3D Mol Similar

5-Nitrouracil

Iupac Name：5-nitro-1H-pyrimidine-2,4-dione

CAS No.: 611-08-5

Molecular Weight：157.08432

Modify Date.: 2022-11-29 07:40

Introduction:

Off-White Solid

5-nitrouracil is a C-nitro compound consisting of uracil having a nitro group at the 5-position. It derives from a uracil.

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1. Names and Identifiers

1.1 Name: 5-Nitrouracil
1.2 Synonyms: 1,2,3,6-Tetrahydro-5-nitro-2,6-dioxopyrimidine 2,4(1H,3H)-Pyrimidinedione, 5-nitro- 2,4-Dihydroxy-5-nitropyrimidin 5-Nitro-2,4(1H,3H)-pyrimidinedione 5-NITRO-2,4-DIHYDROXYPYRIMIDINE 5-NITROPYRIMIDINE-2,4(1H,3H)-DIONE 5-NITROPYRIMIDINE-2,4-DIOL NHCONHCOC(NO 2):CH NITROURACIL NSC 9790 Uracil, 5-nitro-

1.3 CAS No.: 611-08-5

1.4 CID: 69135

1.5 EINECS(EC#): 210-250-4

1.6 Molecular Formula: C4H3N3O4 (isomer)

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

1.8 InChkey: TUARVSWVPPVUGS-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=C(C(=O)NC(=O)N1)[N+](=O)[O-]

1.10 Isomers Smiles: C1=C(C(=O)NC(=O)N1)[N+](=O)[O-]

2. Properties

2.1 Density: 1.7

2.1 Melting point: >300℃

2.1 Boiling point: 453.3 oC at 760 mmHg

2.1 Refractive index: 1.607

2.1 Flash Point: 227.9 oC

2.1 Precise Quality: 157.01200

2.1 PSA: 111.54000

2.1 logP: -0.50540

2.1 Solubility: 3.61g/L(25 ºC)

2.2 Appearance: Off-white to pale yellow Crystalline Powder or Needles

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: Off-White Solid

2.5 Color/Form: White to Yellow Solid

2.6 pKa: 5.19±0.10(Predicted)

2.7 Water Solubility: 3.61g/L(25 oC)

2.8 Stability: Stable under normal temperatures and pressures.

2.9 StorageTemp: Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

3. Use and Manufacturing

3.1 Methods of Manufacturing: Nitric acid solution (5.34 mL, 120 mmol, 70percent solution) was added drop-wise to a concentrated sulfuric acid (19.7 mL, 360 mmol, 98percent solution) during which time the temperature did not exceed 50 °C. Pyrimidine-2, 4(1H, 3H)-dione 5 (7.204 g, 60 mmol) was added in several portions to the stirred solution ensuring the temperature did not exceed 50 °C. The reaction was heated to 55 °C for 3 hours, and then cooled below room temperature and quenched with ice-water (38 mL). The resulting white precipitate was collected by filtration, washed with a small amount of ice water and dried under reduced pressure at 55 °C to yield a white solid 6 (8.658 g, 55.11 mmol, 92percent).m.p. >288 oC decomposition; Rf 0.00 (1/10, ethyl acetate/hexane); IR (ZnSe cell , solid) vmax: 3142-2811 (m, br, O-H/N-H/C-H), 1732 (s, C=O), 1677, 1624 (s, NO2), 1417 (m, C-H), 1356 (m, NO2), 1318 (s, aromatic R2NH/R3N), 1234 (s, -OH), 975, 832 (w, aromatic ring bending); 1H NMR (500 MHz, d6-DMSO): δ 8.84 (1H, s, 6-CH) ppm; 13C NMR (125 MHz, d6-DMSO): δ 155.5 (4-C=O), 149.8 (6-CH), 147.9 (2-C=O), 125.1 (5-CNO2) ppm.

3.2 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.] 5-Nitrouracil Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 Hazard Codes: C; F

4.1 Risk Statements: R11

4.1 Safety Statements: S22;S24/25

4.1 Hazard Declaration: H315

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 2

4.1 RTECS: UV9104545

4.1 Safety: 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

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

4.3 Toxicity

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,

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

ESR : X-RAY IRRAD. 15N-LABELED

1H NMR : parameter in DMSO-d6

IR : KBr disc

Mass

7. Synthesis Route

611-08-5Total: 14 Synthesis Route

66-22-8 381 Suppliers

611-08-5 189 Suppliers

Literatures:
American Chemical Journal, , vol. 33, p. 443
Yield: null

141-90-2 173 Suppliers

611-08-5 189 Suppliers

Literatures:
American Chemical Journal, , vol. 33, p. 443
Yield: null

626-48-2 206 Suppliers

611-08-5 189 Suppliers

Literatures:
Justus Liebigs Annalen der Chemie, , vol. 236, p. 50
Yield: null

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8. Precursor and Product

precursor:

7254-29-7

69099-99-6

17687-24-0

7732-18-5

49845-33-2

3106-01-2

6965-19-1

58431-12-2

98198-74-4

100-19-6

626-48-2

141-90-2

100-25-4

66-22-8

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product :

25912-37-2

106055-61-2

20636-41-3

2950-88-1

28495-88-7

2950-89-2

81797-05-9

84295-07-8

932-52-5

41613-26-7

49845-33-2

5435-16-5

9. Other Information

9.0 Storage Conditions: Nitric acid solution (5.34 mL, 120 mmol, 70percent solution) was added drop-wise to a concentrated sulfuric acid (19.7 mL, 360 mmol, 98percent solution) during which time the temperature did not exceed 50 °C. Pyrimidine-2, 4(1H, 3H)-dione 5 (7.204 g, 60 mmol) was added in several portions to the stirred solution ensuring the temperature did not exceed 50 °C. The reaction was heated to 55 °C for 3 hours, and then cooled below room temperature and quenched with ice-water (38 mL). The resulting white precipitate was collected by filtration, washed with a small amount of ice water and dried under reduced pressure at 55 °C to yield a white solid 6 (8.658 g, 55.11 mmol, 92percent).m.p. >288 oC decomposition; Rf 0.00 (1/10, ethyl acetate/hexane); IR (ZnSe cell , solid) vmax: 3142-2811 (m, br, O-H/N-H/C-H), 1732 (s, C=O), 1677, 1624 (s, NO2), 1417 (m, C-H), 1356 (m, NO2), 1318 (s, aromatic R2NH/R3N), 1234 (s, -OH), 975, 832 (w, aromatic ring bending); 1H NMR (500 MHz, d6-DMSO): δ 8.84 (1H, s, 6-CH) ppm; 13C NMR (125 MHz, d6-DMSO): δ 155.5 (4-C=O), 149.8 (6-CH), 147.9 (2-C=O), 125.1 (5-CNO2) ppm.

9.1 Mesh Entry Terms: 5-nitrouracil

9.2 Manufacturing Info: 2,4(1H,3H)-Pyrimidinedione, 5-nitro-: ACTIVE

10. Computational chemical data

Molecular Weight: 157.08432g/mol
Molecular Formula: C₄H₃N₃O₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 157.01235559
Monoisotopic Mass: 157.01235559
Complexity: 263
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 104
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcQBjOAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAHgAUAAAACAjBgAQBAALQQACJAAVWUwCAAAAAAgAgAICIAECAQAAAAAAQAAAIByIAAMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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