5-bromo-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 149141
• Molecular Formular: C9H11BrN2O6
• Molecular Mass: 323.09744
• Monoisotopic Mass: 321.98004808
• SMILES: c1c(c(=O)[nH]c(=O)n1[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)Br
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(Br)c(=O)[nH]c1=O
• InChI: InChI=1S/C9H11BrN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1
• InChIKey: AGFIRQJZCNVMCW-UAKXSSHOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-bromo-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: BrU
• Synonyms: 5-Bromouracil-1-β-D-ribofuranoside; 5-Bromouridine; 5-BroMo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione; 5-溴尿嘧啶-1-β-D-呋喃核糖苷; 5-溴尿苷

Database IDs

• CAS Number: 957-75-5
• EC Number: 213-486-6
• MDL Number: MFCD00006528
• Beilstein Number: 33664
• PubChem SID: 162243309; 24888292
• PubChem CID: 91494

CALCULATED PROPERTIES

• Acid pKa: 7.035909
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.6020676
• LogD (pH = 7.4): -2.0986075
• Log P: -1.5897485
• Molar Refractivity: 60.1749 cm^3
• Polarizability: 23.942484 Å^3
• Polar Surface Area: 119.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 180-182 °C (dec.)(lit.); 191-193°C
• Optical Rotation: [α]22/D -11°, c = 2 in H2O

Safety Information

• RTECS: YU7300000
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C9H11BrN2O6
• Classification: Rare Derivatives of Natural Compounds

DETAILS

Sigma Aldrich - 850187

Packaging
1 g in glass bottle
250 mg in glass bottle