Flucytosine

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  • Identifiers

    CAS number
    2022-85-7

    Molecular formula
    C4H4FN3O

    SMILES
    C1=NC(=O)NC(=C1F)N

    Safety labels

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 74.34%
    Bitter 23.99%
    Burnt 23.14%
    Cooked 18.41%
    Roasted 17.99%
    Savory 17.27%
    Meaty 17.15%
    Animal 16.08%
    Nutty 14.43%
    Musty 14.28%

     

    Flavor
    Bitter 78.69%
    Odorless 43.07%
    Mild 27.66%
    Bread crust 20.92%
    Nitrile 20.51%
    Scallion 19.98%
    Very strong 19.94%
    Formyl 19.86%
    Roasted peanuts 19.86%
    Taco 19.77%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.9

    pKa est.
    6.91 (neutral)

    Molecular weight
    129.09 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    327°C

    Melting point expt.

    • 296 °C
    • 295-297 °C (dec)

    Flash point

    • 193.41 ˚C est.

    Solubility expt.

    • >19.4 [ug/mL] (The mean of the results at pH 7.4)
    • 15000 mg/L (at 25 °C)
    • In water, 1.5 g/100 mL at 25 °C
    • Slightly soluble in alcohol; practically insoluble in chloroform, ether
    • 1 g in about 12 mL 0.1 N HCL
    • 1.92e+00 g/L

  • Synonyms

    • 5-Fluorocytosine
    • flucytosine
    • 2022-85-7
    • Fluorocytosine
    • Ancobon
    • Ancotil
    • 5-Fluorocystosine
    • Flucytosin
    • Fluocytosine
    • 5-Fluorocytosin
    • Fluorcytosine
    • 5-FC
    • Alcobon
    • Flucytosinum
    • 117969-88-7
    • 4-amino-5-fluoropyrimidin-2-ol
    • 5-fluoro cytosine
    • Flucitosina
    • Cytosine, 5-fluoro-
    • Ro 2-9915
    • 4-Amino-5-fluoropyrimidin-2(1H)-one
    • 4-Amino-5-fluoro-2(1H)-pyrimidinone
    • 5-Flurocytosine
    • 5-Flucytosine
    • 2(1H)-Pyrimidinone, 4-amino-5-fluoro-
    • 2-Hydroxy-4-amino-5-fluoropyrimidine
    • Ro 29915 E/265601
    • 2-Pyrimidinol, 4-amino-5-fluoro- (9CI)
    • 6-amino-5-fluoro-1H-pyrimidin-2-one
    • Flucytosinum [INN-Latin]
    • Ancobon (TN)
    • 130256-61-0
    • Flucytosine (Ancobon)
    • flucytosina
    • 4-Amino-5-fluoro-2-hydroxypyrimidine
    • CHEBI:5100
    • NSC 103805
    • Ro-2-9915
    • HSDB 3082
    • 2(1H)-Pyrimidinone, 6-amino-5-fluoro-
    • 2-Pyrimidinol, 4-amino-5-fluoro-
    • EINECS 217-968-7
    • MFCD00006035
    • Ro-29915
    • NSC-103805
    • DTXSID3023059
    • UNII-D83282DT06
    • 2(1H)-Pyrimidinone, 4-amino-5-fluoro-)
    • NSC103805
    • D83282DT06
    • MLS000069463
    • DTXCID403059
    • 2(1H)-Pyrimidinone, 5-fluoro-3,4-dihydro-4-imino- (9CI)
    • 4-amino-5-fluoro-1,2-dihydropyrimidin-2-one
    • 5-FLUORO-4-IMINO-1,2,3,4-TETRAHYDROPYRIMIDIN-2-ONE
    • EC 217-968-7
    • Flucytosine [USAN)
    • 4-Amino-5-fluoro-1H-pyrimidin-2-one
    • Flucytosine [USAN:USP:INN:BAN:JAN]
    • NCGC00016599-01
    • Flucitosina [DCIT]
    • SMR000059047
    • CAS-2022-85-7
    • 4-AMINO-5-FLUORO-2(1H)-PYRIMIDINE
    • 6-amino-5-fluoro-1,2-dihydropyrimidin-2-one
    • FLUCYTOSINE [USAN]
    • Flucytosinum (INN-Latin)
    • FLUCYTOSINE (MART.)
    • FLUCYTOSINE [MART.]
    • FLUCYTOSINE (USP-RS)
    • FLUCYTOSINE [USP-RS]
    • Flucytosone
    • Ancotyl
    • FLUCYTOSINE (EP MONOGRAPH)
    • FLUCYTOSINE (USP IMPURITY)
    • FLUCYTOSINE [EP MONOGRAPH]
    • FLUCYTOSINE [USP IMPURITY]
    • FLUCYTOSINE (USP MONOGRAPH)
    • FLUCYTOSINE [USP MONOGRAPH]
    • Flucytosine (USAN:USP:INN:BAN:JAN)
    • pyrimidine, 4-amino-5-fluoro-2-hydroxy-
    • 6-Amino-2-oxo-5-fluoropyrimidine
    • 6-Amino-5-fluoro-2(1H)-pyrimidinone
    • Flourocytosine
    • Ancoban
    • 4-AMINO-2-HYDROXY-5-FLUOROPYRIMIDINE
    • 5-fluorocytocine
    • 5-fluoro-cytosine
    • 4-Amino-5-fluoro-2-hyroxypyrimidine
    • Flucytosinum (Latin)
    • 6-amino-5-fluoropyrimidin-2(1H)-one
    • GL663142 & 5FC
    • Flucytosine (Standard)
    • CPD000059047
    • ST028644
    • 6-amino-5-fluoro-3-hydropyrimidin-2-one
    • Opera_ID_178
    • 5-fluorocytosine Form I
    • FLUCYTOSINE [MI]
    • Prestwick0_000934
    • Prestwick1_000934
    • Prestwick2_000934
    • Prestwick3_000934
    • FLUCYTOSINE [INN]
    • FLUCYTOSINE [JAN]
    • 5-fluorocytosine Form II
    • F0321
    • FLUCYTOSINE [HSDB]
    • 5-Fluorocytosine (5-FC)
    • Flucytosine 100 microg/mL in Acetonitrile:Water
    • WLN: T6MVNJ DZ EF
    • CHEMBL1463
    • SCHEMBL24063
    • BSPBio_000868
    • FLUCYTOSINE [WHO-DD]
    • FLUCYTOSINE [WHO-IP]
    • MLS000759519
    • MLS001076503
    • MLS001424013
    • Flucytosine, 5-Fluorocytosine
    • SPBio_003037
    • EMTRICITABINE IMPURITY E
    • BPBio1_000956
    • GL663142 & 4-Amino-5-fluoropyrimidin-2(1H)-one
    • Flucytosine (JP18/USP/INN)
    • SCHEMBL14696800
    • HY-B0139R
    • D01AE21

  • Applications

    Flucytosine (CAS 2022-85-7) is used in pharmaceutical development as an active pharmaceutical ingredient (API) and a chemical intermediate in antifungal drug programs, often evaluated in dosage forms and in combination strategies; in biotechnology and research, it serves as a selective agent in microbiology and yeast genetics due to its conversion to toxic metabolites, enabling selection in culture systems; in medicinal chemistry, it functions as a nucleoside analog building block for the synthesis of other nucleoside-based compounds; in analytical and quality-control contexts, it may be used as a reference standard for method development and validation; all uses are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.01
    methanol 1.86
    isopropanol 0.57
    water 2.55
    ethyl acetate 0.04
    n-propanol 0.72
    acetone 0.31
    n-butanol 0.6
    acetonitrile 0.14
    DMF 3.53
    toluene 0.03
    isobutanol 0.36
    1,4-dioxane 0.14
    methyl acetate 0.11
    THF 0.52
    2-butanone 0.27
    n-pentanol 0.36
    sec-butanol 0.44
    n-hexane 0.03
    ethylene glycol 0.91
    NMP 6.2
    cyclohexane 0.01
    DMSO 15.44
    n-butyl acetate 0.16
    n-octanol 0.1
    chloroform 0.02
    n-propyl acetate 0.07
    acetic acid 0.56
    dichloromethane 0.06
    cyclohexanone 0.34
    propylene glycol 0.71
    isopropyl acetate 0.05
    DMAc 5.98
    2-ethoxyethanol 1.28
    isopentanol 0.47
    n-heptane 0.05
    ethyl formate 0.22
    1,2-dichloroethane 0.05
    n-hexanol 0.25
    2-methoxyethanol 2.44
    isobutyl acetate 0.03
    tetrachloromethane 0.02
    n-pentyl acetate 0.14
    transcutol 1.53
    n-heptanol 0.23
    ethylbenzene 0.03
    MIBK 0.14
    2-propoxyethanol 1.02
    tert-butanol 0.53
    MTBE 0.12
    2-butoxyethanol 1.01
    propionic acid 0.31
    o-xylene 0.05
    formic acid 1.59
    diethyl ether 0.11
    m-xylene 0.03
    p-xylene 0.04
    chlorobenzene 0.01
    dimethyl carbonate 0.1
    n-octane 0.01
    formamide 2.82
    cyclopentanone 0.47
    2-pentanone 0.18
    anisole 0.07
    cyclopentyl methyl ether 0.15
    gamma-butyrolactone 0.46
    1-methoxy-2-propanol 1.22
    pyridine 0.21
    3-pentanone 0.13
    furfural 1.04
    n-dodecane 0.01
    diethylene glycol 1.44
    diisopropyl ether 0.04
    tert-amyl alcohol 0.48
    acetylacetone 0.15
    n-hexadecane 0.01
    acetophenone 0.14
    methyl propionate 0.09
    isopentyl acetate 0.17
    trichloroethylene 0.04
    n-nonanol 0.11
    cyclohexanol 0.2
    benzyl alcohol 0.16
    2-ethylhexanol 0.16
    isooctanol 0.18
    dipropyl ether 0.2
    1,2-dichlorobenzene 0.02
    ethyl lactate 0.24
    propylene carbonate 0.21
    n-methylformamide 1.54
    2-pentanol 0.23
    n-pentane 0.03
    1-propoxy-2-propanol 0.72
    1-methoxy-2-propyl acetate 0.22
    2-(2-methoxypropoxy) propanol 1.16
    mesitylene 0.03
    ε-caprolactone 0.29
    p-cymene 0.07
    epichlorohydrin 0.28
    1,1,1-trichloroethane 0.02
    2-aminoethanol 1.47
    morpholine-4-carbaldehyde 2.13
    sulfolane 2.44
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.22
    n-hexyl acetate 0.12
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 1.12
    sec-butyl acetate 0.04
    tert-butyl acetate 0.09
    decalin 0.01
    glycerin 1.5
    diglyme 2.06
    acrylic acid 0.37
    isopropyl myristate 0.06
    n-butyric acid 0.28
    acetyl acetate 0.03
    di(2-ethylhexyl) phthalate 0.2
    ethyl propionate 0.06
    nitromethane 0.73
    1,2-diethoxyethane 0.22
    benzonitrile 0.09
    trioctyl phosphate 0.14
    1-bromopropane 0.05
    gamma-valerolactone 1.1
    n-decanol 0.09
    triethyl phosphate 0.2
    4-methyl-2-pentanol 0.15
    propionitrile 0.15
    vinylene carbonate 0.17
    1,1,2-trichlorotrifluoroethane 0.72
    DMS 0.08
    cumene 0.03
    2-octanol 0.11
    2-hexanone 0.17
    octyl acetate 0.09
    limonene 0.08
    1,2-dimethoxyethane 1.55
    ethyl orthosilicate 0.19
    tributyl phosphate 0.15
    diacetone alcohol 0.48
    N,N-dimethylaniline 0.18
    acrylonitrile 0.22
    aniline 0.1
    1,3-propanediol 1.39
    bromobenzene 0.01
    dibromomethane 0.04
    1,1,2,2-tetrachloroethane 0.05
    2-methyl-cyclohexyl acetate 0.17
    tetrabutyl urea 0.39
    diisobutyl methanol 0.14
    2-phenylethanol 0.17
    styrene 0.02
    dioctyl adipate 0.13
    dimethyl sulfate 0.44
    ethyl butyrate 0.17
    methyl lactate 0.43
    butyl lactate 0.41
    diethyl carbonate 0.13
    propanediol butyl ether 0.81
    triethyl orthoformate 0.22
    p-tert-butyltoluene 0.06
    methyl 4-tert-butylbenzoate 0.45
    morpholine 0.38
    tert-butylamine 0.24
    n-dodecanol 0.06
    dimethoxymethane 0.79
    ethylene carbonate 0.11
    cyrene 1.24
    2-ethoxyethyl acetate 0.19
    2-ethylhexyl acetate 0.12
    1,2,4-trichlorobenzene 0.03
    4-methylpyridine 0.19
    dibutyl ether 0.09
    2,6-dimethyl-4-heptanol 0.14
    DEF 0.57
    dimethyl isosorbide 1.28
    tetrachloroethylene 0.05
    eugenol 0.69
    triacetin 0.18
    span 80 0.6
    1,4-butanediol 0.63
    1,1-dichloroethane 0.02
    2-methyl-1-pentanol 0.29
    methyl formate 0.65
    2-methyl-1-butanol 0.44
    n-decane 0.01
    butyronitrile 0.19
    3,7-dimethyl-1-octanol 0.11
    1-chlorooctane 0.02
    1-chlorotetradecane 0.01
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.01
    cyclopentanol 0.3
    tetrahydropyran 0.1
    tert-amyl methyl ether 0.16
    2,5,8-trioxanonane 1.77
    1-hexene 0.07
    2-isopropoxyethanol 0.5
    2,2,2-trifluoroethanol 0.46
    methyl butyrate 0.15

    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