B4380

Bromobimane

≥97%

• Synonym(s): Monobromobimane
• Empirical Formula (Hill Notation): C₁₀H₁₁BrN₂O₂
• CAS Number: 71418-44-5
• Molecular Weight: 271.11
• Beilstein: 4430959
• MDL number: MFCD00036951
• PubChem Substance ID: 24891769
• NACRES: NA.47

Properties

• Quality Level: 200
• Assay: ≥97%
• form: powder
• mp: 161 °C
• solubility: acetonitrile: 20 mg/mL
• ε (extinction coefficient): 4.6-5.1 at 396-398 nm in H₂O
• application(s): diagnostic assay manufacturing; hematology; histology
• storage temp.: −20°C
• SMILES string: CC1=C(C)C(=O)N2N1C(CBr)=C(C)C2=O
• InChI: 1S/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3
• InChI key: AHEWZZJEDQVLOP-UHFFFAOYSA-N

Description

General description

Bromobimane is also known as monobromobimane. It is also a known probe for thiols and is a fluorescent reagent activated upon a photolysis reaction.

Application

Bromobimane is used for the determination of thiols by the HPLC method. It is suitable as a pre-column derivatization agent for fluorometric determination of 2,3-dimercaptopropane-1-sulfonic acid and other dithiols. Bromobimane has been used as a fluorescent label in studying oligomycin-sensitive ATPase from beef heart mitochondria.
Bromobimane has been used for the quantitative measurement of free hydrogen sulfide in vivo and in vitro. It has been used for the labeling of proteins containing thiol groups.

Biochem/physiol Actions

Bromobimane in solution reacts with small thiol groups (e.g., GSH) and with reactive protein thiol groups (e.g., hemoglobin). The reaction of Bromobimane with thiols is of second-order and dependent on pH and upon reacting with thiolate, it activates the water-soluble fluorescent product for detection.

Safety Information

• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves