611-08-5

Basic information

• Product Name: 5-Nitrouracil
• Synonyms: 5-NITRO-2,4-DIHYDROXYPYRIMIDINE;5-NITROPYRIMIDINE-2,4(1H,3H)-DIONE;5-NITROPYRIMIDINE-2,4-DIOL;5-NITROURACIL;NITROURACIL;2,4-Dihydroxy-5-nitropyrimidin;3h)-pyrimidinedione,5-nitro-4(1h;5-Nitro-1H-pyrimidine-2,4-dione
• CAS NO: 611-08-5
• Molecular Formula: C₄H₃N₃O₄
• Molecular Weight: 157.08
• 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;marker
• Mol File: 611-08-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 281.7°C (rough estimate)
• Flash Point: 227.9 °C
• Appearance: Off-white to pale yellow/Crystalline Powder or Needles
• Density: 1.8278 (rough estimate)
• Vapor Pressure: 7.81E-09mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO, Water
• PKA: 5.19±0.10(Predicted)
• Water Solubility: 3.61g/L(25 oC)
• BRN: 10410
• CAS DataBase Reference: 5-Nitrouracil(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitrouracil(611-08-5)
• EPA Substance Registry System: 5-Nitrouracil(611-08-5)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 22-24/25-45-36/37/39-26-16
• WGK Germany: 2
• RTECS: UV9104545
• TSCA: Yes
• Hazardous Substances Data: 611-08-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 611-08-5 differently. You can refer to the following data:
1. 5-Nitrouracil is a compound useful in organic synthesis.
2. 5-Nitrouracil (cas# 611-08-5) is a compound useful in organic synthesis.

Chemical Properties

Off-White Solid

Purification Methods

The uracil recrystallises in prisms from boiling H2O as the monohydrate and loses H2O on drying in vacuo. [UV: Brown J Chem Soc 3647 1959, Brown J Appl Chem 2 239 1952, Johnson J Am Chem Soc 63 263 1941, Beilstein 24 I 313, 24 II 171, 24 III/IV 1236.]

InChI:InChI=1/C4H3N3O4/c8-3-2(7(10)11)1-5-4(9)6-3/h1H,(H2,5,6,8,9)

Synthetic route

uracil (66-22-8) → 5-nitrobarbituric acid (611-08-5)

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

benzoin oxime (441-38-3) → 5-nitrobarbituric acid (611-08-5) + benzaldehyde (100-52-7) + benzonitrile (100-47-0)

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

Benzophenone oxime (574-66-3) + 2,4-Dichloro-5-nitropyrimidine (49845-33-2) → 5-nitrobarbituric acid (611-08-5) + 2,4-bis-diphenyliminoxy-5-nitropyrimidine

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

6-Methyluracil (626-48-2) → 5-nitrobarbituric acid (611-08-5)

Conditions	Yield
With sulfuric acid; nitric acid

4-chloro-2-ethylsulfanyl-pyrimidine (98198-74-4) → 5-nitrobarbituric acid (611-08-5)

Conditions	Yield
With sulfuric acid; nitric acid

2-ethylthio-3H-pyrimidin-4-one (6965-19-1) → 5-nitrobarbituric acid (611-08-5)

Conditions	Yield
With sulfuric acid; nitric acid

5-nitroorotic acid (17687-24-0) → 5-nitrobarbituric acid (611-08-5)

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

4-hydroxy-2-mercaptopyrimidine (141-90-2) → 5-nitrobarbituric acid (611-08-5)

Conditions	Yield
With nitric acid

para-dinitrobenzene (100-25-4) + 5-nitrouracil (radical anion) (58431-12-2) → 5-nitrobarbituric acid (611-08-5) + 1,4-dinitroanthracene radical anion (100-25-4)

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

(4-nitrophenyl)ethanone (100-19-6) + 5-nitrouracil (radical anion) (58431-12-2) → 5-nitrobarbituric acid (611-08-5) + p-nitroacetophenone anion radical (100-19-6)

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

2,4-Dichloro-5-nitropyrimidine (49845-33-2) → 5-nitrobarbituric acid (611-08-5)

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

1-nitrouracil → 5-nitrobarbituric acid (611-08-5)

Conditions	Yield
at 150℃;

2-amino-5-nitropyrimidin-4(3H)-one (7254-29-7) + sulfuric acid (7664-93-9) → 5-nitrobarbituric acid (611-08-5)

Conditions	Yield
at 190 - 200℃;

4-amino-5-nitropyrimidin-2(1H)-one (69099-99-6) + sulfuric acid (7664-93-9) → 5-nitrobarbituric acid (611-08-5)

Conditions	Yield
at 185 - 200℃; im Rohr;

5-nitroorotic acid (17687-24-0) + water (7732-18-5) → 5-nitrobarbituric acid (611-08-5)

2-thiouracil (141-90-2) + nitric acid (7697-37-2) → 5-nitrobarbituric acid (611-08-5)

5-nitro-uracil-carboxylic acid-(4) → 5-nitrobarbituric acid (611-08-5)

Conditions	Yield
at 150℃;
With water

acidic potassium salt of/the/ 5-nitro-uracil-carboxylic acid-(4) → 5-nitrobarbituric acid (611-08-5)

Conditions	Yield
at 130 - 170℃;

anhydronitrouridinecarboxylic acid → 5-nitrobarbituric acid (611-08-5)

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

6-Methyluracil (626-48-2) + HNO3+H2SO4 → 5-nitrobarbituric acid (611-08-5)

4-chloro-2-ethylsulfanyl-pyrimidine (98198-74-4) + HNO3+H2SO4 → 5-nitrobarbituric acid (611-08-5)

2-ethylthio-3H-pyrimidin-4-one (6965-19-1) + HNO3+H2SO4 → 5-nitrobarbituric acid (611-08-5)

uracil (66-22-8) + HNO3 → 5-nitrobarbituric acid (611-08-5)

1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-nitropyrimidine-2,4(1H,3H)-dione (3106-01-2) → 5-nitrobarbituric acid (611-08-5) + 2-deoxy–α-D-ribose 1-phosphate (17039-17-7)

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

5-nitrobarbituric acid (611-08-5) + methyl bromide (74-83-9) → 1,3-dimethyl-5-nitrouracil (41613-26-7)

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

5-nitrobarbituric acid (611-08-5) + 1,8-diazabicyclo[5.4.0]undec-7-ene (6674-22-2) → 5-nitro-1H-pyrimidine-2,4-dione; compound with 2,3,4,6,7,8,9,10-octahydro-pyrimido[1,2-a]azepine

Conditions	Yield
In acetonitrile at 20℃;	97%

5-nitrobarbituric acid (611-08-5) + 8-amino quinoline (578-66-5) + copper(II) acetate monohydrate (6046-93-1) → C13H10CuN5O4(1+)

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%

5-nitrobarbituric acid (611-08-5) → 2,4-Dichloro-5-nitropyrimidine (49845-33-2)

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%

glycidyl methyl ether (930-37-0) + 5-nitrobarbituric acid (611-08-5) → 1-(2-hydroxy-3-methoxypropyl)-5-nitrouracil

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

5-nitrobarbituric acid (611-08-5) + Bromodiphenylmethane (776-74-9) → 1-benzhydryl-5-nitropyrimidine-2,4(1H,3H)-dione

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%

pyridine (110-86-1) + 5-nitrobarbituric acid (611-08-5) + trimethyl phosphite (512-56-1) → C6H8N(1+)*C4H3N3O4*C2H6O4P(1-) (126118-81-8)

Conditions	Yield
for 5h; Heating;	82%

5-nitrobarbituric acid (611-08-5) + Phenyl glycidyl ether (122-60-1) → 1-(2-hydroxy-3-phenoxypropyl)pyrimidine-5-nitro-2,4(1H,3H)-dione + 1,3-bis(2-hydroxy-3-phenoxypropyl)pyrimidine-5-nitro-2,4(1H,3H)-dione

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

5-nitrobarbituric acid (611-08-5) + 3-(4-chlorophenoxy)-1-propanol (18673-04-6) → 1-(3-(4-chlorophenoxy) propyl)-5-nitropyrimidine-2,4 (1H, 3H)-dione (1198085-46-9)

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%

5-nitrobarbituric acid (611-08-5) → 5-Aminouracil (932-52-5)

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

5-nitrobarbituric acid (611-08-5) + butan-1-ol (71-36-3) → 1-butyl-5-nitropyrimidine-2,4(1H,3H)-dione (28485-13-4)

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%

5-nitrobarbituric acid (611-08-5) + methyl iodide (74-88-4) → 1,3-dimethyl-5-nitrouracil (41613-26-7)

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;

5-nitrobarbituric acid (611-08-5) + methyl iodide (74-88-4) → 1-methyl-5-nitrouracil (28495-88-7) + 1,3-dimethyl-5-nitrouracil (41613-26-7) + 3-methyl-5-nitro-2,4(1H,3H)pyrimidinedione (25912-37-2)

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

5-nitrobarbituric acid (611-08-5) + ethyl acrylate (140-88-5) → 3-(5-nitro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid ethyl ester (2950-88-1)

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

5-nitrobarbituric acid (611-08-5) + methyl iodide (74-88-4) → 1-methyl-5-nitrouracil (28495-88-7)

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%

5-nitrobarbituric acid (611-08-5) + acrylic acid n-butyl ester (141-32-2) → 3-(5-nitro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid butyl ester (1370413-79-8)

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

5-nitrobarbituric acid (611-08-5) + Thiotepa (52-24-4) → N,N',N''-Tris<β-(5-nitro-3-uracil)ethyl>thiophosphoric acid triamide (84295-07-8)

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

5-nitrobarbituric acid (611-08-5) + acrylic acid methyl ester (292638-85-8) → 3-(3,4-dihydro-5-nitro-2,4-dioxo-(2H)pyrimidin-1-yl)propanoic acid methyl ester (918968-22-6)

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;

5-nitrobarbituric acid (611-08-5) + trimethyl phosphite (512-56-1) → 1-methyl-5-nitrouracil (28495-88-7)

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

5-nitrobarbituric acid (611-08-5) + 8-amino quinoline (578-66-5) + copper(II) acetate monohydrate (6046-93-1) → C13H10N5NiO4(1+)

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%

5-nitrobarbituric acid (611-08-5) + sodium diphenyl phosphate (3279-55-8) → C12H10O4P(1-)*C4H3N3O4*Na(1+) (126118-86-3)

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

5-nitrobarbituric acid (611-08-5) + 1,1,1-trifluoro-2-bromo-2-chloroethane (151-67-7) → C10H4BrClN6O8

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

piperidine (110-89-4) + 5-nitrobarbituric acid (611-08-5) → 5-nitro-2,4-di(piperidin-1-yl)pyrimidine

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

5-nitrobarbituric acid (611-08-5) + phosphorisocyanatidic acid dimethyl ester (867-04-9) → [3-(Dimethoxy-phosphorylaminocarbonyl)-5-nitro-2,6-dioxo-3,6-dihydro-2H-pyrimidine-1-carbonyl]-phosphoramidic acid dimethyl ester

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

piperidine (110-89-4) + 5-nitrobarbituric acid (611-08-5) + formaldehyd (50-00-0) → N-3-Piperidinomethylene-5-nitrouracil (75682-16-5)

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

morpholine (110-91-8) + 5-nitrobarbituric acid (611-08-5) + formaldehyd (50-00-0) → N-3-Morpholinomethylene-5-nitrouracil (75682-15-4)

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

5-nitrobarbituric acid (611-08-5) + 1,5-dibromo-pentane (111-24-0) → 1,3-bis(5-bromopentyl)-5-nitro-1,2,3,4-tetrahydropyrimidine-2,4-dione (1131732-36-9)

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%

Upstream product

• 626-48-2 6-Methyluracil 
• 6965-19-1 2-ethylthio-3H-pyrimidin-4-one 
• 17687-24-0 5-nitroorotic acid 
• 141-90-2 4-hydroxy-2-mercaptopyrimidine 
• 7254-29-7 2-amino-5-nitropyrimidin-4(3H)-one 
• 7664-93-9 sulfuric acid 
• 69099-99-6 4-amino-5-nitropyrimidin-2(1H)-one 
• 7732-18-5 water 
• 141-90-2 2-thiouracil 
• 7697-37-2 nitric acid 
• 98198-74-4 4-chloro-2-ethylsulfanyl-pyrimidine 
• 66-22-8 uracil 
• 66-22-8 2,4-dihydroxypyrimidine 
• 3106-01-2 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-nitropyrimidine-2,4(1H,3H)-dione 

Downstream Products

• 20636-41-3 5-hydroxyuracil 
• 932-52-5 5-Aminouracil 
• 41613-26-7 1,3-dimethyl-5-nitrouracil 
• 585-05-7 oxaluric acid 
• 5435-16-5 5-sulfaminouracil 
• 49845-33-2 2,4-Dichloro-5-nitropyrimidine 
• 2950-88-1 3-(5-nitro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid ethyl ester 
• 2950-89-2 ethyl ω-N1-[5-nitro-2,4-(1H,3H)pyrimidinedione]butanoate 
• 52522-97-1 5-nitro-2,4-bis-trimethylsilanyloxy-pyrimidine 
• 28495-88-7 1-methyl-5-nitrouracil 
• 25912-37-2 3-methyl-5-nitro-2,4(1H,3H)pyrimidinedione 
• 126118-86-3 C₁₂H₁₀O₄P^(1-)*C₄H₃N₃O₄*Na⁽¹⁺⁾ 
• 81797-05-9 5-nitroacyclouridine 
• 1080433-46-0 1-(2,6-difluoro-benzyl)-5-nitro-1H-pyrimidine-2,4-dione 

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