Fluorocytosine supplier | CasNO.2022-85-7

Name
Fluorocytosine
EINECS 217-968-7
CAS No. 2022-85-7
Article Data31
CAS DataBase
Density 1.73 g/cm³
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
Appearance white crystalline solid
Safety 22-24/25-45-36/37-36/37/39-27-26
Risk Codes 40-36/37/38
Molecular Structure
Hazard Symbols Xn, T, Xi
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-;
PSA 71.77000
LogP 0.07240

Synthetic route

: 99429-06-8
2,5-difluoro-4-chloro-pyrimidine

: 2022-85-7
Flucytosine

Conditions

Conditions	Yield
With ammonia In hydrogenchloride; ethanol; water	98.1%

: 71-30-7
Cytosine

: 2022-85-7
Flucytosine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: C4H4FN3O

: 2022-85-7
Flucytosine

Conditions

Conditions	Yield
With ammonium hydroxide at 70 - 80℃; for 3h; Autoclave; Large scale;	52%

: 1310078-72-8
5-fluoro-2-(methylsulfanyl)pyrimidin-4-amine

: 2022-85-7
Flucytosine

Conditions

Conditions	Yield
With water; hydrogen bromide at 126℃; for 4h;	51%

: 701-87-1
2-ethylsulfanyl-5-fluoro-pyrimidin-4-ylamine

: 2022-85-7
Flucytosine

Conditions

Conditions	Yield
With hydrogen bromide
With hydrogen bromide

: 71-30-7
Cytosine

A: 2022-85-7
Flucytosine

B: 4-Difluoramino-cytosin

Conditions

Conditions	Yield
With fluorine In water at 0℃; for 1h;

: C7H8FN3O4

: 2022-85-7
Flucytosine

Conditions

Conditions	Yield
With ammonia In methanol at 50℃; for 5h;	26 g

: C8H10FN3O4

: 2022-85-7
Flucytosine

Conditions

Conditions	Yield
With ammonia In methanol at 50℃; for 5h; Solvent; Large scale;	2.67 kg

: 2022-85-7
Flucytosine

: 98-88-4
benzoyl chloride

: 10357-07-0
N-benzoyl-5-fluorocytosine

Conditions

Conditions	Yield
With pyridine at 0 - 20℃; for 16h; Inert atmosphere;	99%

: 2022-85-7
Flucytosine

: 202272-29-5
1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose

: 202272-32-0
(L)-5’-O-(t-butyldiphenylsilyl)-2’,3-dideoxy-2’-fluoro-5-fluorocytidine

Conditions

Conditions	Yield
Stage #1: Flucytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 1h; Stage #2: 1-O-acetyl-5-O-(t-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-(L)-erythron-pentofuranose With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 4h; Inert atmosphere;	99%

: 2022-85-7
Flucytosine

: 638-41-5
pentyl chloroformate

: 862508-03-0
(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamic acid amyl ester

Conditions

Conditions	Yield
With pyridine; tetrabutylammomium bromide In dichloromethane at 20℃; for 1.5h; Reagent/catalyst;	96%
With pyridine In dichloromethane at -10 - 20℃; for 2h; Concentration; Inert atmosphere;	94.3%
With pyridine	75%
With tetra(n-butyl)ammonium hydrogensulfate; triethylamine In chloroform; water at 5 - 10℃; for 1h;	300 g

: 2022-85-7
Flucytosine

: 107-13-1
acrylonitrile

: 3-(5-fluoro-1-cytosinyl)propionitrile

Conditions

Conditions	Yield
In ammonia for 1h;	95%
With triethylamine In water at 100℃; for 0.0833333h; Michael addition; microwave irradiation;	84%

: 2022-85-7
Flucytosine

: 55589-62-3
potassium acesulfame

: 5-fluorocytosine acesulfame potassium

Conditions

Conditions	Yield
In methanol at 45℃; Concentration; Temperature; Solvent;	95%

: 2022-85-7
Flucytosine

: 292638-85-8
acrylic acid methyl ester

: methyl 3-(5-fluoro-1-cytosinyl)propionate

Conditions

Conditions	Yield
In ammonia for 1h;	94%

: 2022-85-7
Flucytosine

: 14660-52-7
ethyl 5-bromovalerate

: 1379471-11-0
C11H16FN3O3

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;	93.3%

: 2022-85-7
Flucytosine

: 27821-07-4, 27930-18-3, 37076-71-4, 62211-93-2, 63903-44-6, 76497-54-6
1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose

: C22H28FN3O11

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 5 - 10℃; for 2h;	92.7%

: 2022-85-7
Flucytosine

: 14215-97-5
1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose

: 53294-73-8
1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5-fluorocytosine

Conditions

Conditions	Yield
Stage #1: Flucytosine With 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 3h; Heating; Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 8h;	91%

: 2022-85-7
Flucytosine

: 73-40-5
2-amino-1,9-dihydro-6H-purin-6-one

: copper(II) nitrate hydrate

: 7732-18-5
water

: 1310-73-2
sodium hydroxide

: [Cu2(5-fluorocytosine)(guanine)(OH)4(H2O)]*2H2O

Conditions

Conditions	Yield
In ethanol; water byproducts: NaNO3; hydrated metal nitrate refluxed for about 10 hs in a mixt. of EtOH and triethyl orthoformate; 5-fluorocytozine and guanine added separately (molar ratio 2:1:1); mixt. refluxed for several hs; vol. reduced; pH adjusted to 7 (aq. NaOH soln.) with stirring; ppt. filtered; washed (EtOH, Et2O); oven-dried at 50-60°C; elem. anal.;	91%

...Expand

: 2022-85-7
Flucytosine

: 147027-09-6
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate

: 764659-72-5
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

Conditions

Conditions	Yield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate With triethylsilane; iodine In dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: Flucytosine With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 0 - 20℃; for 1h; Reagent/catalyst; Inert atmosphere; stereoselective reaction;	91%
Stage #1: Flucytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane at 25 - 130℃; Inert atmosphere; Stage #2: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate With zirconium(IV) chloride In dichloromethane at 25 - 30℃; for 6h; Inert atmosphere;	80%

: 2022-85-7
Flucytosine

: acrylic acid ammonium salt

: 3-(5-fluoro-1-cytosinyl)propionic acid

Conditions

Conditions	Yield
In ammonia for 4h;	90%

: 2022-85-7
Flucytosine

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: N-(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)-3,4,5-trimethoxybenzamide

Conditions

Conditions	Yield
With pyridine at 100℃;	90%

: 75-77-4
chloro-trimethyl-silane

: 2022-85-7
Flucytosine

: =

Conditions

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane In toluene at 100℃;	90%

: 2022-85-7
Flucytosine

: 73-40-5
2-amino-1,9-dihydro-6H-purin-6-one

: zinc(II) nitrate hydrate

: 7732-18-5
water

: 1310-73-2
sodium hydroxide

: [Zn2(5-fluorocytosine)(guanine)(OH)4(H2O)]*2H2O

Conditions

Conditions	Yield
In ethanol; water byproducts: NaNO3; hydrated metal nitrate refluxed for about 10 hs in a mixt. of EtOH and triethyl orthoformate; 5-fluorocytozine and guanine added separately (molar ratio 2:1:1); mixt. refluxed for several hs; vol. reduced; pH adjusted to 7 (aq. NaOH soln.) with stirring; ppt. filtered; washed (EtOH, Et2O); oven-dried at 50-60°C; elem. anal.;	89%

...Expand

: 2022-85-7
Flucytosine

: 1215294-20-4
C10H6BrF6NO

: 1215294-34-0
C14H9F7N4O2

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	89%

: 2022-85-7
Flucytosine

: 27821-07-4, 27930-18-3, 37076-71-4, 62211-93-2, 63903-44-6, 76497-54-6
1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose

: 161599-46-8
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at 10 - 20℃; for 4h; Solvent;	88.6%
Stage #1: Flucytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 3h; Reflux; Stage #2: 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose With tin(IV) chloride In dichloromethane at -5℃; Inert atmosphere; Heating;	83.6%
Stage #1: Flucytosine With trifluorormethanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 2h; Reflux; Stage #2: 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose With trifluorormethanesulfonic acid at 20 - 55℃;	80%

: 2022-85-7
Flucytosine

: 1,2,3-tri-O-acetyl-α,β-D-ribofuranose-5-[phenylbis(isoamyl-L-aspartyl)]phosphate

: 2',3'-di-O-acetyl-5-fluorocytidine-5'-[phenylbis(isoamyl-L-aspartyl)]phosphate

Conditions

Conditions	Yield
Stage #1: Flucytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 4h; Vorbrueggen Nucleoside Synthesis; Reflux; Stage #2: 1,2,3-tri-O-acetyl-α,β-D-ribofuranose-5-[phenylbis(isoamyl-L-aspartyl)]phosphate With tin(IV) chloride In 1,2-dichloro-ethane at 20℃; for 3h; Reagent/catalyst; Solvent; Vorbrueggen Nucleoside Synthesis; diastereoselective reaction;	88%

: 2022-85-7
Flucytosine

: 2195-44-0
2-bromo-N-(4-fluorophenyl)acetamide

: 1215294-23-7
C12H10F2N4O2

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	87%

: 2022-85-7
Flucytosine

: 73-40-5
2-amino-1,9-dihydro-6H-purin-6-one

: nickel(II) nitrate hydrate

: 7732-18-5
water

: 1310-73-2
sodium hydroxide

: [Ni2(5-fluorocytosine)(guanine)(OH)4(H2O)]*2H2O

Conditions

Conditions	Yield
In ethanol; water byproducts: NaNO3; hydrated metal nitrate refluxed for about 10 hs in a mixt. of EtOH and triethyl orthoformate; 5-fluorocytozine and guanine added separately (molar ratio 2:1:1); mixt. refluxed for several hs; vol. reduced; pH adjusted to 7 (aq. NaOH soln.) with stirring; ppt. filtered; washed (EtOH, Et2O); oven-dried at 50-60°C; elem. anal.;	86%

...Expand

: 2-bromo-N-(4-chloro-3-(trifluoromethyl)phenyl)acetamide

: 2022-85-7
Flucytosine

: 1215294-09-9
C13H9ClF4N4O2

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	86%

: 2022-85-7
Flucytosine

: (4-acetoxy-1,3-dioxan-2-yl)methyl benzoate

: β-{4-[4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl]-1,3-dioxan-2-yl}methyl benzoate

Conditions

Conditions	Yield
Stage #1: Flucytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane at 120℃; for 12h; Inert atmosphere; Stage #2: (4-acetoxy-1,3-dioxan-2-yl)methyl benzoate With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 20℃; Inert atmosphere; stereoselective reaction;	86%

: 2022-85-7
Flucytosine

: 127204-71-1
2-phenylimidazo[2,1-b][1,3]benzothiazole-3-carbaldehyde

: C20H12FN5OS

Conditions

Conditions	Yield
With acetic acid In ethanol for 24h; Reflux;	85.1%

: 2022-85-7
Flucytosine

: 1215294-15-7
C8H6BrClFNO

: 1215294-31-7
C12H9ClF2N4O2

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	85%

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: Harmful Xn,Xi ; Toxic T
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.

Product Name

Fluorocytosine

Synthetic route

Fluorocytosine Chemical Properties

Fluorocytosine Uses

Fluorocytosine Toxicity Data With Reference

Fluorocytosine Safety Profile

Fluorocytosine Specification

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