3D Mol Similar

6-Aminouracil

Iupac Name：6-amino-1H-pyrimidine-2,4-dione

CAS No.: 873-83-6

Molecular Weight：127.1

Modify Date.: 2022-11-29 04:39

Introduction:

Used as intermediates for pharmaceutical caffeine, theophylline, SDM, etc.

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1. Names and Identifiers

1.1 Name: 6-Aminouracil
1.2 Synonyms: 2,4(1H,3H)-Pyrimidinedione, 6-amino- 2,4-Dihydroxy-6-aminopyrimidine 2,4-Dioxo-6-imino-1,3-diaza-hexahydrobenzol 2,6-Dioxo-4-imino-hexahydropyrimidin 4(6)-AMINOURACIL 4-ADHP 4-AMINO-2,6-DIHYDROXYPYRIMIDINE 4-AMINOURACI 4-AMINOURACIL 6-amino-1,2,3,4-tetrahydro-2,4-dioxopyrimidine 6-amino-1H,3H-pyrimidine-2,4-dione 6-amino-1H-pyrimidine-2,4-dione 6-Amino-2,4(1H,3H)-pyrimidinedione 6-AMINO-2,4-DIHYDROXY-PYRIMIDINE 6-AMINO-2,4-PYRIMIDINEDIOL 6-amino-5H-pyrimidine-2,4-dione 6-AMINOPYRIMIDINE-2,4(1H,3H)-DIONE 6-aminopyrimidine-2,4-diol Aminouracil AURORA KA-377 Barbitursaeure-4-imin EINECS 212-854-3 Imino-4-uracil MFCD00006071 Pyrimidine, 2,4-dihydroxy-6-amino

1.3 CAS No.: 873-83-6

1.4 CID: 70120

1.5 EINECS(EC#): 212-854-3

1.6 Molecular Formula: C4H5N3O2 (isomer)

1.7 Inchi: InChI=1S/C4H5N3O2/c5-2-1-3(8)7-4(9)6-2/h1H,(H4,5,6,7,8,9)

1.8 InChkey: LNDZXOWGUAIUBG-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=C(NC(=O)NC1=O)N

1.10 Isomers Smiles: C1=C(NC(=O)NC1=O)N

2. Properties

2.1 Density: 1.4748 (rough estimate)

2.1 Melting point: ≥360 °C(lit.)

2.1 Boiling point: 235.85°C (rough estimate)

2.1 Refractive index: 1.5000 (estimate)

2.1 Flash Point: 580.4 oC at 760 mmHg

2.1 Precise Quality: 127.03800

2.1 PSA: 91.74000

2.1 logP: -0.77340

2.1 Appearance: Cream to light brown Crystalline Powder

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: cream to light brown crystalline powder

2.4 Color/Form: Powder

2.5 pKa: 3.76±0.10(Predicted)

2.6 Water Solubility: slightly soluble

2.7 Stability: Stable under normal temperatures and pressures.

2.8 StorageTemp: Keep in dark place,Inert atmosphere,Room temperature

3. Use and Manufacturing

3.1 Methods of Manufacturing: General procedure: Compounds 1a, 1b and 1e were prepared according to the reportedmethods26–34 by the addition of urea, methylurea and/or methylthiourea (0.1 mol) to ethyl cyanoacetate (0.1 mol) in absolute ethanol(290 mL) containing sodium (0.2 mol). The mixture was refluxed for10–12 h, allowed to cool to r.t. and acidified with acetic acid (pH 6).The resulting precipitate was washed with distilled water and dried in adesiccator overnight.1a: Yield 69percent; m.p. > 360 °C (lit. ≥ 360 °C).We have found that the microwave assisted of reaction urea (1 mmol) with cyano acetic acid (1 mmol) under solvent-free conditions results in rapid formation of the corresponding Amino uracil (Figure1).The products were easily obtained by addition of water to the reaction mixture and recrystalization of crude products from ethanol.

3.2 Purification Methods: Purify the aminouracil by dissolving it in 3M aqueous NH3, filtering hot, and adding 3M formic acid until precipitation is complete. Cool, filter off (or centrifuge), wash well with cold H2O, then EtOH and dry it in air. Dry it further in a vacuum at ~80o. [Barlin & Pfeiderer J Chem Soc (B) 1424 1971, Beilstein 25 III/IV 4107.] 6-Aminouracil Preparation Products And Raw materials Raw materials

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Signal Word: Warning

4.1 Risk Statements: S22-S24/25

4.1 Safety Statements: 22-24/25

4.1 Hazard Declaration: H302

4.1 RIDADR: NONH for all modes of transport

4.1 Safety Profile: Moderately toxic by parenteralroute. When heated to decomposition it emits toxic fumesof NOx.

4.2 Caution Statement: P264, P270, P301+P312, P330, P501

4.2 WGK Germany: 3

4.2 RTECS: YQ8750000

4.2 Report: Reported in EPA TSCA Inventory.

4.3 Safety: Safety Statements: 22-24/25?
S22:Do not breathe dust.?
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS of 6-Aminouracil (CAS NO.873-83-6): YQ8750000

4.4 Specification: ?6-Aminouracil (CAS NO.873-83-6), its Synonyms are 2,4(1H,3H)-Pyrimidinedione, 6-amino- ; 4-Amino-2,6-dihydroxylpyrimidine ; 4-Amino-2,6-dihydroxypyrimidine ; 4-Amino-2,6-dioxypyrimidine ; 4-Amino-2,6-pyrimidinediol ; 4-Aminouracil ; 6-Amino-2,4-dihydroxypyrimidine ; 6-Amino-2,4-pyrimidinediol ; Uracil, 6-amino- ; Uracil, 6-amino- (VAN) (8CI) . It is cream to light brown crystalline powder.

4.5 Toxicity: Parenteral-mouse LDL0: 2400 mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
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

13C NMR : in DMSO-d6

1H NMR : 400 MHz in DMSO-d6

IR : KBr disc

IR : nujol mull

Mass

7. Synthesis Route

873-83-6Total: 9 Synthesis Route

69-93-2 54 Suppliers

873-83-6 228 Suppliers

Literatures:
Nucleosides, Nucleotides and Nucleic Acids, , vol. 27, # 8 p. 967 - 978
Yield: null

1004-40-6 74 Suppliers

873-83-6 228 Suppliers

Literatures:
Katori; Nagano; Kunieda; Hirobe Chemical and pharmaceutical bulletin, 1981 , vol. 29, # 10 p. 3075 - 3077
Yield: ~49%

4270-27-3 150 Suppliers

873-83-6 228 Suppliers

Literatures:
Bioorganic and Medicinal Chemistry, , vol. 21, # 22 p. 6868 - 6877
Yield: null

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8. Precursor and Product

precursor:

69-93-2

79-04-9

4270-27-3

57-13-6

1004-40-6

1448-98-2

591-07-1

372-09-8

105-56-6

52386-29-5

product :

6642-31-5

21333-02-8

5442-24-0

3346-22-3

88351-89-7

30161-91-2

29817-67-2

36075-35-1

67-52-7

5971-68-6

27402-47-7

10132-07-7

39929-79-8

2434-53-9

21038-66-4

6312-73-8

79344-67-5

21236-97-5

138895-26-8

88351-90-0

View all

9. Other Information

9.0 BRN: 120491

9.1 Chemical Properties: cream to light brown crystalline powder

9.2 Safety Profile: Moderately toxic by parenteralroute. When heated to decomposition it emits toxic fumesof NOx.

9.3 Purification Methods: Purify the aminouracil by dissolving it in 3M aqueous NH3, filtering hot, and adding 3M formic acid until precipitation is complete. Cool, filter off (or centrifuge), wash well with cold H2O, then EtOH and dry it in air. Dry it further in a vacuum at ~80o. [Barlin & Pfeiderer J Chem Soc (B) 1424 1971, Beilstein 25 III/IV 4107.]

9.4 Storage Conditions: General procedure: Compounds 1a, 1b and 1e were prepared according to the reportedmethods26–34 by the addition of urea, methylurea and/or methylthiourea (0.1 mol) to ethyl cyanoacetate (0.1 mol) in absolute ethanol(290 mL) containing sodium (0.2 mol). The mixture was refluxed for10–12 h, allowed to cool to r.t. and acidified with acetic acid (pH 6).The resulting precipitate was washed with distilled water and dried in adesiccator overnight.1a: Yield 69percent; m.p. > 360 °C (lit. ≥ 360 °C).We have found that the microwave assisted of reaction urea (1 mmol) with cyano acetic acid (1 mmol) under solvent-free conditions results in rapid formation of the corresponding Amino uracil (Figure1).The products were easily obtained by addition of water to the reaction mixture and recrystalization of crude products from ethanol.

9.5 Storage features: Warehouse ventilated, low temperature and dry

9.6 Mesh Entry Terms: 6-aminouracil

9.7 Manufacturing Info: 2,4(1H,3H)-Pyrimidinedione, 6-amino-: ACTIVE

10. Computational chemical data

Molecular Weight: 127.1g/mol
Molecular Formula: C₄H₅N₃O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 127.038176411
Monoisotopic Mass: 127.038176411
Complexity: 196
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 84.2
Heavy Atom Count: 9
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: AAADcYBjMAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAHgAQAAAACACBgAABAALAAACIACFSUACAAAAAAgAAAAAAAECAAAAAAAAAAAAIFSIAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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