Bromobimane

Bromobimane


IUPAC name 3-(bromomethyl)-2,5,6-trimethyl-1H,7H- pyrazolo[1,2-a]pyrazole-1,7-dione
Other names Bromobimane, mBBr
Identifiers
CAS number	71418-44-5^Y
PubChem	114810
ChemSpider	102775^Y
Jmol-3D images	Image 1
SMILES O=C1\C(=C(/N2/C(=C(\C(=O)N12)C)CBr)C)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^Y Key: AHEWZZJEDQVLOP-UHFFFAOYSA-N^Y InChI=1/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3 Key: AHEWZZJEDQVLOP-UHFFFAOYAR
Properties
Molecular formula	C₁₀H₁₁BrN₂O₂
Molar mass	271.11 g mol⁻¹
Melting point	152–154 °C
Solubility in water	in MeOH, DMF, DMSO
Hazards
Main hazards	alkylating agent
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Bromobimane (or monobromobimane) is a heterocyclic compound and bimane dye that is used as a reagent in biochemistry. It alkylates thiol groups, replacing the H with a fluorescent tag (λ_emission = 478 nm). Its alkylating properties are comparable to iodoacetamide.^[1]

References

^ Paul C. Chinn, Vincent Pigiet, and Robert C. Fahey (1986). "Determination of thiol proteins using monobromobimane labeling and high-performance liquid chromatographic analysis: Application to Escherichia coli thioredoxin". Analytical Biochemistry 159 (1): 143–149. doi:10.1016/0003-2697(86)90319-2. PMID 3544950.