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Trifluridine
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Name

Trifluridine

 EINECS 200-722-8
CAS No. 70-00-8 Density 1.646 g/cm3
PSA 104.55000 LogP -0.80390
Solubility N/A Melting Point 190-193 °C(lit.)
Formula C10H11F3N2O5 Boiling Point N/A
Molecular Weight 296.203 Flash Point N/A
Transport Information N/A Appearance Almost white crystalline power
Safety 22-36 Risk Codes 20/21/22-40
Molecular Structure Molecular Structure of 70-00-8 (Trifluridine) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

Uridine, 2'-deoxy-5-(trifluoromethyl)-(7CI);2'-Deoxy-5-(trifluoromethyl)uridine;5-(Trifluoromethyl)-2'-deoxyuridine;5-(Trifluoromethyl)deoxyuridine;5-Trifluoromethyl-2'-deoxy-b-uridine;5-Trifluorothymidine;NSC 529182;NSC 75520;Trifluorothymidine;Viroptic;

Article Data 32

Trifluridine Synthetic route

C24H17Cl2F3N2O7

70-00-8

2'-deoxy-5-trifluoromethyluridine

Conditions
ConditionsYield
With methanol; sodium methylate at 4 - 6℃; for 3.5h;97%
65499-42-5

5-trifluoromethyl-2′-deoxyuridine-3′,5′-diacetate

70-00-8

2'-deoxy-5-trifluoromethyluridine

Conditions
ConditionsYield
With ammonia In methanol at 20℃;95%
With ammonia In methanol at 0 - 20℃; for 16h;84%
With ammonia In methanol at 20℃; for 19h;76%
951-78-0

2'-deoxyuridine

2926-29-6

Langlois reagent

70-00-8

2'-deoxy-5-trifluoromethyluridine

Conditions
ConditionsYield
With tert.-butylhydroperoxide In water at -3 - 60℃; for 2h; Temperature; Inert atmosphere;94.3%
With tert.-butylhydroperoxide In water at -5 - 65℃; for 3h; Inert atmosphere; Large scale;94.8%
With tert-butyl alcohol In water at 0 - 20℃; for 3h;59%
With mesoporous graphitic carbon nitride In dimethyl sulfoxide at 25℃; Irradiation;47%
With acetone In water at 20℃; for 40h; UV-irradiation; Inert atmosphere;44%
21618-67-7

5-(trifluoromethyl)uridine

70-00-8

2'-deoxy-5-trifluoromethyluridine

Conditions
ConditionsYield
Stage #1: 5-(trifluoromethyl)uridine With sodium hydrogencarbonate; carbonic acid dimethyl ester In N,N-dimethyl-formamide at 120℃; for 8h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 55℃; for 10h;
Stage #3: With palladium on activated charcoal; hydrogen; sodium hydroxide In water; N,N-dimethyl-formamide at 15℃; under 4500.45 Torr; for 12h; pH=7 - 8;		86.4%
129664-47-7

1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-erythro-pentofuranosyl>-5-trifluoromethyluracil

70-00-8

2'-deoxy-5-trifluoromethyluridine

Conditions
ConditionsYield
With sodium methylate In methanol at 20 - 30℃; for 4h;82.5%
With methanol; sodium methylate for 1h; Ambient temperature;67%
65499-42-5

3',5'-di-O-acetyl-5-(trifluoromethyl)-2'-deoxyuridine

70-00-8

2'-deoxy-5-trifluoromethyluridine

Conditions
ConditionsYield
With ammonia In methanol for 10h; Ambient temperature;82%
887144-94-7

Togni's reagent II

951-78-0

2'-deoxyuridine

70-00-8

2'-deoxy-5-trifluoromethyluridine

Conditions
ConditionsYield
With copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 23h; Inert atmosphere; Sealed tube; regioselective reaction;76%
2314-97-8

iodotrifluoromethane

951-78-0

2'-deoxyuridine

70-00-8

2'-deoxy-5-trifluoromethyluridine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide for 24h; Inert atmosphere; Irradiation;71%
With caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;68%
With iron(III) sulfate; sulfuric acid; dihydrogen peroxide In water; dimethyl sulfoxide at 40 - 50℃; for 0.333333h;58%
76513-99-0

5-(trifluoromethyl)-3',5'-di-O-trityl-2'-deoxyuridine

70-00-8

2'-deoxy-5-trifluoromethyluridine

Conditions
ConditionsYield
With formic acid at 0℃; for 0.0166667h;40%
89143-01-1

Hexanoic acid (2R,3S,5R)-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-2-hexanoyloxymethyl-tetrahydro-furan-3-yl ester

A

89143-05-5

5'-O-hexanoyl-2'-deoxy-5-trifluoromethyluridine

B

70-00-8

2'-deoxy-5-trifluoromethyluridine

Conditions
ConditionsYield
With phosphate buffer In N,N-dimethyl-formamide at 25℃; for 18h; enzym: Pseudomonas fluorescens;A 62 % Chromat.
B 6 % Chromat.

Trifluridine Chemical Properties

IUPAC Name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl) pyrimidine-2,4-dione 
Empirical Formula: C10H11F3N2O5
Molecular Weight: 296.1999g/mol
EINECS: 200-722-8 
Structure of Trifluridine (CAS NO.70-00-8):

Index of Refraction: 1.534
Molar Refractivity: 55.92 cm3
Molar Volume: 179.8 cm3
Polarizability: 22.17×10-24cm3
Surface Tension: 56.1 dyne/cm
Density: 1.646 g/cm3 
Melting Point: 190-193 °C(lit.)
Product Categories: Pharmaceutical Raw Materials;Pyrimidine series;API intermediates;Nucleotides and Nucleosides;Antivirals for Research and Experimental Use;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Nucleotides 
Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)C(F)(F)F)CO)O
Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)C(F)(F)F)CO)O
InChI: InChI=1S/C10H11F3N2O5/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7/h2,5-7,16-17H,1,3H2,(H,14,18,19)/t5-,6+,7+/m0/s1
InChIKey: VSQQQLOSPVPRAZ-RRKCRQDMSA-N

Trifluridine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
monkey LDLo intravenous 400mg/kg (400mg/kg)   Government Reports Announcements. Vol. 74(9), Pg. 60, 1974.
mouse LD50 intraperitoneal 1931mg/kg (1931mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 3381mg/kg (3381mg/kg)   Progress Report Submitted to the National Cancer Institute by Arthur D. Little, Inc. Vol. -, Pg. 260, 1967.
rat LD50 intravenous 2946mg/kg (2946mg/kg) LIVER: OTHER CHANGES Progress Report Submitted to the National Cancer Institute by Arthur D. Little, Inc. Vol. -, Pg. 260, 1967.

Trifluridine Safety Profile

Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 20/21/22-40
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 22-36
S22:Do not breathe dust. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: XP2087500
Hazard Note: Keep Cold

Trifluridine Specification

  Trifluridine , its cas register number is 70-00-8. It also can be called 2'-Deoxy-5-(trifluoromethyl)uridine ; 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-ribofuranosyl)-5-(trifluoromethyl)- ; 5-(Trifluoromethyl)deoxyuridine ; 5-Trifluoro-2'-deoxythymidine ; 5-Trifluoromethyl-2-deoxyuridine ; F3DThd ; F3T ; F3TDR ; NSC 529182 ; NSC 75520 ; TFDU ;
 Trifluoromethyldeoxyuridine ; Trifluorothymidine ; Trifluridina ; Trifluridine ; Trifluridinum ; UNII-RMW9V5RW38 ; Uridine, 2'-deoxy-5-(trifluoromethyl)- ; Viroptic .

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