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, |
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
7. Synthesis Route
611-08-5Total: 14 Synthesis Route
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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