4,5,6,7-tetrabromo-1H-1,3-benzodiazole

• ChemBase ID: 154004
• Molecular Formular: C7H2Br4N2
• Molecular Mass: 433.72018
• Monoisotopic Mass: 429.69514607
• SMILES: c1[nH]c2c(n1)c(c(c(c2Br)Br)Br)Br
• Canonical SMILES: Brc1c(Br)c(Br)c2c(c1Br)[nH]cn2
• InChI: InChI=1S/C7H2Br4N2/c8-2-3(9)5(11)7-6(4(2)10)12-1-13-7/h1H,(H,12,13)
• InChIKey: LOEIRDBRYBHAJB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,5,6,7-tetrabromo-1H-1,3-benzodiazole
• IUPAC Traditional name: 4,5,6,7-tetrabromo-1H-1,3-benzodiazole
• Synonyms: 4,5,6,7-Tetrabromobenzimidazole; TBBz; TBBz; 4,5,6,7-Tetrabromobenzimidazole

Database IDs

• CAS Number: 577779-57-8
• MDL Number: MFCD04116202
• PubChem SID: 162248143
• PubChem CID: 5149739

CALCULATED PROPERTIES

• Acid pKa: 10.666
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.2870874
• LogD (pH = 7.4): 4.3336635
• Log P: 4.3345146
• Molar Refractivity: 65.4597 cm^3
• Polarizability: 26.760044 Å^3
• Polar Surface Area: 28.68 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL at 60 °C, clear; Ethanol; Methanol
• Apperance: Light Yellow Solid; powder
• Melting Point: 330-332°C

Safety Information

• Storage Condition: -20°C Freezer; under inert gas
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36
• Safety Statements: 26-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H319
• GHS Precautionary statements: P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C7H2N2Br4

DETAILS

Sigma Aldrich - T6951

Biochem/physiol Actions
TBBz is a cell-permeable Casein Kinase-2 (CK2) inhibitor. CK2 inhibitors, 4,5,6,7-tetrabromobenzotriazole (TBBt, Sigma Cat. # T0826) and rabromobenzimidazole (TBBz), the latter of which was shown to discriminate between different molecular forms of CK2 in yeast. TBBt, with a pK(a) ~5, exists in solution at physiological pH almost exclusively (>99%) as the monoanion; whereas TBBz, with a pKa ~9, is predominantly (>95%) in the neutral form, both of obvious relevance to their modes of binding. In vitro, TBBt inhibits different forms of CK2 with Ki values ranging from 80 to 210 nM. TBBz discriminates better between CK2 forms, with Ki values ranging from 70-510 nM. TBBz is more effective than TBBt in inducing apoptosis and to a lesser degree, necrosis in transformed human cell lines. Dvelopment of shRNA strategies for the selective knockdown of the CK2α and CK2α′ isoforms reinforces the foregoing results, indicating that inhibition of CK2 leads to attenuation of proliferation.

Toronto Research Chemicals - T291150

A selective ATP-competitive inhibitor of protein kinase CK2 from such divergent sources as yeast, rat liver, Neurospora erassa and Candida tropicalis, with Ki values in the range of 0.5-1uM. It is virtually inactive against PKA, PKC, and a very weak inhi

REFERENCES

• Zien, P., et al.: Biochemical and Biophysical Res. Commun., 306, 129 (2003)