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51-21-8

Basic Information
CAS No.: 51-21-8
Name: 5-Fluorouracil
Article Data: 130
Molecular Structure:
Molecular Structure of 51-21-8 (5-Fluorouracil)
Formula: C4H3FN2O2
Molecular Weight: 130.078
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;
EINECS: 200-085-6
Density: 1.53 g/cm3
Melting Point: 282-286 °C (dec.)(lit.)
Boiling Point: 401.4 °C at 760 mmHg
Flash Point: 196.5 °C
Solubility: insoluble in water white to nearly white crystalline powder
Hazard Symbols: HarmfulXn,ToxicT,CorrosiveC,IrritantXi
Risk Codes: 22-20/21/22
Safety: 36-36/37-36/37/39-22
Transport Information: UN 2811 6.1/PG 3
PSA: 65.72000
LogP: -0.79770
Synthetic route
56311-36-5, 100814-55-9, 100814-58-2

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

51-21-8

5-fluorouracil

Conditions
ConditionsYield
With triethylamine at 60℃;100%
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

51-21-8

5-fluorouracil

Conditions
ConditionsYield
With hydrogenchloride for 1h; Product distribution; Heating; variation of reagent, temperature; in ethanol;95%
65905-96-6

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

51-21-8

5-fluorouracil

Conditions
ConditionsYield
With hydrogenchloride In water for 2.5h;95%
99429-06-8

2,5-difluoro-4-chloro-pyrimidine

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

51-21-8

5-fluorouracil

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

5-fluoro-6-chlorouracil

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%
66-22-8

uracil

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%
824-28-2

1,3-dimethyl-5-azauracil

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

71-30-7

Cytosine

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

A

51-21-8

5-fluorouracil

B

220141-70-8

5-fluoroorotic acid hydrate

Conditions
ConditionsYield
In trichloromonofluoromethane (CFCl3); water; trifluoroacetic acid; PolytetrafluoroethyleneA n/a
B 86%
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Chemistry

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

History

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

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.

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.

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

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.