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Fluorocytosine
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Name

Fluorocytosine

 EINECS 217-968-7
CAS No. 2022-85-7 Density 1.73 g/cm3
PSA 71.77000 LogP 0.07240
Solubility 1.5g/100mL (25 °C) in water Melting Point 298-300 °C (dec.)(lit.)
Formula C4H4FN3O Boiling Point 298oC
Molecular Weight 129.094 Flash Point 96.4°C
Transport Information N/A Appearance white crystalline solid
Safety 22-24/25-45-36/37-36/37/39-27-26 Risk Codes 40-36/37/38
Molecular Structure Molecular Structure of 2022-85-7 (Fluorocytosine) Hazard Symbols HarmfulXn, ToxicT, IrritantXi
Synonyms

5-Flurocytosine;4-amino-5-fluoro-3H-pyrimidin-2-one;Flucytosinum [INN-Latin];Ro 2-9915;Fluorcytosine;Flucytosin;Ancobon (TN);4-Amino-5-fluoro-2-pyrimidinol;Flucitosina [DCIT];5-Fluorocystosine;4-Amino-5-fluoro-2(1H)-pyrimidinone;Ancotyl;6-Amino-2-oxo-5-fluoropyrimidine;2-Hydroxy-4-amino-5-fluoropyrimidine;Flucytosine;Flucytosine (JP14/USP);5-FC;5FC;Alcobon;Cytosine, 5-fluoro- (6CI,7CI,8CI);5-Fluorocytosin;2(1H)-Pyrimidinone, 4-amino-5-fluoro- (8CI)(9CI);Ancotil;Ancobon;Cytosine, 5-fluoro-;

Article Data 31

Fluorocytosine Synthetic route

99429-06-8

2,5-difluoro-4-chloro-pyrimidine

2022-85-7

Flucytosine

Conditions
ConditionsYield
With ammonia In hydrogenchloride; ethanol; water98.1%
71-30-7

Cytosine

2022-85-7

Flucytosine

Conditions
ConditionsYield
Stage #1: Cytosine With hydrogen fluoride at -15 - 0℃; Inert atmosphere;
Stage #2: at -20℃; for 4h; Inert atmosphere; Further stages;		95.7%
With 1,1,1,3',3',3'-hexafluoro-propanol; fluorine at 20℃; under 1125.11 Torr; Temperature; Pressure; Reagent/catalyst; Inert atmosphere;87.4%
With formic acid for 1.5h; Time; Flow reactor; Autoclave;63%
With formic acid; fluorine at 9℃; for 0.0833333h; Temperature; Concentration; Inert atmosphere;
1993-63-1

4-amino-5-fluoro-2-methoxypyrimidine

2022-85-7

Flucytosine

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 40 - 60℃;95%
With hydrogenchloride In water at 100℃; for 4h;57%
945548-37-8

N-acetyl-5-bromocytosine

2022-85-7

Flucytosine

Conditions
ConditionsYield
Stage #1: N-acetyl-5-bromocytosine With acetamide; potassium fluoride In N,N-dimethyl-formamide at 130℃; for 5h; Inert atmosphere;
Stage #2: With ammonia In methanol at 40℃; for 12h; Reagent/catalyst; Solvent; Temperature;		93%

N-9-fluorenylmethoxycarbonyl-5-bromocytosine

2022-85-7

Flucytosine

Conditions
ConditionsYield
Stage #1: N-9-fluorenylmethoxycarbonyl-5-bromocytosine With potassium fluoride; tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 110℃; for 10h; Inert atmosphere;
Stage #2: With sodium hydroxide In 1,4-dioxane at 50℃; for 2h; Inert atmosphere;		91.1%

C7H12FNO2

57-13-6

urea

2022-85-7

Flucytosine

Conditions
ConditionsYield
Stage #1: C7H12FNO2; urea With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; for 1.5h; Large scale;
Stage #2: With hydrogenchloride In water at 0 - 25℃; for 2h; pH=6; pH-value; Temperature; Large scale;		84.2%

5-fluoropyrimidine-2,4-diamine

2022-85-7

Flucytosine

Conditions
ConditionsYield
With sulfuric acid; water; sodium nitrite at 1 - 20℃; for 1.7h;83%
With sulfuric acid; sodium nitrite In water at 0 - 40℃;82%
71-30-7

Cytosine

A

2022-85-7

Flucytosine

B

C4H5F2N3O2

Conditions
ConditionsYield
With formic acid for 1.5h; Time; Flow reactor; Sealed tube;A 66%
B n/a
With formic acid; fluorine for 1.5h; Flow reactor; Overall yield = 64 %;
1312324-60-9

5-fluoro-2-(methylsulfonyl)pyrimidin-4-amine

2022-85-7

Flucytosine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 3h;66%
134379-77-4

β-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine

A

98-00-0

(2-furyl)methyl alcohol

B

2022-85-7

Flucytosine

Conditions
ConditionsYield
With acetic acid at 35 - 40℃; for 1h; pH=3 - 4; Product distribution; Further Variations:; pH-values; Temperatures;A 58%
B n/a

Fluorocytosine Chemical Properties

Molecular structure of Fluorocytosine (CAS NO.2022-85-7) is:

Product Name: Fluorocytosine
CAS Registry Number: 2022-85-7
IUPAC Name: 6-amino-5-fluoro-1H-pyrimidin-2-one
Molecular Weight: 129.092463 [g/mol]
Molecular Formula: C4H4FN3O
XLogP3-AA: -0.9
H-Bond Donor: 2
H-Bond Acceptor: 3 
EINECS: 217-968-7
Melting Point: 298-300 °C (dec.)(lit.)
Surface Tension: 58.8 dyne/cm
Density: 1.73 g/cm3 
Storage temp.: 2-8 °C
Water Solubility: 1.5g/100mL (25 °C)
Sensitive: Light Sensitive 
Product Categories: PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines;Pyrimidine series;API;Phenylacetic acid;ketone;Nucleotides and Nucleosides;Antifungals for Research and Experimental Use;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Nucleotides

Fluorocytosine Uses

 Fluorocytosine (CAS NO.2022-85-7) is a synthetic antimycotic drug.

Fluorocytosine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD12 oral 500mg/kg (500mg/kg)   British UK Patent Application. Vol. #2067993,
mouse LD50 intraperitoneal 1190mg/kg (1190mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 566, 1963.
mouse LD50 intravenous 500mg/kg (500mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 566, 1963.
mouse LD50 subcutaneous 1gm/kg (1000mg/kg)   Chemotherapy Vol. 25, Pg. 54, 1979.
rat LD50 intraperitoneal 3811mg/kg (3811mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 10, Pg. 710, 1979.
rat LD50 intravenous > 600mg/kg (600mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 10, Pg. 710, 1979.
rat LD50 oral > 15gm/kg (15000mg/kg)   Drugs in Japan Vol. 6, Pg. 699, 1982.
rat LD50 subcutaneous 3336mg/kg (3336mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 935, 1979.
women TDLo oral 1080mg/kg/10D (1080mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA		 European Journal of Clinical Pharmacology. Vol. 51, 505.

Fluorocytosine Safety Profile

Hazard Codes: HarmfulXn,Xi ;ToxicT
Risk Statements: 40-36/37/38 
R40:Limited evidence of a carcinogenic effect. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-45-36/37-36/37/39-27-26 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37:Wear suitable protective clothing and gloves. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S27:Take off immediately all contaminated clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS: HA6040000
F: 10-23
Hazard Note: Toxic/Light Sensitive
HazardClass: IRRITANT, LIGHT SENSITIVE

Fluorocytosine Specification

 Fluorocytosine , its cas register number is 2022-85-7. It also can be called 2-Hydroxy-4-amino-5-fluoropyrimidine ; 4-Amino-5-fluoro-2(1H)-pyrimidinone ; 5-Fluorocytosine ; Alcobon ; Ancobon ; Ancotil .It is a white crystalline solid.

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