3-(bromomethyl)-2,5,6-trimethyl-1H,7H-[1,2]diazolo[1,2-a]pyrazole-1,7-dione

• ChemBase ID: 126251
• Molecular Formular: C10H11BrN2O2
• Molecular Mass: 271.11054
• Monoisotopic Mass: 270.0003896
• SMILES: O=c1c(c(n2c(c(c(=O)n12)C)CBr)C)C
• Canonical SMILES: BrCc1c(C)c(=O)n2n1c(C)c(c2=O)C
• InChI: InChI=1S/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3
• InChIKey: AHEWZZJEDQVLOP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(bromomethyl)-2,5,6-trimethyl-1H,7H-[1,2]diazolo[1,2-a]pyrazole-1,7-dione
• IUPAC Traditional name: monobromobimane
• Synonyms: Bromobimane; mBBr; Bromobimane; Monobromobimane; Bromobimane; Monobromobimane

Database IDs

• CAS Number: 71418-44-5
• MDL Number: MFCD00036951
• Beilstein Number: 4430959
• PubChem SID: 24885999; 24891769; 162220590
• PubChem CID: 114810
• Chemspider ID: 102775
• Wikipedia Title: Bromobimane

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.108555
• LogD (pH = 7.4): 1.108555
• Log P: 1.108555
• Molar Refractivity: 61.784 cm^3
• Polarizability: 22.485628 Å^3
• Polar Surface Area: 40.62 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble; Dichloromethane; DMF: soluble; DMSO; DMSO: soluble; in MeOH, DMF, DMSO; Methanol; methanol: soluble
• Apperance: Yellow Solid
• Melting Point: 152-154 °C(lit.); 152–154 °C; 160-161°C (dec.)
• Fluorescence: λex 390 nm; λem 478 nm in 0.1 M phosphate pH 7.5 (after derivatization with glutathione); λex 398 nm

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Light Sensitive
• German water hazard class: 3
• Main Hazard: alkylating agent
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95% (HPCE); ≥97%
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C10H11BrN2O2

DETAILS

Sigma Aldrich - 69898

Application
suitable for the detection of thiol-groups.
Other Notes
Fluorescent thiol-specific reagent1,2

Sigma Aldrich - B4380

Application
Fluorescent probe for thiols

Toronto Research Chemicals - M525000

Monobromobimane readily reacts with low molecular weight thiols. Bimanes are useful for detecting the distribution of protein thiols in cells before and after chemical reduction of disulfides.Fluorescence: max. Abs. 398nm; e x 10-3: 5.0

REFERENCES

• Kosower, N.S., et al.: Proc. Nat. Acad. Sci. USA, 76, 3382 (1979)
• Danielsohn, P., et al.: Histochem., 86, 281 (1979)
• Mol. Reprod. Devel. 37, 318 (1994)