trans-5-fluoro-6-acetoxy-5,6-dihydrouracil
5-fluorouracil
Conditions | Yield |
---|---|
With triethylamine at 60℃; | 100% |
(+/-)-t-6-butoxy-r-5-ethoxycarbonyl-5-fluoro-5,6-dihydrouracil
5-fluorouracil
Conditions | Yield |
---|---|
With hydrogenchloride for 1h; Product distribution; Heating; variation of reagent, temperature; in ethanol; | 95% |
methyl 5-fluoro-4-methoxy-2,6-dioxohexahydro-5-pyrimidinecarboxylate
5-fluorouracil
Conditions | Yield |
---|---|
With hydrogenchloride In water for 2.5h; | 95% |
2,5-difluoro-4-chloro-pyrimidine
5-fluorouracil
Conditions | Yield |
---|---|
With sodium hydroxide In water at 80℃; for 4h; | 93% |
5-fluorouracil
Conditions | Yield |
---|---|
With sulfuric acid In water at 80℃; for 7h; | 93% |
5-fluoro-6-chlorouracil
5-fluorouracil
Conditions | Yield |
---|---|
With acetic acid; zinc at 100℃; for 5h; var.: reag.: hydrogen, Et3N or NaOH, cat.: Pd/C, in EtOH, RT; | 91% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In water | 87.7% |
A
5-fluorouracil
B
5-fluoroorotic acid hydrate
Conditions | Yield |
---|---|
In trichloromonofluoromethane (CFCl3); water; trifluoroacetic acid; Polytetrafluoroethylene | A n/a B 86% |
Conditions | Yield |
---|---|
With hydrogenchloride | 81.3% |
N1,N3-dibenzyl-5-fluorouracil
5-fluorouracil
Conditions | Yield |
---|---|
With boron tribromide In various solvent(s) at 138℃; for 24h; | 80% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In water | 80% |
With calcium hydroxide In hydrogen fluoride; water | 76.2% |
In water | 67% |
Conditions | Yield |
---|---|
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
5-fluorouracil
Conditions | Yield |
---|---|
With Enterobacter cloacae β-lactamase for 20h; pH=7.0; aq. phosphate buffer; | 78% |
Conditions | Yield |
---|---|
In water | 75.4% |
2-[2-(5-Fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-isopropoxy-ethyl]-isoindole-1,3-dione
5-fluorouracil
Conditions | Yield |
---|---|
With L-valine In acetic acid | 71% |
5-fluorouracil
Conditions | Yield |
---|---|
With sodium hydroxide at 80℃; for 1h; | 67% |
Conditions | Yield |
---|---|
In water | 66% |
5-fluoro-6-hydroxy-5-methoxycarbonyl-5,6-dihydrouracil
5-fluorouracil
Conditions | Yield |
---|---|
With hydrogenchloride In water for 1h; Heating; | 65% |
(4R,5R)-4-Butoxy-5-fluoro-2,6-dioxo-hexahydro-pyrimidine-5-carboxylic acid ethyl ester
5-fluorouracil
Conditions | Yield |
---|---|
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
5-fluorouracil
Conditions | Yield |
---|---|
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; |
A
5-fluorouracil
B
5-chloro-5-fluoro-6-hydroxy-5,6-dihydrouracil
Conditions | Yield |
---|---|
With hydrogenchloride; fluorine In water for 1.16667h; Heating; | A 59% B 14% |
(+/-)-cis-6-butoxy-5-fluoro-5,6-dihydrouracil
5-fluorouracil
Conditions | Yield |
---|---|
With hydrogenchloride for 1h; Product distribution; Heating; variation of reagent, temperature; in ethanol; | 48% |
2,3-dihydro-2H-furan
5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine
A
5-fluorouracil
B
tegafur
Conditions | Yield |
---|---|
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
5-fluorouracil
Conditions | Yield |
---|---|
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
5-fluorouracil
Conditions | Yield |
---|---|
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
5-fluorouracil
Conditions | Yield |
---|---|
With L-valine In acetic acid | 38% |
Conditions | Yield |
---|---|
With water at 60℃; for 6h; | 100% |
In water at 70℃; for 0.25h; Yield given; | |
at 60℃; for 0.75h; |
Conditions | Yield |
---|---|
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
5-fluorouracil
5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine
Conditions | Yield |
---|---|
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
di-tert-butyl dicarbonate
1-tert-butyl 5-fluoro-2,4-dioxone-3,4-dihydropyrimidine-1(2H)-carboxylate
Conditions | Yield |
---|---|
With dmap In acetonitrile at 20℃; for 19h; Inert atmosphere; | 99% |
With dmap In acetonitrile at 20℃; for 3h; | 92% |
With dmap | 78% |
5-fluorouracil
5-fluoro-1-(3',5'-di-O-p-methoxybenzoyl-2'-deoxy-D-ribofuranosyl)uracil
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; toluene | 85.2% |
With dimethylmonochlorosilane; triethylamine In acetonitrile at 16℃; Temperature; | 85% |
5-fluorouracil
1,1,1,2,2,2-hexamethyldisilane
5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine
Conditions | Yield |
---|---|
With ammonium sulfate for 14h; Heating; | 98% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 22h; | 98% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 20℃; Inert atmosphere; | 97.5% |
5-fluorouracil
2-chloro-ethanol
B
5-Fluoro-1,3-bis(2-hydroxyethyl)-uracil
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water Heating; | A 3% B 97% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 96% |
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
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
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 15h; Ambient temperature; | 96% |
5-fluorouracil
acrylic acid methyl ester
Conditions | Yield |
---|---|
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
vinyl acrylate
3-(5-fluorouracil-1-yl)propionic acid vinyl ester
Conditions | Yield |
---|---|
With D-aminoacylase from Escherichia coli In dimethyl sulfoxide at 25℃; for 0.416667h; Michael addition; Enzymatic reaction; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
With sodium acetate; tetra-(n-butyl)ammonium iodide In dichloromethane; water at 35℃; for 2h; Solvent; Temperature; Reagent/catalyst; | 95.2% |
5-fluorouracil
N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium chloride
1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil
Conditions | Yield |
---|---|
With triethylamine In dimethyl sulfoxide for 15h; Ambient temperature; | 95% |
5-fluorouracil
N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium methanesulfonate
1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 15h; Ambient temperature; | 95% |
5-fluorouracil
N-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-N,N,N-triethyl ammonium trifluoroacetate
1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 15h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With chlorine at 20℃; for 2h; | 95% |
With N-chloro-succinimide at 50℃; | 91% |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid In water at 0 - 10℃; | 95% |
5-fluorouracil
Conditions | Yield |
---|---|
With sulfuric acid; dihydrogen peroxide; potassium bromide In water at 20℃; | 95% |
5-fluorouracil
propyl bromide
5-Fluoro-1,3-dipropyl-1H-pyrimidine-2,4-dione
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydroxide In dichloromethane Ambient temperature; | 94% |
5-fluorouracil
4-(1,3-dihydro-3-oxoisobenzofuran-1-yl)-4-methyl morpholinium bromide
1-(3-oxo-1,3-dihydro-1-isobenzofuranyl)-5-fluorouracil
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide for 15h; Ambient temperature; | 94% |
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
Fluorouracil (CAS NO.51-21-8) was synthesized by Robert Duschinsky in the late 1950s.
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.
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. |
Hazard Codes: Xn,Xi ;T;C
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
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.
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View