Trifluorothymine supplier

Name
Trifluorothymine
EINECS 200-197-5
CAS No. 54-20-6
Article Data34
CAS DataBase
Density 1.554 g/cm³
Solubility insoluble in water
Melting Point 245-246 °C(lit.)
Formula C₅H₃F₃N₂O₂
Boiling Point 350oC
Molecular Weight 180.086
Flash Point
Transport Information
Appearance white to faintly yellow crystalline powder
Safety 24/25-36-26
Risk Codes 22-36/38-40-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Uracil,5-(trifluoromethyl)- (7CI,8CI);5-(Trifluoromethyl)-2,4(1H,3H)-pyrimidinedione;5-(Trifluoromethyl)uracil;5-Trifluoromethyl-1H-pyrimidine-2,4-dione;NSC73757;
PSA 65.72000
LogP 0.08200

Synthetic route

: 2314-97-8
iodotrifluoromethane

: 66-22-8
uracil

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With trifluoroacetic acid at 72℃; for 0.5h;	88%

: 2145-56-4
5-trifluoromethyl-5,6-dihydrouracil

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
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

Conditions	Yield
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

: 57-13-6
urea

: 54-20-6
5-trifluoromethyluracil

Conditions

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

: TMG•CF3I

: 66-22-8
uracil

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
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

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

: N-(3,3,3-trifluoro-2-trifluoromethylprop-1-enyl)urea

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
With water In 1,4-dioxane at 130℃; for 0.5h; Cyclization; polytetrafluoroethylene vessel placed in autoclave with NaHCO3;	46%

: 2145-56-4
5-trifluoromethyl-5,6-dihydrouracil

A: 707-04-0
5-bromo-5-trifluoromethyl-5,6-dihydrouracil

B: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
With potassium bromide In water; N,N-dimethyl-formamide constant-current electrolysis with Pt electrodes; var. reag.: CuBr2;	A 43% B 9%

: 2923-18-4
sodium 2,2,2-trifluoroacetate

: 66-22-8
uracil

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
With potassium fluoride; dipotassium peroxodisulfate In water; N,N-dimethyl-formamide at 20℃; for 48h; Irradiation;	42%

: 66-22-8
uracil

: 407-25-0
trifluoroacetic anhydride

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) for 100h; Irradiation;	5%

: 75-63-8
Bromotrifluoromethane

: 66-22-8
uracil

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
In acetonitrile for 3h; Irradiation;

: 7057-43-4
5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
With water In 1,1,2-Trichloro-1,2,2-trifluoroethane for 1h; Heating; Yield given;

: 1780-31-0
2,6-dichloro-5-methylpyrimidine

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / Cl2 / 35 h / Heating; Irradiation 2: 90 percent / HF / 4 h / 142 °C / 7500.6 Torr 3: 91 percent / aq. KF / 5 h / 50 °C View Scheme

: 65-71-4
thymin

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / POCl3, dimethylaniline / 1.) 25 deg C, 5 min, 2.) reflux, 20 h 2: 92 percent / Cl2 / 35 h / Heating; Irradiation 3: 90 percent / HF / 4 h / 142 °C / 7500.6 Torr 4: 91 percent / aq. KF / 5 h / 50 °C View Scheme

: 153600-16-9
2,4-Dichloro-5-trichloromethylpyrimidine

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / HF / 4 h / 142 °C / 7500.6 Torr 2: 91 percent / aq. KF / 5 h / 50 °C View Scheme

aqueous sodium sulfite: aqueous sodium sulfite

: 2145-56-4
5-trifluoromethyl-5,6-dihydrouracil

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
With sulfuric acid; iodine In water; dimethyl sulfoxide	21.9 g (88%)
With sulfuric acid; iodine In water; dimethyl sulfoxide
With sulfuric acid; iodine In water; dimethyl sulfoxide
With sulfuric acid; iodine In N-methyl-acetamide; water; dimethyl sulfoxide	7.2 g (73%)

: 66-22-8
uracil

: 54-20-6
5-trifluoromethyluracil

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; iron In water; dimethyl sulfoxide at 40 - 50℃; for 0.333333h; Product distribution / selectivity;	32 %Spectr.

: 54-20-6
5-trifluoromethyluracil

: 105480-41-9
5-hydroxy-5-(trifluoromethyl)imidazolidine-2,4-dione

Conditions

Conditions	Yield
With oxygen; ozone In acetic acid at 20℃; for 2.25h; Product distribution;	98%
With oxygen; ozone In acetic acid at 20℃; for 2.25h;	98%

: 95-55-6
2-amino-phenol

: 54-20-6
5-trifluoromethyluracil

: 1276122-59-8
5-(benzo[d]oxazol-2-yl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With sodium hydroxide In water at 80℃; for 2h;	98%

: 54-20-6
5-trifluoromethyluracil

: 3932-97-6
2,4-dichloro-5-trifluoromethylpyrimidine

Conditions

Conditions	Yield
With phosphoric acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate at 85 - 100℃; for 20h;	95%
With phosphoric acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate In water at 85 - 100℃; for 20.25h;	95%
With N-ethyl-N,N-diisopropylamine; trichlorophosphate; phosphoric acid at 85 - 100℃; for 20.25h;	95%

: 75-77-4
chloro-trimethyl-silane

: 1450-14-2
1,1,1,2,2,2-hexamethyldisilane

: 54-20-6
5-trifluoromethyluracil

: 7057-43-4
5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine

Conditions

Conditions	Yield
at 125℃; for 24h;	94.4%

...Expand

: 24424-99-5
di-tert-butyl dicarbonate

: 54-20-6
5-trifluoromethyluracil

: 2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap In acetonitrile at 20℃; for 4h;	93%

: 75-77-4
chloro-trimethyl-silane

: 54-20-6
5-trifluoromethyluracil

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 7057-43-4
5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine

Conditions

Conditions	Yield
at 20 - 125℃; for 2h;	92.5%

...Expand

: 74-85-1
ethene

: 54-20-6
5-trifluoromethyluracil

: 6-trifluoromethyl-2,4-diaza-bicyclo[4.2.0]octane-3,5-dione

Conditions

Conditions	Yield
In acetone at 20℃; Irradiation;	91%

: 54-20-6
5-trifluoromethyluracil

: 108646-05-5
(3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

: 1293285-26-3
1-(2,3,4-tri-O-acetyl-α-D-arabinopyranosyl)-5-(trifluoromethyl)uracil

Conditions

Conditions	Yield
Stage #1: 5-trifluoromethyluracil With 1,1,1,3,3,3-hexamethyl-disilazane; saccharin In acetonitrile for 0.5h; Inert atmosphere; Reflux; Stage #2: (3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 1h; Inert atmosphere; Reflux;	88%

: 1068-57-1
acetic acid hydrazide

: 54-20-6
5-trifluoromethyluracil

: 1276122-47-4
5-(5-methyl-1,3,4-oxadiazol-2-yl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With sodium hydroxide In water at 80℃; for 48h;	88%

: 288-88-0
1,2,4-Triazole

: 54-20-6
5-trifluoromethyluracil

: 1622314-97-9
2,4-bis[1,2,4]triazol-1-yl-5-trifluoromethylpyrimidine

Conditions

Conditions	Yield
Stage #1: 1,2,4-Triazole With triethylamine; trichlorophosphate In dichloromethane at 0 - 5℃; for 4.5h; Large scale; Stage #2: 5-trifluoromethyluracil In dichloromethane at 0 - 25℃; for 16.5h; Large scale;	87%

: 54-20-6
5-trifluoromethyluracil

: 201287-82-3
1,2-di-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyle

: 362607-77-0
1-(3,5-di-O-benzoyl-β-L-xylo-furanosyl)-5-(trifluoromethyl)uracil

Conditions

Conditions	Yield
Stage #1: 5-trifluoromethyluracil With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 18h; Heating; Stage #2: 1,2-di-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyle With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Stage #3: With hydrazine hydrate In pyridine; acetic acid at 20℃; for 15h;	82%

: 1021426-42-5
1-(4-{4-amino-3-methoxyphenyl}piperazine-1-yl)ethan-1-one

: 54-20-6
5-trifluoromethyluracil

: 2-[[4-(4-acetyl-1-piperazinyl)-2-methoxyphenyl]amino]-5-(trifluoromethyl)pyrimidin-4-one

Conditions

Conditions	Yield
Stage #1: 5-trifluoromethyluracil With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 60℃; for 24h; Inert atmosphere; Stage #2: 1-(4-{4-amino-3-methoxyphenyl}piperazine-1-yl)ethan-1-one With sodium hydride In tetrahydrofuran at 70℃; for 5h; Reagent/catalyst;	82%

: 118493-85-9, 117771-39-8, 1141922-26-0
acetamide oxime

: 54-20-6
5-trifluoromethyluracil

: 1138450-62-0
5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With sodium hydroxide In water at 80℃; for 48h;	80%

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 54-20-6
5-trifluoromethyluracil

: 199444-41-2
5-trifluoromethyl-1-(2-trimethylsilyl)ethoxymethyl-pyrimidine-2,4-dione

Conditions

Conditions	Yield
	76%
With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane 1.) reflux, 15 h; 2.) 0 - 5 deg C, then room temp., 1 h; Yield given. Multistep reaction;

: 54-20-6
5-trifluoromethyluracil

: 169566-58-9
ethyl 2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-2-chloroacetamido)acetate

: ethyl-2-(N-(2-((tert-butoxycarbonyl)amino)-ethyl)-2-(2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	76%

: 5292-43-3
bromoacetic acid tert-butyl ester

: 54-20-6
5-trifluoromethyluracil

: 1434143-39-1
tert-butyl [5-(trifluoromethyl)uracil-N1-yl]acetate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	74%

: 1191-99-7
2,3-dihydro-2H-furan

: 75-78-5
dimethylsilicon dichloride

: 54-20-6
5-trifluoromethyluracil

: 25509-03-9
1-(tetrahydrofuran-2-yl)-5-trifluoromethylpyrimidine-2,4-dione

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane	72%

...Expand

: 1222988-00-2
4-(benzyloxy)-3-[(benzyloxy)methyl]-3-fluorobutylbromide

: 54-20-6
5-trifluoromethyluracil

: 1222988-06-8
1-[4-(benzyloxy)-3-[(benzyloxy)methyl]-3-fluorobutyl]-5-trifluoromethyluracil

Conditions

Conditions	Yield
With lithium carbonate; caesium carbonate In N,N-dimethyl-formamide at 90℃; for 1h;	72%

: 100-39-0
benzyl bromide

: 54-20-6
5-trifluoromethyluracil

: 98406-57-6
1-benzyl-5-trifluoromethyluracil

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃;	70%

: 6926-58-5
4,4-dimethylthiosemicarbazide

: 54-20-6
5-trifluoromethyluracil

: 1276122-46-3
5-(5-(dimethylamino)-1,3,4-thiadiazol-2-yl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With sodium hydroxide In water at 80℃; for 48h;	69%

: 54-20-6
5-trifluoromethyluracil

: 194474-73-2
2′,3′,5′-tri-O-acetyl-5-nitrouridine

: 65499-41-4
(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate

Conditions

Conditions	Yield
Stage #1: 5-trifluoromethyluracil; 2′,3′,5′-tri-O-acetyl-5-nitrouridine With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20℃; for 1h; Microwave irradiation; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 80℃; for 2h; Microwave irradiation; Sealed tube;	69%

: 104249-15-2
trans-1-bromo-4-phthalimido-2-butene

: 54-20-6
5-trifluoromethyluracil

: (E)-9-[4-phthalimido-2-butenyl]-5-(trifluoromethyl)uracil

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h;	68%

Trifluorothymine Chemical Properties

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/cm³Index 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

Trifluorothymine 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.

Trifluorothymine Safety Profile

Hazard Codes: Irritant Xi
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

Trifluorothymine 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.

Product Name

Trifluorothymine

Synthetic route

Trifluorothymine Chemical Properties

Trifluorothymine Toxicity Data With Reference

Trifluorothymine Safety Profile

Trifluorothymine Specification

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