Nitrofurantoin

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  • Identifiers

    CAS number
    67-20-9

    Molecular formula
    C8H6N4O5

    SMILES
    C1C(=O)NC(=O)N1/N=C/C2=CC=C(O2)[N+](=O)[O-]

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Odorless 59.98%
    Nutty 29.34%
    Sweet 27.32%
    Burnt 26.27%
    Caramellic 25.38%
    Roasted 24.75%
    Popcorn 24.68%
    Cooked 20.33%
    Savory 20.04%
    Buttery 17.83%

    Scent© AI

  • Properties

    XLogP3-AA
    -0.5

    Molecular weight
    238.16 g/mol

    Melting point expt.

    • 514 °F (decomposes) (NTP, 1992)
    • 223-228
    • 263 °C

    Flash point est.
    219.06 ˚C

    Solubility expt.

    • >35.7 [ug/mL] (The mean of the results at pH 7.4)
    • less than 0.1 mg/mL at 66 °F (NTP, 1992)
    • 79.5 mg/L (at 24 °C)
    • Soly (mg/100 ml): water (pH 7) 19.0; 95% ethanol 51.0; acetone 510; DMF 8000; peanut oil 2.1; glycerol 60; polyethylene glycol 1500.
    • Very slightly soluble in alcohol and practically insoluble in ether and water.
    • In water, 79 mg/l at 24 °C.

  • Synonyms

    • nitrofurantoin
    • 67-20-9
    • Macrodantin
    • Furadantin
    • 5-Nitrofurantoin
    • Nitrofurantoine
    • Furadantine
    • Furadantoin
    • Furadonine
    • Furadontin
    • Nifurantin
    • Furalan
    • Nitrofuradantin
    • Nitrofurantoina
    • Berkfurin
    • Chemiofuran
    • Furachel
    • Furadoine
    • Furadonin
    • Furantoin
    • Furatoin
    • Furobactina
    • Novofuran
    • Orafuran
    • Parfuran
    • Trantoin
    • Urantoin
    • Urofurin
    • Welfurin
    • Zoofurin
    • Cyantin
    • Cystit
    • Furina
    • Ituran
    • Nitoin
    • Urizept
    • Urodin
    • Urolong
    • Furadantine mc
    • Uro-Tablinen
    • Fur-ren
    • Benkfuran
    • Dantafur
    • Furadoninum
    • Furaloid
    • Macrobid
    • Macrofuran
    • Nierofu
    • Nitrex
    • Nitrofurantoinum
    • Fua Med
    • Cistofuran
    • Macrodantina
    • Macrofurin
    • N-Toin
    • Nifuretten
    • Alfuran
    • Berkfuran
    • Ceduran
    • Furabid
    • Furedan
    • Gerofuran
    • Phenurin
    • Siraliden
    • Uerineks
    • Urofuran
    • Urolisa
    • Macpac
    • PiyEloseptyl
    • Usaf ea-2
    • Furadantina MC
    • Furadantine-MC
    • Furophen T
    • Nitrofur-C
    • Ro-Antoin
    • Furadantin Retard
    • Uro-Selz
    • 1-(5-Nitro-2-furfurylideneamino)hydantoin
    • N-(5-Nitrofurfurylidene)-1-aminohydantoin
    • 1-((5-Nitrofurfurylidene)amino)hydantoin
    • 1-[(5-Nitrofurfurylidene)amino]hydantoin
    • N-(5-Nitro-2-furfurylidene)-1-aminohydantoin
    • 1-(5-Nitro-2-furfurylidenamino)hydantoin
    • NITROFURANTOIN, MACROCRYSTALLINE
    • Nitrofurantoin anhydrous
    • NCI-C55196
    • NSC 2107
    • Nitrofurantoine [INN-French]
    • Nitrofurantoinum [INN-Latin]
    • NSC 44150
    • CCRIS 1192
    • N-(5-Nitro-2-furfurylideno)-1-aminohydantoina
    • HSDB 3135
    • Nitrofurantoin macrocrystal
    • NSC-2107
    • 2,4-Imidazolidinedione, 1-[[(5-nitro-2-furanyl)methylene]amino]-
    • EINECS 200-646-5
    • Nitrofurantoin, macrocrystals
    • NITROFURANTOIN MACROCRYSTALLINE
    • UNII-927AH8112L
    • CHEBI:71415
    • AI3-26388
    • Hydantoin, 1-((5-nitrofurfurylidene)amino)-
    • Nitrofurantoinum anhydrous
    • MFCD00003224
    • NSC-44150
    • 1-(((5-Nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione
    • Nitrofurantoin Macrocrystals
    • 927AH8112L
    • DTXCID90972
    • MLS000028500
    • DTXSID7020972
    • 1-[[(5-Nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione
    • J01XE01
    • NSC2107
    • 2,4-Imidazolidinedione, 1-(((5-nitro-2-furanyl)methylene)amino)-
    • NSC44150
    • Nitrofurantoin [USP:INN:BAN:JAN]
    • MACROBID COMPONENT NITROFURANTOIN
    • furophen
    • urodil
    • NCGC00091505-01
    • NCGC00091505-07
    • SMR000058271
    • 1-((5-nitro-2-furanyl)methylene)amino-2,4-imidazolidenedione
    • uro-tablineu
    • 1-(((5-nitro-2-furanyl)methylene)amino)-2,4-imidazolidinedione
    • fua-med

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.27
    methanol 0.77
    isopropanol 0.19
    water 0.03
    ethyl acetate 0.61
    n-propanol 0.21
    acetone 3.5
    n-butanol 0.19
    acetonitrile 1.92
    DMF 47.21
    toluene 0.12
    isobutanol 0.16
    1,4-dioxane 2.06
    methyl acetate 2.66
    THF 3.96
    2-butanone 3.8
    n-pentanol 0.2
    sec-butanol 0.26
    n-hexane 0.01
    ethylene glycol 0.55
    NMP 55.57
    cyclohexane 0.01
    DMSO 116.61
    n-butyl acetate 0.97
    n-octanol 0.15
    chloroform 0.26
    n-propyl acetate 1.01
    acetic acid 1.08
    dichloromethane 0.66
    cyclohexanone 3.8
    propylene glycol 0.53
    isopropyl acetate 0.36
    DMAc 95.32
    2-ethoxyethanol 4.53
    isopentanol 0.25
    n-heptane 0.01
    ethyl formate 1.57
    1,2-dichloroethane 0.47
    n-hexanol 0.11
    2-methoxyethanol 7.91
    isobutyl acetate 0.41
    tetrachloromethane 0.02
    n-pentyl acetate 0.38
    transcutol 13.89
    n-heptanol 0.12
    ethylbenzene 0.12
    MIBK 0.66
    2-propoxyethanol 3.26
    tert-butanol 0.32
    MTBE 0.3
    2-butoxyethanol 1.66
    propionic acid 0.86
    o-xylene 0.17
    formic acid 2.69
    diethyl ether 0.17
    m-xylene 0.09
    p-xylene 0.26
    chlorobenzene 0.17
    dimethyl carbonate 1.91
    n-octane 0.0
    formamide 9.62
    cyclopentanone 6.58
    2-pentanone 1.08
    anisole 1.52
    cyclopentyl methyl ether 0.47
    gamma-butyrolactone 7.84
    1-methoxy-2-propanol 3.59
    pyridine 3.5
    3-pentanone 1.09
    furfural 15.29
    n-dodecane 0.01
    diethylene glycol 4.99
    diisopropyl ether 0.04
    tert-amyl alcohol 0.44
    acetylacetone 2.57
    n-hexadecane 0.01
    acetophenone 3.17
    methyl propionate 1.47
    isopentyl acetate 0.96
    trichloroethylene 1.19
    n-nonanol 0.17
    cyclohexanol 0.23
    benzyl alcohol 1.4
    2-ethylhexanol 0.14
    isooctanol 0.13
    dipropyl ether 0.28
    1,2-dichlorobenzene 0.28
    ethyl lactate 2.07
    propylene carbonate 2.71
    n-methylformamide 9.82
    2-pentanol 0.11
    n-pentane 0.0
    1-propoxy-2-propanol 2.12
    1-methoxy-2-propyl acetate 2.19
    2-(2-methoxypropoxy) propanol 6.68
    mesitylene 0.07
    ε-caprolactone 3.38
    p-cymene 0.15
    epichlorohydrin 6.16
    1,1,1-trichloroethane 0.16
    2-aminoethanol 0.68
    morpholine-4-carbaldehyde 31.6
    sulfolane 30.82
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 1.12
    n-hexyl acetate 0.54
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 4.84
    sec-butyl acetate 0.49
    tert-butyl acetate 0.52
    decalin 0.01
    glycerin 2.58
    diglyme 13.01
    acrylic acid 1.58
    isopropyl myristate 0.31
    n-butyric acid 0.61
    acetyl acetate 0.48
    di(2-ethylhexyl) phthalate 0.92
    ethyl propionate 1.06
    nitromethane 12.35
    1,2-diethoxyethane 1.37
    benzonitrile 1.79
    trioctyl phosphate 0.4
    1-bromopropane 0.12
    gamma-valerolactone 20.03
    n-decanol 0.14
    triethyl phosphate 1.39
    4-methyl-2-pentanol 0.09
    propionitrile 1.05
    vinylene carbonate 3.0
    1,1,2-trichlorotrifluoroethane 8.08
    DMS 1.88
    cumene 0.11
    2-octanol 0.09
    2-hexanone 1.64
    octyl acetate 0.42
    limonene 0.17
    1,2-dimethoxyethane 14.0
    ethyl orthosilicate 0.93
    tributyl phosphate 0.7
    diacetone alcohol 2.0
    N,N-dimethylaniline 1.31
    acrylonitrile 3.11
    aniline 0.54
    1,3-propanediol 0.94
    bromobenzene 0.14
    dibromomethane 0.23
    1,1,2,2-tetrachloroethane 0.83
    2-methyl-cyclohexyl acetate 1.23
    tetrabutyl urea 1.89
    diisobutyl methanol 0.12
    2-phenylethanol 0.82
    styrene 0.17
    dioctyl adipate 1.12
    dimethyl sulfate 8.64
    ethyl butyrate 1.17
    methyl lactate 3.43
    butyl lactate 1.07
    diethyl carbonate 1.16
    propanediol butyl ether 1.77
    triethyl orthoformate 1.24
    p-tert-butyltoluene 0.11
    methyl 4-tert-butylbenzoate 2.33
    morpholine 3.2
    tert-butylamine 0.1
    n-dodecanol 0.11
    dimethoxymethane 5.51
    ethylene carbonate 1.79
    cyrene 9.3
    2-ethoxyethyl acetate 1.15
    2-ethylhexyl acetate 0.75
    1,2,4-trichlorobenzene 0.64
    4-methylpyridine 2.91
    dibutyl ether 0.29
    2,6-dimethyl-4-heptanol 0.12
    DEF 4.74
    dimethyl isosorbide 10.47
    tetrachloroethylene 0.31
    eugenol 3.15
    triacetin 2.05
    span 80 1.98
    1,4-butanediol 0.53
    1,1-dichloroethane 0.17
    2-methyl-1-pentanol 0.29
    methyl formate 7.22
    2-methyl-1-butanol 0.26
    n-decane 0.01
    butyronitrile 0.67
    3,7-dimethyl-1-octanol 0.19
    1-chlorooctane 0.05
    1-chlorotetradecane 0.03
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.0
    cyclopentanol 0.33
    tetrahydropyran 0.46
    tert-amyl methyl ether 0.4
    2,5,8-trioxanonane 11.75
    1-hexene 0.03
    2-isopropoxyethanol 2.06
    2,2,2-trifluoroethanol 1.09
    methyl butyrate 2.2

    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