Uracil
- Iupac Name:1H-pyrimidine-2,4-dione
- CAS No.: 66-22-8
- Molecular Weight:112.08676
- Modify Date.: 2022-11-10 17:48
- Introduction: For biochemical research, drugs synthesis; being used as pharmaceutical intermediates, also used in organic synthesis
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1. Names and Identifiers
- 1.1 Name
- Uracil
- 1.2 Synonyms
1,2,3,4-Tetrahydropyrimidine-2,4-dione 2,4(1H,3H)-Pyrimidinedione 2,4-Pyrimidinediol 2,6-Dihydroxypyrimidine 4-Hydroxyuracil ALUMINIUM CAN WITH HANDLE AND STOPPER COATED SAFETY BOTTLE 2,5LWITHOUT CAP ISO hybarx Uracyl
- 1.3 CAS No.
- 66-22-8
- 1.4 CID
- 1174
- 1.5 EINECS(EC#)
- 200-621-9
- 1.6 Molecular Formula
- C4H4N2O2 (isomer)
- 1.7 Inchi
- InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
- 1.8 InChkey
- ISAKRJDGNUQOIC-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CNC(=O)NC1=O
- 1.10 Isomers Smiles
- C1=CNC(=O)NC1=O
2. Properties
- 2.1 Density
- 1.321 g/cm43
- 2.1 Melting point
- 335℃
- 2.1 Refractive index
- 1.501
- 2.1 Flash Point
- 220.2 °C
- 2.1 Precise Quality
- 112.02700
- 2.1 PSA
- 65.72000
- 2.1 logP
- -0.93680
- 2.1 Appearance
- fine off-white crystalline powder
- 2.2 Storage
- Ambient temperatures.
- 2.3 Chemical Properties
- Crystalline needles.Soluble in hot water, ammonium hydroxide, and other alkalies; insoluble in alcohol and ether.
- 2.4 Color/Form
- Powder
- 2.5 pKa
- 9.45(at 25℃)
- 2.6 Water Solubility
- SOLUBLE IN HOT WATER
- 2.7 Stability
- Stable. Incompatible with strong oxidizing agents.
- 2.8 StorageTemp
- Keep tightly closed. Keep away from heat, sparks, and open flame.
3. Use and Manufacturing
- 3.1 Definition
- A nitrogenous base thatis found in RNA, replacing the thymine ofDNA. It has a pyrimidine ring structure.
- 3.2 Produe Method
- It is produced through the reaction of malate, sulfuric acid and urea.
- 3.3 Purification Methods
- Uracil crystallises from water (m 339-341o) and m 338o after sublimation in high vacuum. Its solubility in H2O at 20o is 1g/300mL. [Beilstein 24 H 312, 24 I 312, 24 II 169, 24 III/IV 1193.] Uracil Preparation Products And Raw materials Preparation Products
- 3.4 Usage
- For biochemical research, drugs synthesis; being used as pharmaceutical intermediates, also used in organic synthesis
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Safety Statements
- S24/25
- 4.1 Packing Group
- I
- 4.1 Hazard Class
- 4.2
- 4.1 RIDADR
- HAZARD
- 4.1 Safety Profile
- Moderately toxic byintraperitoneal route. An experimentalteratogen. Experimental reproductiveeffects. Questionable carcinogen withexperimental tumorigenic data. Mutationdata reported. When heated todecomposition it emits toxic fumes of NOx.
- 4.2 WGK Germany
- 2
- 4.2 RTECS
- YQ8650000
- 4.2 Report
-
EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.
- 4.3 Safety
-
Moderately toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes of Uracil (CAS NO.66-22-8):?Xi
WGK Germany:?2
Safety Statements:?22-24/25?
S22: Do not breathe dust.?
S24/25: Avoid contact with skin and eyes.
- 4.4 Toxicity
-
Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
dog |
LD50 |
oral |
> 5gm/kg (5000mg/kg) |
? |
Medicamentos de Actualidad. Vol. 21, Pg. 125, 1985. |
mouse |
LD50 |
intraperitoneal |
1513mg/kg (1513mg/kg) |
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) |
Journal of Pharmacology and Experimental Therapeutics. Vol. 207, Pg. 504, 1978. |
mouse |
LD50 |
oral |
> 8gm/kg (8000mg/kg) |
? |
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 1009, 1980. |
rabbit |
LD50 |
oral |
> 10gm/kg (10000mg/kg) |
? |
Medicamentos de Actualidad. Vol. 21, Pg. 125, 1985. |
rat |
LD50 |
oral |
> 6gm/kg (6000mg/kg) |
? |
Medicamentos de Actualidad. Vol. 21, Pg. 125, 1985. |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
Pictogram(s) | No symbol. |
Signal word | No signal word. |
Hazard statement(s) | none |
Precautionary statement(s) | |
Prevention | none |
Response | none |
Storage | none |
Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
66-22-8Total: 22 Synthesis Route
-
-
|
 |
|
Literatures:
Arivett, Brock; Farone, Mary; Masiragani, Ranjith; Burden, Andrew; Judge, Shelby; Osinloye, Adedoyin; Minici, Claudia; Degano, Massimo; Robinson, Matthew; Kline, Paul
Biochimica et Biophysica Acta - Proteins and Proteomics, 2014 , vol. 1844, # 3 p. 656 - 662
Yield: null
|
-
8. Other Information
- 8.0 Usage
- Uracil is produced by hydrolysis of nucleic acid and used in biochemical research. It serves as a allosteric regulator and coenzyme for reactions in the human body and in plants. It reacts with fluorine to get 5-fluorouracil, which is an anticancer drug. Further, it is used in drug delivery and in pharmaceuticals. In addition to this, it is used in the synthesis of caffeine and in the determination of microbial contamination of tomatoes.
9. Computational chemical data
- Molecular Weight: 112.08676g/mol
- Molecular Formula: C4H4N2O2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 112.027277375
- Monoisotopic Mass: 112.027277375
- Complexity: 161
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 58.2
- Heavy Atom Count: 8
- 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: AAADcYBjMAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAHgAQAAAACADBgAQBAALAAACIACFWUACAAAAAAgAIAIAIAECAAAAAAAAAAAAIFyIAAMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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