1-chlorotetradecane 7.87
    n-nonane 2.28
    undecane 2.28
    tert-butylcyclohexane 4.58
    cyclooctane 4.22
    cyclopentanol 39.16
    tetrahydropyran 179.55
    tert-amyl methyl ether 41.61
    2,5,8-trioxanonane 139.45
    1-hexene 11.97
    2-isopropoxyethanol 35.84
    2,2,2-trifluoroethanol 31.32
    methyl butyrate 98.14

    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