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54-20-6

Basic Information
CAS No.: 54-20-6
Name: Trifluorothymine
Article Data: 34
Molecular Structure:
Molecular Structure of 54-20-6 (Trifluorothymine)
Formula: C5H3F3N2O2
Molecular Weight: 180.086
Synonyms: Uracil,5-(trifluoromethyl)- (7CI,8CI);5-(Trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;5-(Trifluoromethyl)uracil;5-Trifluoromethyl-1H-pyrimidine-2,4-dione;NSC73757;
EINECS: 200-197-5
Density: 1.554 g/cm3
Melting Point: 245-246 °C(lit.)
Boiling Point: 350oC
Solubility: insoluble in water
Appearance: white to faintly yellow crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 22-36/38-40-36/37/38
Safety: 24/25-36-26
PSA: 65.72000
LogP: 0.08200
Synthetic route
2314-97-8

iodotrifluoromethane

66-22-8

uracil

54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With iron(III) sulfate; dihydrogen peroxide In water; dimethyl sulfoxide at 40 - 50℃; for 0.333333h; Product distribution / selectivity;93%
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide In water at 40 - 50℃; for 0.333333h; Product distribution / selectivity;87%
With caesium carbonate In dimethyl sulfoxide for 12h; Reagent/catalyst; Solvent; Inert atmosphere; Irradiation;81%
2926-29-6

Langlois reagent

66-22-8

uracil

54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With sodium persulfate; copper(II) sulfate In water at 60 - 65℃; for 6h; Temperature; Reagent/catalyst;91.9%
With mesoporous graphitic carbon nitride In dimethyl sulfoxide at 25℃; Irradiation;84%
With di-tert-butyl peroxide; sodium sulfite In dichloromethane; water at 0 - 10℃; for 8h;71.1%
Stage #1: Langlois reagent In ethyl acetate at 40 - 50℃; for 1h;
Stage #2: uracil With FeSO4.7H2O; silica gel In water at 40 - 50℃;
Stage #3: With tert.-butylhydroperoxide In water at 40 - 70℃; Time; Reagent/catalyst; Temperature;
With tert.-butylhydroperoxide; ferrous(II) sulfate heptahydrate In water at 45 - 70℃; Reagent/catalyst; Solvent; Temperature;73 %Chromat.
153600-17-0

2,4-difluoro-5-trifluoromethyl-pyrimidine

54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With potassium fluoride at 50℃; for 5h;91%
With potassium fluoride In water
With potassium fluoride In water
3932-97-6

2,4-dichloro-5-trifluoromethylpyrimidine

54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With acetic acid In water at 110℃; for 5h;90.6%
116393-64-7

1,3-bis(benzyloxymethyl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione

54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With trifluoroacetic acid at 72℃; for 0.5h;88%
2145-56-4

5-trifluoromethyl-5,6-dihydrouracil

54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With copper(ll) bromide In acetic acid; N,N-dimethyl-formamide at 115℃; for 14h; var. temp. time and solv.: aq. DMF; constant-electrolysis with Pt electrodes with KBr;82%
With bromine 1.) AcOH, 2.) DMF, reflux; Multistep reaction;
39971-65-8

bis(((trifluoromethyl)sulfinyl)oxy)zinc

66-22-8

uracil

54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With tetraethylammonium perchlorate In dimethyl sulfoxide at 20℃; for 8h; Reagent/catalyst; Electrochemical reaction;75%
197515-85-8

cis,trans-3-dimethylamino-2-trifluoromethacryloyl fluoride

54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With sulfuric acid for 0.5h; Substitution;60%

TMG•CF3I

66-22-8

uracil

54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With dipotassium peroxodisulfate; copper(II) acetate monohydrate In acetic acid at 90℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;57%
With dipotassium peroxodisulfate; copper(II) acetate monohydrate; acetic acid at 90℃; for 24h; Inert atmosphere; Sealed tube;57%
371-76-6

bis(trifluoromethyl)mercury

66-22-8

uracil

54-20-6

5-trifluoromethyluracil

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In water for 100h; Irradiation;54%
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Chemistry

IUPAC Name: 5-(Trifluoromethyl)-1H-pyrimidine-2,4-dione 
Following is the structure of 2,4(1H,3H)-Pyrimidinedione,5-(trifluoromethyl)- (CAS NO.54-20-6):
                       
Empirical Formula: C5H3F3N2O2
Molecular Weight: 180.0847 g/mol
EINECS: 200-197-5
Storage temp.: −20°C
Water Solubility: insoluble
Melting point: 242-246 °C 
Molar Refractivity: 29.79 cm3
Molar Volume: 115.8 cm3
Density: 1.554 g/cm3
Index of Refraction: 1.427
Surface Tension: 31.7 dyne/cm
Appearance: White to faintly yellow crystalline powder
Product Categories of 2,4(1H,3H)-Pyrimidinedione,5-(trifluoromethyl)- (CAS NO.54-20-6): Pyrimidine series; Miscellaneous; Pyrimidine; Pyrimidines
Canonical SMILES: C1=C(C(=O)NC(=O)N1)C(F)(F)F
InChI: InChI=1S/C5H3F3N2O2/c6-5(7,8)2-1-9-4(12)10-3(2)11/h1H,(H2,9,10,11,12)
InChIKey: LMNPKIOZMGYQIU-UHFFFAOYSA-N

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 800mg/kg (800mg/kg)   Cancer Research. Vol. 24, Pg. 1979, 1964.
 2,4(1H,3H)-Pyrimidinedione,5-(trifluoromethyl)- (CAS NO.54-20-6) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. You can see actual entry in RTECS for complete information.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 22-36/38-40-36/37/38 
R22:Harmful if swallowed. 
R36/38:Irritating to eyes and skin. 
R40:Limited evidence of a carcinogenic effect. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26 
S24/25:Avoid contact with skin and eyes. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: YR1750000
Hazard Note: Irritant

Specification

 2,4(1H,3H)-Pyrimidinedione,5-(trifluoromethyl)- , its cas register number is 54-20-6. It also can be called 5-Trifluoromethyluracil ; Trifluorothymine ; and 5-(Trifluoromethyl)uracil; Trifluoromethyluracil .
 2,4(1H,3H)-Pyrimidinedione,5-(trifluoromethyl)- (CAS NO.54-20-6) is stable. And it should avoid the condition like incompatible materials. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide, hydrogen fluoride gas. However, its hazardous polymerization will not occur. In addition, It should be stored in a tightly closed container, or stored in a cool, dry, well-ventilated area away from incompatible substances.
The first aid measures of  2,4(1H,3H)-Pyrimidinedione,5-(trifluoromethyl)- (CAS NO.54-20-6). Such as: When on the skin: Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.