5-Nitrouracil supplier | CasNO.611-08-5

Name
5-Nitrouracil
EINECS 210-250-4
CAS No. 611-08-5
Article Data26
CAS DataBase
Density 1.7 g/cm³
Solubility 3.61g/L(25 oC)
Melting Point >300 °C(lit.)
Formula C₄H₃N₃O₄
Boiling Point 453.3 °C at 760 mmHg
Molecular Weight 157.086
Flash Point 227.9 °C
Transport Information
Appearance Off-white solid
Safety 22-24/25-45-36/37/39-26-16
Risk Codes 11-34
Molecular Structure
Hazard Symbols C, F
Synonyms Uracil,5-nitro- (6CI,8CI);5-Nitro-2,4-dihydroxypyrimidine;2,4(1H,3H)-Pyrimidinedione,5-nitro-;
PSA 111.54000
LogP -0.50540

Synthetic route

: 66-22-8
uracil

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 50 - 55℃; for 3h; Inert atmosphere;	92%
With sulfuric acid; nitric acid at 125℃;
With nitric acid

: 441-38-3
benzoin oxime

A: 611-08-5
5-nitrobarbituric acid

B: 100-52-7
benzaldehyde

C: 100-47-0
benzonitrile

Conditions

Conditions	Yield
With triethylamine; 2,4-Dichloro-5-nitropyrimidine In acetonitrile for 5h; Product distribution; Heating;	A n/a B 65% C 50%

...Expand

: 574-66-3
Benzophenone oxime

: 49845-33-2
2,4-Dichloro-5-nitropyrimidine

A: 611-08-5
5-nitrobarbituric acid

B: 2,4-bis-diphenyliminoxy-5-nitropyrimidine

Conditions

Conditions	Yield
In dichloromethane for 0.5h; Product distribution; Ambient temperature; other solvent, temperature, reaction time;	A 42% B 44%

...Expand

: 626-48-2
6-Methyluracil

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
With sulfuric acid; nitric acid

: 98198-74-4
4-chloro-2-ethylsulfanyl-pyrimidine

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
With sulfuric acid; nitric acid

: 6965-19-1
2-ethylthio-3H-pyrimidin-4-one

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
With sulfuric acid; nitric acid

: 17687-24-0
5-nitroorotic acid

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
at 100 - 150℃;
at 130℃; das saure Kaliumsalz reagiert;

: 141-90-2
4-hydroxy-2-mercaptopyrimidine

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
With nitric acid

: 100-25-4
para-dinitrobenzene

: 58431-12-2
5-nitrouracil (radical anion)

A: 611-08-5
5-nitrobarbituric acid

B: 100-25-4
1,4-dinitroanthracene radical anion

Conditions

Conditions	Yield
In water; isopropyl alcohol Rate constant; Thermodynamic data; Irradiation; electron transfer reaction ΔE exc.;

...Expand

: 100-19-6
(4-nitrophenyl)ethanone

: 58431-12-2
5-nitrouracil (radical anion)

A: 611-08-5
5-nitrobarbituric acid

B: 100-19-6
p-nitroacetophenone anion radical

Conditions

Conditions	Yield
In water; isopropyl alcohol Rate constant; Thermodynamic data; Irradiation; electron transfer reaction ΔE exc.;

...Expand

: 49845-33-2
2,4-Dichloro-5-nitropyrimidine

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
With benzoic acid In acetonitrile for 0.166667h; Product distribution; Ambient temperature; other reagents, reaction time, temperature, solvent;

: 1-nitrouracil

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
at 150℃;

: 7254-29-7
2-amino-5-nitropyrimidin-4(3H)-one

: 7664-93-9
sulfuric acid

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
at 190 - 200℃;

: 69099-99-6
4-amino-5-nitropyrimidin-2(1H)-one

: 7664-93-9
sulfuric acid

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
at 185 - 200℃; im Rohr;

: 17687-24-0
5-nitroorotic acid

: 7732-18-5
water

: 611-08-5
5-nitrobarbituric acid

: 141-90-2
2-thiouracil

: 7697-37-2
nitric acid

: 611-08-5
5-nitrobarbituric acid

5-nitro-uracil-carboxylic acid-(4): 5-nitro-uracil-carboxylic acid-(4)

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
at 150℃;
With water

acidic potassium salt of/the/ 5-nitro-uracil-carboxylic acid-(4): acidic potassium salt of/the/ 5-nitro-uracil-carboxylic acid-(4)

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
at 130 - 170℃;

anhydronitrouridinecarboxylic acid: anhydronitrouridinecarboxylic acid

: 611-08-5
5-nitrobarbituric acid

Conditions

Conditions	Yield
With sulfuric acid at 130 - 135℃; im Rohr;

: 626-48-2
6-Methyluracil

HNO3+H2SO4: HNO3+H2SO4

: 611-08-5
5-nitrobarbituric acid

: 98198-74-4
4-chloro-2-ethylsulfanyl-pyrimidine

HNO3+H2SO4: HNO3+H2SO4

: 611-08-5
5-nitrobarbituric acid

: 6965-19-1
2-ethylthio-3H-pyrimidin-4-one

HNO3+H2SO4: HNO3+H2SO4

: 611-08-5
5-nitrobarbituric acid

: 66-22-8
uracil

HNO3: HNO3

: 611-08-5
5-nitrobarbituric acid

: 3106-01-2
1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-nitropyrimidine-2,4(1H,3H)-dione

A: 611-08-5
5-nitrobarbituric acid

B: 17039-17-7
2-deoxy–α-D-ribose 1-phosphate

Conditions

Conditions	Yield
With thymidine phosphorylase; 5-fluoro-6-[(2-aminoimidazol-1-yl)methyl]uracil; hydrogenphosphate Kinetics; Concentration; Reagent/catalyst; Enzymatic reaction;

: 611-08-5
5-nitrobarbituric acid

: 74-83-9
methyl bromide

: 41613-26-7
1,3-dimethyl-5-nitrouracil

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 20℃; for 24h;	100%

: 611-08-5
5-nitrobarbituric acid

: 6674-22-2
1,8-diazabicyclo[5.4.0]undec-7-ene

: 5-nitro-1H-pyrimidine-2,4-dione; compound with 2,3,4,6,7,8,9,10-octahydro-pyrimido[1,2-a]azepine

Conditions

Conditions	Yield
In acetonitrile at 20℃;	97%

: 611-08-5
5-nitrobarbituric acid

: 578-66-5
8-amino quinoline

: 6046-93-1
copper(II) acetate monohydrate

: C13H10CuN5O4(1+)

Conditions

Conditions	Yield
Stage #1: 8-amino quinoline; copper(II) acetate monohydrate In methanol at 70℃; for 0.75h; Stage #2: 5-nitrobarbituric acid In methanol at 70℃; for 1h;	94.9%

...Expand

: 611-08-5
5-nitrobarbituric acid

: 49845-33-2
2,4-Dichloro-5-nitropyrimidine

Conditions

Conditions	Yield
With trichlorophosphate In N,N-dimethyl-aniline at 110℃; for 8h;	94%
With N,N-dimethyl-aniline; trichlorophosphate Reflux;	74%
With N-ethyl-N,N-diisopropylamine; trichlorophosphate at 0 - 25℃;	70%

: 930-37-0
glycidyl methyl ether

: 611-08-5
5-nitrobarbituric acid

: 1-(2-hydroxy-3-methoxypropyl)-5-nitrouracil

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Heating;	89%

: 611-08-5
5-nitrobarbituric acid

: 776-74-9
Bromodiphenylmethane

: 1-benzhydryl-5-nitropyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; iodine In acetonitrile for 3.5h; Reflux;	84.5%
With N,O-bis-(trimethylsilyl)-acetamide; iodine In acetonitrile at 20℃; for 24h;	77%
Stage #1: 5-nitrobarbituric acid With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20℃; Stage #2: Bromodiphenylmethane With iodine In acetonitrile Heating;	72%

: 110-86-1
pyridine

: 611-08-5
5-nitrobarbituric acid

: 512-56-1
trimethyl phosphite

: 126118-81-8
C6H8N(1+)*C4H3N3O4*C2H6O4P(1-)

Conditions

Conditions	Yield
for 5h; Heating;	82%

...Expand

: 611-08-5
5-nitrobarbituric acid

: 122-60-1
Phenyl glycidyl ether

A: 1-(2-hydroxy-3-phenoxypropyl)pyrimidine-5-nitro-2,4(1H,3H)-dione

B: 1,3-bis(2-hydroxy-3-phenoxypropyl)pyrimidine-5-nitro-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With tetrabutylammomium bromide; magnesium oxide at 170℃; for 0.0166667h; microwave irradiation;	A 82% B 15%

...Expand

: 611-08-5
5-nitrobarbituric acid

: 18673-04-6
3-(4-chlorophenoxy)-1-propanol

: 1198085-46-9
1-(3-(4-chlorophenoxy) propyl)-5-nitropyrimidine-2,4 (1H, 3H)-dione

Conditions

Conditions	Yield
With iodine; potassium carbonate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide for 10h; Reflux; regioselective reaction;	82%
With potassium carbonate; 1-n-butyl-3-methylimidazolim bromide; triethylamine; p-toluenesulfonyl chloride at 80℃; for 11h; Green chemistry;	71%
With tetrachloromethane; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide for 10h; Reflux;	68%

: 611-08-5
5-nitrobarbituric acid

: 932-52-5
5-Aminouracil

Conditions

Conditions	Yield
With ammonia at 75℃; for 3h; pH=8; Inert atmosphere;	81%
With aluminium amalgam; ammonia
With hydrogenchloride; tin

: 611-08-5
5-nitrobarbituric acid

: 71-36-3
butan-1-ol

: 28485-13-4
1-butyl-5-nitropyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With tetrachloromethane; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide for 10h; Reflux;	81%
With potassium carbonate; triethylamine In N,N-dimethyl-formamide for 10h; Heating;	76%

: 611-08-5
5-nitrobarbituric acid

: 74-88-4
methyl iodide

: 41613-26-7
1,3-dimethyl-5-nitrouracil

Conditions

Conditions	Yield
Stage #1: 5-nitrobarbituric acid With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 25℃; for 20h;	81%
With sodium hydride In N,N-dimethyl-formamide for 4h; Cooling with ice; Inert atmosphere;
Stage #1: 5-nitrobarbituric acid With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 20h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere;

: 611-08-5
5-nitrobarbituric acid

: 74-88-4
methyl iodide

A: 28495-88-7
1-methyl-5-nitrouracil

B: 41613-26-7
1,3-dimethyl-5-nitrouracil

C: 25912-37-2
3-methyl-5-nitro-2,4(1H,3H)pyrimidinedione

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide In methanol; acetonitrile at 40℃; for 72h;	A 80% B n/a C n/a

...Expand

: 611-08-5
5-nitrobarbituric acid

: 140-88-5
ethyl acrylate

: 2950-88-1
3-(5-nitro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid ethyl ester

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 60℃; Aza-Micheal reaction;	79%

: 611-08-5
5-nitrobarbituric acid

: 74-88-4
methyl iodide

: 28495-88-7
1-methyl-5-nitrouracil

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide	77%
With sodium hydroxide; potassium carbonate In N-methyl-acetamide; water	77%
With sodium hydroxide; potassium carbonate In N-methyl-acetamide; water	77%

: 611-08-5
5-nitrobarbituric acid

: 141-32-2
acrylic acid n-butyl ester

: 1370413-79-8
3-(5-nitro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid butyl ester

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 60℃; Aza-Micheal reaction;	75%

: 611-08-5
5-nitrobarbituric acid

: 52-24-4
Thiotepa

: 84295-07-8
N,N',N''-Tris<β-(5-nitro-3-uracil)ethyl>thiophosphoric acid triamide

Conditions

Conditions	Yield
In water at 37℃; for 288h;	74.2%

: 611-08-5
5-nitrobarbituric acid

: 292638-85-8
acrylic acid methyl ester

: 918968-22-6
3-(3,4-dihydro-5-nitro-2,4-dioxo-(2H)pyrimidin-1-yl)propanoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 60℃; Aza-Micheal reaction;	71%
In N,N-dimethyl-formamide at 20℃; Michael-type addition; regioselective reaction;	54%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Michael condensation;

: 611-08-5
5-nitrobarbituric acid

: 512-56-1
trimethyl phosphite

: 28495-88-7
1-methyl-5-nitrouracil

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 5h; Heating;	70%

: 611-08-5
5-nitrobarbituric acid

: 578-66-5
8-amino quinoline

: 6046-93-1
copper(II) acetate monohydrate

: C13H10N5NiO4(1+)

Conditions

Conditions	Yield
Stage #1: 8-amino quinoline; copper(II) acetate monohydrate In methanol at 70℃; for 0.75h; Stage #2: 5-nitrobarbituric acid In methanol at 70℃; for 1h;	68.2%

...Expand

: 611-08-5
5-nitrobarbituric acid

: 3279-55-8
sodium diphenyl phosphate

: 126118-86-3
C12H10O4P(1-)*C4H3N3O4*Na(1+)

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Heating;	56%

: 611-08-5
5-nitrobarbituric acid

: 151-67-7
1,1,1-trifluoro-2-bromo-2-chloroethane

: C10H4BrClN6O8

Conditions

Conditions	Yield
With potassium hydroxide; dibenzo-18-crown-6 In N,N-dimethyl-formamide; benzene at 80 - 90℃; Substitution;	53.2%

: 110-89-4
piperidine

: 611-08-5
5-nitrobarbituric acid

: 5-nitro-2,4-di(piperidin-1-yl)pyrimidine

Conditions

Conditions	Yield
With copper acetylacetonate; di-tert-butyl peroxide; N,N-dimethyl-formamide at 100℃; for 10h; Green chemistry;	53%

: 611-08-5
5-nitrobarbituric acid

: 867-04-9
phosphorisocyanatidic acid dimethyl ester

: [3-(Dimethoxy-phosphorylaminocarbonyl)-5-nitro-2,6-dioxo-3,6-dihydro-2H-pyrimidine-1-carbonyl]-phosphoramidic acid dimethyl ester

Conditions

Conditions	Yield
at 170 - 200℃; for 12h;	52.5%

: 110-89-4
piperidine

: 611-08-5
5-nitrobarbituric acid

: 50-00-0
formaldehyd

: 75682-16-5
N-3-Piperidinomethylene-5-nitrouracil

Conditions

Conditions	Yield
In methanol; water for 48h; Ambient temperature;	51.1%

...Expand

: 110-91-8
morpholine

: 611-08-5
5-nitrobarbituric acid

: 50-00-0
formaldehyd

: 75682-15-4
N-3-Morpholinomethylene-5-nitrouracil

Conditions

Conditions	Yield
In methanol; water for 48h; Ambient temperature;	45.3%

...Expand

: 611-08-5
5-nitrobarbituric acid

: 111-24-0
1,5-dibromo-pentane

: 1131732-36-9
1,3-bis(5-bromopentyl)-5-nitro-1,2,3,4-tetrahydropyrimidine-2,4-dione

Conditions

Conditions	Yield
Stage #1: 5-nitrobarbituric acid With sodium butanolate In iso-butanol for 20h; Reflux; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 50 - 60℃;	43%

5-Nitrouracil Chemical Properties

IUPAC Name: 5-Nitro-1H-pyrimidine-2,4-dione
Molecular Formula: C₄H₃N₃O₄
Molecular Weight: 157.084320 g/mol
EINECS: 210-250-4
Product Categories: Pyrimidine series; Pyridines, Pyrimidines, Purines and Pteredines; Miscellaneous; Nucleotides and Nucleosides; Pyrimidines; Functional Materials; Organic Nonlinear Optical Materials; Pyrimidine; Nucleic acids; Bases & Related Reagents; Nucleotides
Index of Refraction: 1.607
Molar Refractivity: 31.77 cm³
Molar Volume: 91.9 cm³
Surface Tension: 74.5 dyne/cm
Density: 1.7 g/cm³
Flash Point: 227.9 °C
Enthalpy of Vaporization: 74 kJ/mol
Boiling Point: 453.3 °C at 760 mmHg
Vapour Pressure: 7.81E-09 mmHg at 25 °C
Appearance: Off-White Solid
Melting Point of 5-Nitrouracil (CAS NO.611-08-5): >300 °C(lit.)

5-Nitrouracil Uses

5-Nitrouracil (CAS NO.611-08-5) is used as pharmaceutical intermediates and solvents.

5-Nitrouracil Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	3250mg/kg (3250mg/kg)		United States Patent Document. Vol. #3423508,
mouse	LD50	parenteral	1950mg/kg (1950mg/kg)		United States Patent Document. Vol. #3423508,

5-Nitrouracil Safety Profile

Hazard Codes:F ,C
Risk Statements:11-34
11:Highly Flammable
34:Causes burns
Safety Statements:22-24/25-45-36/37/39-26-16
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
16:Keep away from sources of ignition - No smoking
WGK Germany:2
RTECS:UV9104545

5-Nitrouracil Specification

5-Nitrouracil (CAS NO.611-08-5), its Synonyms are 2,4(1H,3H)-Pyrimidinedione, 5-nitro- ; Uracil, 5-nitro- .

Product Name

5-Nitrouracil

Synthetic route

5-Nitrouracil Chemical Properties

5-Nitrouracil Uses

5-Nitrouracil Toxicity Data With Reference

5-Nitrouracil Safety Profile

5-Nitrouracil Specification

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