5-bromo-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 102323
• Molecular Formular: C4H3BrN2O2
• Molecular Mass: 190.98282
• Monoisotopic Mass: 189.93778935
• SMILES: Brc1c[nH]c(=O)[nH]c1=O
• Canonical SMILES: Brc1c[nH]c(=O)[nH]c1=O
• InChI: InChI=1S/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
• InChIKey: LQLQRFGHAALLLE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-bromo-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: bromouracil
• Synonyms: 5-Bromo-2,4-dihydroxypyrimidine; 5-BROMOURACIL; 5-bromopyrimidine-2,4(1H,3H)-dione; 5-Bromouracil; 5-Bromo-2,4-(1H,3H)-pyrimidinedione; 5-溴-2,4-二羟基嘧啶; 5-溴尿嘧啶

Database IDs

• CAS Number: 51-20-7
• EC Number: 200-084-0
• MDL Number: MFCD00006017
• Beilstein Number: 127176
• Merck Index: 141440
• PubChem SID: 24851231; 24888322; 162090529
• PubChem CID: 5802
• CHEBI ID: 20552
• CHEMBL: 144730
• Chemspider ID: 5597
• Wikipedia Title: 5-Bromouracil

CALCULATED PROPERTIES

• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 7.1404057
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.03951184
• LogD (pH = 7.4): -0.4708292
• Log P: -0.029797401
• Molar Refractivity: 33.5786 cm^3
• Polarizability: 12.739561 Å^3
• Polar Surface Area: 58.2 Å^2

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Prisms
• Melting Point: ~304 °C (dec.); >300 °C(lit.); 190°C; 293 °C; ca 310°C dec.

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: YQ9060000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 68
• Safety Statements: 36/37; R
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H341
• GHS Precautionary statements: P281-P201-P202-P308+P313-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (HPLC); 98%; 98+%
• Empirical Formula (Hill Notation): C4H3BrN2O2

DETAILS

MP Biomedicals - 02101132

Crystalline

Sigma Aldrich - 852473

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 18660

Other Notes
Possesses mutagenic activity1; Incorporation into DNA2; Inhibits dihydrouracil dehydrogenase3

Toronto Research Chemicals - B688925

A major chemical mutagen. Incorporates into DNA, altering base-pair sequencing by replacing thymine.

REFERENCES

• Litman, P.M. and Pardee, A.B. Virology , 8 : 125-7, (1959).
• Skavronskaya, G., et al.: Mutat. Res., 6, 319 (1968)