Product Name

  • Name

    5-Fluorouracil

  • EINECS 200-085-6
  • CAS No. 51-21-8
  • Article Data130
  • CAS DataBase
  • Density 1.53 g/cm3
  • Solubility insoluble in water
  • Hazard Symbols HarmfulXn,ToxicT,CorrosiveC,IrritantXi
  • Synonyms Ro-2-9757;Phtoruracil;2,4(1H,3H)-Pyrimidinedione,5-fluoro-;Phthoruracil;5-Fluoro-2,4(1H, 3H)-pyrimidinedione;Fluoroplex;5-Fluoracyl;Efudex;Effluderm (free base);U 8953;Adrucil;Efurix;5-Ftouracyl;U-8953;Arumel;Kecimeton;Fluro Uracil;Uracil, 5-fluoro- (VAN 8CI);Fluracil;Efudix;Ro 2-9757;Fluracilum;5-FU;5-Fluoro-2,4-pyrimidinedione;
  • PSA 65.72000
  • LogP -0.79770

Synthetic route

trans-5-fluoro-6-acetoxy-5,6-dihydrouracil
56311-36-5, 100814-55-9, 100814-58-2

trans-5-fluoro-6-acetoxy-5,6-dihydrouracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With triethylamine at 60℃;100%
(+/-)-t-6-butoxy-r-5-ethoxycarbonyl-5-fluoro-5,6-dihydrouracil
65906-75-4, 76481-58-8, 81033-59-2, 84471-52-3, 84471-53-4

(+/-)-t-6-butoxy-r-5-ethoxycarbonyl-5-fluoro-5,6-dihydrouracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With hydrogenchloride for 1h; Product distribution; Heating; variation of reagent, temperature; in ethanol;95%
methyl 5-fluoro-4-methoxy-2,6-dioxohexahydro-5-pyrimidinecarboxylate
65905-96-6

methyl 5-fluoro-4-methoxy-2,6-dioxohexahydro-5-pyrimidinecarboxylate

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With hydrogenchloride In water for 2.5h;95%
2,5-difluoro-4-chloro-pyrimidine
99429-06-8

2,5-difluoro-4-chloro-pyrimidine

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With sodium hydroxide In water at 80℃; for 4h;93%
5-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil

5-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With sulfuric acid In water at 80℃; for 7h;93%
5-fluoro-6-chlorouracil
13593-36-7

5-fluoro-6-chlorouracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With acetic acid; zinc at 100℃; for 5h; var.: reag.: hydrogen, Et3N or NaOH, cat.: Pd/C, in EtOH, RT;91%
uracil
66-22-8

uracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With C19XeF6 In dichloromethane for 24h; Ambient temperature;90%
With fluorine; trifluoroacetic acid at -10℃; under 2250.23 Torr; Reagent/catalyst; Temperature; Pressure; Inert atmosphere;89.4%
81.4%
1,3-dimethyl-5-azauracil
824-28-2

1,3-dimethyl-5-azauracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With fluoroacetamide; lithium diisopropyl amide In diethyl ether at 0℃; for 4h;88%
With fluoroacetamide; lithium diisopropyl amide In diethyl ether at 0℃; for 4h; a novel ring transformation reaction;88%
fluorine fluorosulfonate

fluorine fluorosulfonate

Cytosine
71-30-7

Cytosine

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
In water87.7%
trifluoromethyl hypofluorite (CF3 OF)

trifluoromethyl hypofluorite (CF3 OF)

2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid monohydrate

2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid monohydrate

A

5-fluorouracil
51-21-8

5-fluorouracil

B

5-fluoroorotic acid hydrate
220141-70-8

5-fluoroorotic acid hydrate

Conditions
ConditionsYield
In trichloromonofluoromethane (CFCl3); water; trifluoroacetic acid; PolytetrafluoroethyleneA n/a
B 86%
2,4-dimethoxy-5-fluoropyrimidine
4330-22-7

2,4-dimethoxy-5-fluoropyrimidine

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With hydrogenchloride81.3%
N1,N3-dibenzyl-5-fluorouracil
75500-02-6

N1,N3-dibenzyl-5-fluorouracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With boron tribromide In various solvent(s) at 138℃; for 24h;80%
Cytosine
71-30-7

Cytosine

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With trifluoroacetic acid In water80%
With calcium hydroxide In hydrogen fluoride; water76.2%
In water67%
2-methoxy-5-fluorouracil
1480-96-2

2-methoxy-5-fluorouracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With hydrogenchloride In methanol at 28℃; for 5h; Temperature;78.3%
With hydrogenchloride In water at 55℃; for 3h; Large scale;65.24 kg
C18H15FN4O6S2
1141462-25-0

C18H15FN4O6S2

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With Enterobacter cloacae β-lactamase for 20h; pH=7.0; aq. phosphate buffer;78%
Cytosine
71-30-7

Cytosine

sodium hydrogensulfite

sodium hydrogensulfite

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
In water75.4%
2-[2-(5-Fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-isopropoxy-ethyl]-isoindole-1,3-dione
98224-73-8

2-[2-(5-Fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-isopropoxy-ethyl]-isoindole-1,3-dione

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With L-valine In acetic acid71%
(Z)-N-(2-fluoro-3-methoxyprop-2-enoyl)urea

(Z)-N-(2-fluoro-3-methoxyprop-2-enoyl)urea

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With sodium hydroxide at 80℃; for 1h;67%
Cytosine hydrochloride
1784-08-3

Cytosine hydrochloride

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
In water66%
5-fluoro-6-hydroxy-5-methoxycarbonyl-5,6-dihydrouracil
65726-47-8

5-fluoro-6-hydroxy-5-methoxycarbonyl-5,6-dihydrouracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With hydrogenchloride In water for 1h; Heating;65%
(4R,5R)-4-Butoxy-5-fluoro-2,6-dioxo-hexahydro-pyrimidine-5-carboxylic acid ethyl ester
65906-75-4, 76481-58-8, 81033-59-2, 84471-52-3, 84471-53-4

(4R,5R)-4-Butoxy-5-fluoro-2,6-dioxo-hexahydro-pyrimidine-5-carboxylic acid ethyl ester

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With hydrogenchloride for 1h; Product distribution; Heating; variation of reagent, temperature; in ethanol;62%
1,3-bis-((benzyloxy)methyl)-5-fluoropyrimidine-2,4(1H,3H)-dione
75500-03-7

1,3-bis-((benzyloxy)methyl)-5-fluoropyrimidine-2,4(1H,3H)-dione

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With boron tribromide In benzene for 1h; Ambient temperature;60%
With trimethylsilyl iodide; water 1.) chloroform, reflux, 6 h, 2.) reflux, 30 min; 160-180 deg C, 15 min; reflux; Yield given. Multistep reaction;
5-methoxycarbonyluracil

5-methoxycarbonyluracil

A

5-fluorouracil
51-21-8

5-fluorouracil

B

5-chloro-5-fluoro-6-hydroxy-5,6-dihydrouracil
58532-67-5

5-chloro-5-fluoro-6-hydroxy-5,6-dihydrouracil

Conditions
ConditionsYield
With hydrogenchloride; fluorine In water for 1.16667h; Heating;A 59%
B 14%
(+/-)-cis-6-butoxy-5-fluoro-5,6-dihydrouracil
1134-30-1, 77449-87-7, 81033-60-5, 83409-64-7

(+/-)-cis-6-butoxy-5-fluoro-5,6-dihydrouracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With hydrogenchloride for 1h; Product distribution; Heating; variation of reagent, temperature; in ethanol;48%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine
17242-85-2

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine

A

5-fluorouracil
51-21-8

5-fluorouracil

B

tegafur
17902-23-7

tegafur

Conditions
ConditionsYield
With pyridine hydrochloride In chloroform at 60 - 70℃; Product distribution; other temperature, other solvents;A 0.6 g
B 44.5%
5-fluoro-6-butoxy-5,6-dihydrouracil
1134-30-1, 77449-87-7, 81033-60-5, 83409-64-7

5-fluoro-6-butoxy-5,6-dihydrouracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With hydrogenchloride for 1h; Product distribution; Heating; variation of reagent, temperature; in ethanol;42%
at 150℃; sublimation under cacuum; Yield given;
5-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil
1005-80-7, 1005-82-9, 1820-76-4

5-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With acetic anhydride at 140℃; for 5h;40%
2-[2-(5-Fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-methoxy-ethyl]-isoindole-1,3-dione
98224-77-2

2-[2-(5-Fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-methoxy-ethyl]-isoindole-1,3-dione

5-fluorouracil
51-21-8

5-fluorouracil

Conditions
ConditionsYield
With L-valine In acetic acid38%
formaldehyd
50-00-0

formaldehyd

5-fluorouracil
51-21-8

5-fluorouracil

N1,N3-bis(hydroxymethyl)-5-fluorouracil
74179-14-9

N1,N3-bis(hydroxymethyl)-5-fluorouracil

Conditions
ConditionsYield
With water at 60℃; for 6h;100%
In water at 70℃; for 0.25h; Yield given;
at 60℃; for 0.75h;
5-fluorouracil
51-21-8

5-fluorouracil

Succinic semialdehyde
692-29-5

Succinic semialdehyde

tegafur
17902-23-7

tegafur

Conditions
ConditionsYield
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In tetrahydrofuran at 15 - 20℃; for 12h; Solvent; Reagent/catalyst; Temperature;99.8%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

5-fluorouracil
51-21-8

5-fluorouracil

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine
17242-85-2

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexamethyl-disilazane Ambient temperature;99%
With 1,1,1,3,3,3-hexamethyl-disilazane
With 1,1,1,3,3,3-hexamethyl-disilazane at 140 - 150℃; for 5h;
5-fluorouracil
51-21-8

5-fluorouracil

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1-tert-butyl 5-fluoro-2,4-dioxone-3,4-dihydropyrimidine-1(2H)-carboxylate
402849-04-1

1-tert-butyl 5-fluoro-2,4-dioxone-3,4-dihydropyrimidine-1(2H)-carboxylate

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 19h; Inert atmosphere;99%
With dmap In acetonitrile at 20℃; for 3h;92%
With dmap78%
5-fluorouracil
51-21-8

5-fluorouracil

3,5-di-O-p-methoxybenzoyl-2-deoxy-D-ribofuranosyl ortho-hexynylbenzoate

3,5-di-O-p-methoxybenzoyl-2-deoxy-D-ribofuranosyl ortho-hexynylbenzoate

5-fluoro-1-(3',5'-di-O-p-methoxybenzoyl-2'-deoxy-D-ribofuranosyl)uracil
1384553-43-8

5-fluoro-1-(3',5'-di-O-p-methoxybenzoyl-2'-deoxy-D-ribofuranosyl)uracil

Conditions
ConditionsYield
Stage #1: 5-fluorouracil; 3,5-di-O-p-methoxybenzoyl-2-deoxy-D-ribofuranosyl ortho-hexynylbenzoate With N,O-Bis(trimethylsilyl)trifluoroacetamide In acetonitrile at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In 1,2-dichloro-ethane at 20℃; for 12h; Molecular sieve; diastereoselective reaction;
99%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

5-fluorouracil
51-21-8

5-fluorouracil

tegafur
17902-23-7

tegafur

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II); tris(2,2′-bipyridine)ruthenium(II) bis(tetrafluoroborate) In tetrahydrofuran at 25 - 30℃; Temperature; Solvent; Wavelength; Reagent/catalyst; Irradiation;98.7%
With calcium chloride; trifluoroacetic acid In chloroform; N,N-dimethyl-formamide; toluene85.2%
With dimethylmonochlorosilane; triethylamine In acetonitrile at 16℃; Temperature;85%
5-fluorouracil
51-21-8

5-fluorouracil

1,1,1,2,2,2-hexamethyldisilane
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine
17242-85-2

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine

Conditions
ConditionsYield
With ammonium sulfate for 14h; Heating;98%
5-fluorouracil
51-21-8

5-fluorouracil

parabanic acid
120-89-8

parabanic acid

Conditions
ConditionsYield
With oxygen; ozone In acetic acid at 20℃; for 0.75h;98%
With oxygen; ozone In acetic acid at 20℃; for 0.75h; Product distribution;98%
5-fluorouracil
51-21-8

5-fluorouracil

1-adamantyl bromomethyl ketone
5122-82-7

1-adamantyl bromomethyl ketone

1-<2-(1-adamantyl)-2-oxo-ethyl>-5-fluorouracide

1-<2-(1-adamantyl)-2-oxo-ethyl>-5-fluorouracide

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 22h;98%
5-fluorouracil
51-21-8

5-fluorouracil

C34H28O7

C34H28O7

2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine
77180-87-1

2',3'-di-O-benzoyl-5'-deoxy-5-fluorouridine

Conditions
ConditionsYield
Stage #1: 5-fluorouracil With N,O-Bis(trimethylsilyl)trifluoroacetamide In acetonitrile at 50℃; for 0.5h; Inert atmosphere;
Stage #2: C34H28O7 In acetonitrile at 20℃; for 0.75h; Inert atmosphere; Molecular sieve;
Stage #3: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 20℃; for 2h; Inert atmosphere; Molecular sieve;
98%
5-fluorouracil
51-21-8

5-fluorouracil

micheliolide

micheliolide

C19H23FN2O5

C19H23FN2O5

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; Inert atmosphere;97.5%
5-fluorouracil
51-21-8

5-fluorouracil

2-chloro-ethanol
107-07-3

2-chloro-ethanol

A

3-(2-hydroxyethyl)-5-fluorouracil

3-(2-hydroxyethyl)-5-fluorouracil

B

5-Fluoro-1,3-bis(2-hydroxyethyl)-uracil
55185-82-5

5-Fluoro-1,3-bis(2-hydroxyethyl)-uracil

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water Heating;A 3%
B 97%
5-fluorouracil
51-21-8

5-fluorouracil

benzyl bromide
100-39-0

benzyl bromide

N1,N3-dibenzyl-5-fluorouracil
75500-02-6

N1,N3-dibenzyl-5-fluorouracil

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide96%
With potassium carbonate In N,N-dimethyl-formamide Ambient temperature;
With potassium hydroxide; tetrabutylammomium bromide 1.) 80 deg C, 2 h, 2.) 1 h; Yield given. Multistep reaction;
5-fluorouracil
51-21-8

5-fluorouracil

N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium p-toluenesulfonate
92641-15-1

N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium p-toluenesulfonate

1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil
81820-68-0, 104861-73-6, 104889-91-0

1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 15h; Ambient temperature;96%
5-fluorouracil
51-21-8

5-fluorouracil

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

3-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid methyl ester

3-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid methyl ester

Conditions
ConditionsYield
With lipozyme Thermomyces lanuginosus IM In dimethyl sulfoxide at 50℃; for 0.5h; Michael Addition; Flow reactor; Enzymatic reaction;96%
With triethylamine In N,N-dimethyl-formamide at 60℃; Aza-Micheal reaction;95%
With triethylamine In N,N-dimethyl-formamide at 60℃; for 4h; Michael Addition;95%
5-fluorouracil
51-21-8

5-fluorouracil

vinyl acrylate
2177-18-6

vinyl acrylate

3-(5-fluorouracil-1-yl)propionic acid vinyl ester
884308-97-8

3-(5-fluorouracil-1-yl)propionic acid vinyl ester

Conditions
ConditionsYield
With D-aminoacylase from Escherichia coli In dimethyl sulfoxide at 25℃; for 0.416667h; Michael addition; Enzymatic reaction; regioselective reaction;96%
5-fluorouracil
51-21-8

5-fluorouracil

tetrahydrofuran-2-yl benzoate
3333-44-6

tetrahydrofuran-2-yl benzoate

tegafur
17902-23-7

tegafur

Conditions
ConditionsYield
With sodium acetate; tetra-(n-butyl)ammonium iodide In dichloromethane; water at 35℃; for 2h; Solvent; Temperature; Reagent/catalyst;95.2%
5-fluorouracil
51-21-8

5-fluorouracil

N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium chloride
92641-11-7

N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium chloride

1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil
81820-68-0, 104861-73-6, 104889-91-0

1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide for 15h; Ambient temperature;95%
5-fluorouracil
51-21-8

5-fluorouracil

N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium methanesulfonate
92641-14-0

N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium methanesulfonate

1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil
81820-68-0, 104861-73-6, 104889-91-0

1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 15h; Ambient temperature;95%
5-fluorouracil
51-21-8

5-fluorouracil

N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium trifluoroacetate
92641-17-3

N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium trifluoroacetate

1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil
81820-68-0, 104861-73-6, 104889-91-0

1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 15h; Ambient temperature;95%
methanol
67-56-1

methanol

5-fluorouracil
51-21-8

5-fluorouracil

5-chloro-5-fluoro-6-methoxy-5,6-dihydrouracil

5-chloro-5-fluoro-6-methoxy-5,6-dihydrouracil

Conditions
ConditionsYield
With chlorine at 20℃; for 2h;95%
With N-chloro-succinimide at 50℃;91%
5-fluorouracil
51-21-8

5-fluorouracil

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

1-(2,4-dinitro-phenyl)-5-fluoro-1H-pyrimidine-2,4-dione

1-(2,4-dinitro-phenyl)-5-fluoro-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
With zinc(II) oxide at 130℃; for 0.1h; Ionic liquid; Microwave irradiation;95%
With tetrabutylammomium bromide; silica gel; caesium carbonate for 0.416667h; Heating;83%
With silica gel; caesium carbonate In dimethyl sulfoxide for 0.0333333h; microwave irradiation;82%
5-fluorouracil
51-21-8

5-fluorouracil

5-fluoro-6-hydroxy-5-nitro-5,6-dihydrouracil

5-fluoro-6-hydroxy-5-nitro-5,6-dihydrouracil

Conditions
ConditionsYield
With sulfuric acid; nitric acid In water at 0 - 10℃;95%
5-fluorouracil
51-21-8

5-fluorouracil

5-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil

5-bromo-5-fluoro-6-hydroxy-5,6-dihydrouracil

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; potassium bromide In water at 20℃;95%
5-fluorouracil
51-21-8

5-fluorouracil

propyl bromide
106-94-5

propyl bromide

5-Fluoro-1,3-dipropyl-1H-pyrimidine-2,4-dione
89501-11-1

5-Fluoro-1,3-dipropyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide In dichloromethane Ambient temperature;94%
5-fluorouracil
51-21-8

5-fluorouracil

4-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-4-methyl morpholinium bromide
92641-10-6

4-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-4-methyl morpholinium bromide

1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil
81820-68-0, 104861-73-6, 104889-91-0

1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide for 15h; Ambient temperature;94%

5-Fluorouracil Chemical Properties

Molecular structure of Fluorouracil (CAS NO.51-21-8) is:

Product Name: Fluorouracil
CAS Registry Number: 51-21-8
IUPAC Name: 5-fluoro-1H-pyrimidine-2,4-dione
Molecular Weight: 130.077223 [g/mol]
Molecular Formula: C4H3FN2O2
XLogP3: -0.9
H-Bond Donor: 2
H-Bond Acceptor: 3 
EINECS: 200-085-6
Melting Point: 282-286 °C (dec.)(lit.)
Surface Tension: 46.1 dyne/cm
Density: 1.53 g/cm3
Flash Point: 196.5 °C
Enthalpy of Vaporization: 67.78 kJ/mol
Boiling Point: 401.4 °C at 760 mmHg
Vapour Pressure: 5.13E-07 mmHg at 25°C 
Water Solubility: 12.2 g/L 20 °C
Sensitive: Air Sensitive
Stability: Stable. Light sensitive. Combustible. Incompatible with strong oxidizing agents, strong bases.
Product Categories: Pharmaceutical Raw Materials;PYRIMIDINE;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;Phenylacetic acid;Tegafur Carmofur;Nucleotides and Nucleosides;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Nucleotides;API's;Antitumour

5-Fluorouracil History

 Fluorouracil (CAS NO.51-21-8) was synthesized by Robert Duschinsky in the late 1950s.

5-Fluorouracil Uses

 Fluorouracil (CAS NO.51-21-8) can be used in against cancer for about 40 years, acts in several ways, but principally as a thymidylate synthase inhibitor. It can be used in colorectal cancer and pancreatic cancer,also it can be used for treating actinic (solar) keratoses and some types of basal cell carcinomas of the skin.

5-Fluorouracil Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 30mg/kg (30mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Oyo Yakuri. Pharmacometrics. Vol. 16, Pg. 303, 1978.
guinea pig LD50 intravenous 25mg/kg (25mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION Japanese Journal of Pharmacology. Vol. 30, Pg. 871, 1980.
hamster LD10 parenteral 140mg/kg (140mg/kg)   Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.
human TDLo intravenous 6mg/kg/3D (6mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
British Medical Journal. Vol. 1, Pg. 547, 1978.
human TDLo oral 450mg/kg/30D (450mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Cancer Vol. 39, Pg. 1936, 1977.
man TDLo intravenous 39mg/kg/1D-I (39mg/kg) CARDIAC: CHANGES IN CORONARY ARTERIES American Heart Journal. Vol. 114, Pg. 433, 1987.
man TDLo intravenous 122mg/kg/9W-I (122mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Australian and New Zealand Journal of Medicine. Vol. 22, Pg. 385, 1992.
mouse LD50 intracrebral 41600ug/kg (41.6mg/kg) PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Chemotherapy Vol. 15, Pg. 519, 1967.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 7, Pg. 100, 1977.
mouse LD50 intravenous 81mg/kg (81mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
mouse LD50 oral 115mg/kg (115mg/kg)   Journal of Medicinal Chemistry. Vol. 21, Pg. 738, 1978.
mouse LD50 subcutaneous 169mg/kg (169mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
mouse LD50 unreported 171mg/kg (171mg/kg)   Cancer Research. Vol. 46, Pg. 2703, 1986.
mouse LDLo intratracheal 200mg/kg (200mg/kg)   Toxicology Letters. Vol. 30, Pg. 63, 1986.
rabbit LD50 oral 18900ug/kg (18.9mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Kiso to Rinsho. Clinical Report. Vol. 8, Pg. 2603, 1974.
rabbit LDLo intravenous 15mg/kg (15mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION Japanese Journal of Pharmacology. Vol. 30, Pg. 871, 1980.
rat LD50 intramuscular 240mg/kg (240mg/kg)   K'at'ollik Taehak Uihakpu Nonmunjip. Journal of Catholic Medical College. Vol. 38, Pg. 481, 1985.
rat LD50 intraperitoneal 70mg/kg (70mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 569, 1971.
rat LD50 intravenous 245mg/kg (245mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 569, 1971.
rat LD50 oral 230mg/kg (230mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
rat LD50 parenteral 500mg/kg (500mg/kg)   Recent Results in Cancer Research. Vol. 52, Pg. 76, 1975.
rat LD50 rectal 884mg/kg (884mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: OTHER CHANGES
Kiso to Rinsho. Clinical Report. Vol. 12, Pg. 1309, 1978.
rat LD50 subcutaneous 217mg/kg (217mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 90, 1973.
women TDLo intravenous 27mg/kg/4D-C (27mg/kg) CARDIAC: OTHER CHANGES British Medical Journal. Vol. 294, Pg. 125, 1987.
women TDLo intravenous 150mg/kg/17W- (150mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA British Journal of Haematology. Vol. 65, Pg. 357, 1987.

5-Fluorouracil Safety Profile

Hazard Codes: HarmfulXn,Xi ;ToxicT;CorrosiveC
Risk Statements: 20/21/22 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36/37/39-22 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S22: Do not breathe dust.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: YR0350000
F: 10-23
Hazard Note: Irritant/Highly Toxic
TSCA: T
HazardClass: 6.1
PackingGroup: III
HS Code: 29335995

5-Fluorouracil Specification

 Fluorouracil , its cas register number is 51-21-8. It also can be called 2,4(1H,3H)-Pyrimidinedione, 5-fluoro- ; 2,4-Dioxo-5-fluoropyrimidine ; 5-FU ; 5-Faracil ; 5-Fluor-2,4(1H,3H)-pyrimidindion ; 5-Fluor-2,4-dihydroxypyrimidin .It is a white to nearly white crystalline powder and insoluble in water.

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