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CAS No.: | 70-00-8 |
---|---|
Name: | Trifluridine |
Article Data: | 32 |
Molecular Structure: | |
Formula: | C10H11F3N2O5 |
Molecular Weight: | 296.203 |
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; |
EINECS: | 200-722-8 |
Density: | 1.646 g/cm3 |
Melting Point: | 190-193 °C(lit.) |
Appearance: | Almost white crystalline power |
Hazard Symbols: | Xn, Xi |
Risk Codes: | 20/21/22-40 |
Safety: | 22-36 |
PSA: | 104.55000 |
LogP: | -0.80390 |
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With methanol; sodium methylate at 4 - 6℃; for 3.5h; | 97% |
5-trifluoromethyl-2′-deoxyuridine-3′,5′-diacetate
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
5-(trifluoromethyl)uridine
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
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% |
1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-erythro-pentofuranosyl>-5-trifluoromethyluracil
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With sodium methylate In methanol at 20 - 30℃; for 4h; | 82.5% |
With methanol; sodium methylate for 1h; Ambient temperature; | 67% |
3',5'-di-O-acetyl-5-(trifluoromethyl)-2'-deoxyuridine
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With ammonia In methanol for 10h; Ambient temperature; | 82% |
Conditions | Yield |
---|---|
With copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 23h; Inert atmosphere; Sealed tube; regioselective reaction; | 76% |
Conditions | Yield |
---|---|
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% |
5-(trifluoromethyl)-3',5'-di-O-trityl-2'-deoxyuridine
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With formic acid at 0℃; for 0.0166667h; | 40% |
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
5'-O-hexanoyl-2'-deoxy-5-trifluoromethyluridine
B
2'-deoxy-5-trifluoromethyluridine
Conditions | Yield |
---|---|
With phosphate buffer In N,N-dimethyl-formamide at 25℃; for 18h; enzym: Pseudomonas fluorescens; | A 62 % Chromat. B 6 % Chromat. |
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
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. |
Hazard Codes: Xn,Xi
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 , 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 .