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

• ChemBase ID: 132388
• Molecular Formular: C9H11BrN2O5
• Molecular Mass: 307.09804
• Monoisotopic Mass: 305.98513346
• SMILES: c1c(c(=O)[nH]c(=O)n1[C@H]1C[C@@H]([C@H](O1)CO)O)Br
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cc(Br)c(=O)[nH]c1=O
• InChI: InChI=1S/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
• InChIKey: WOVKYSAHUYNSMH-RRKCRQDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-bromo-2'-deoxyuridine; 5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• Synonyms: 5-BrdU; BUdR; 5-Bromo-2′-deoxyuridine; 5-Bromo-1-(2-deoxy-β-D-ribofuranosyl)uracil; 5-Bromouracil deoxyriboside; 5-Bromo-1-(2-deoxy-beta-D-ribofuranosyl)uracil; 5-Bromo-2'-deoxyuridine; 5-BroMo-2'-deoxyuridine; Bromouridine; Radibud; Broxuridine; 5-溴-1-(2-脱氧-β-D-呋喃核糖)尿嘧啶; 5-溴脱氧尿苷; 5-溴-2′-脱氧尿苷; 5-溴-2'-脱氧尿苷

Database IDs

• CAS Number: 59-14-3
• EC Number: 200-415-9
• MDL Number: MFCD00006529
• Beilstein Number: 30395
• Merck Index: 141452
• PubChem SID: 162226665; 24850256; 24892132; 24278270; 24888474
• PubChem CID: 6035

CALCULATED PROPERTIES

• Acid pKa: 7.040325
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.70130664
• LogD (pH = 7.4): -1.1950028
• Log P: -0.68911046
• Molar Refractivity: 58.6642 cm^3
• Polarizability: 23.204786 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: NH4OH: soluble0.1 M at 20 °C, clear, colorless
• Melting Point: 191-194 °C (dec.)(lit.); ca 190°C dec.
• Optical Rotation: [α]20/D +23±1°, c = 1% in H2O; [α]22/D +23.0°, c = 1 in H2O; +31 (c=1 in 0.1N HCl)

Safety Information

• RTECS: YU7350000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 2
• Risk Statements: 46-61; 68
• Safety Statements: 36/37; 53-45
• TSCA Listed: 是
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H340-H361; H341
• GHS Precautionary statements: P201-P281-P308 + P313; P281-P201-P202-P308+P313-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Mechanism of Action: Incorporate into the DNA; Nucleoside antimetabolite

Product Information

• Purity: ≥99%; ≥99% (HPLC); ≥99.0% (HPLC); 97%; 99%
• Ignition Residue: ≤0.1%
• Impurities: ≤0.005% Phosphorus (P); ≤0.1% Insoluble matter
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.01%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.05%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• Application(s): Antineoplastic; Virucide
• Empirical Formula (Hill Notation): C9H11BrN2O5

DETAILS

Sigma Aldrich - B9285

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
用作遗传研究中诱变剂的胸苷类似物。在 S 期可选择性结合到细胞 DNA 中。
Application
5-Bromo-2′-deoxyuridine (5-BrdU) is a thymidine analogue which is incorporated into DNA. 5-BrdU is routinely and extensively used to measure DNA synthesis and to label dividing cells. Consequently 5-BrdU is used to study cell signaling and other processes that induce cell proliferation.

Sigma Aldrich - B5002

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
用作遗传研究中诱变剂的胸苷类似物。在 S 期可选择性结合到细胞 DNA 中。
包装
1, 5, 100 g in glass bottle
100, 250, 500 mg in glass bottle
Application
5-Bromo-2′-deoxyuridine (5-BrdU) is a thymidine analogue which is incorporated into DNA. 5-BrdU is routinely and extensively used to measure DNA synthesis and to label dividing cells. Consequently 5-BrdU is used to study cell signaling and other processes that induce cell proliferation.

Sigma Aldrich - 858811

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Thymidine analog used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase.
Packaging
100, 500 mg in glass bottle
5 g in glass bottle

Sigma Aldrich - 16880

Biochem/physiol Actions
Thymidine analog used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase.
Other Notes
Thymidine analogue. Inhibitor of cell differentiation : Review1; Incorporation into DNA for flow cytometric analysis2

REFERENCES

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 375A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 816C, (ir)
• Beltz, R.E. et al., J.A.C.S., 1955, 77, 736, (synth)
• Iball, J. et al., Nature (London), 1966, 209, 1230, (cryst struct)
• Hruska, F.E. et al., Can. J. Chem., 1974, 52, 497, (pmr)
• Davies, D.B., Stud. Biophys., 1976, 55, 29; CA, 85, 59065h, (cmr)
• Du Frain, R.J., Basic Life Sci., 1984, 29A, 41; 59; 83, (revs)
• Aoyama, H., Bull. Chem. Soc. Jpn., 1987, 60, 2073, (synth)
• Asakura, J. et al., J.O.C., 1990, 55, 4928, (synth, pmr, uv)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 460
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BNC750
• Thymidine analog, preferentially incorporated into cellular DNA in place of thymidine, producing increased radiosensitivity of the cell: Int. J. Radiat. Oncol. Biol. Phys., 10, 1399 (1984); 21, 709 (1991). Mutagen used in genetic research: Mutat. Res., 258, 161 (1991). Reviews on use in diagnostics and research: Histochem. J., 27, 339, 923 (1995; 28, 531 (1996).