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Home> Encyclopedia >Pharmaceutical Intermediates>Organic Intermediate>Others
6-Aminouracil structure
6-Aminouracil structure

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

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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