B4380

Bromobimane

≥97% purity, powder

• Synonym(s): Monobromobimane
• Empirical Formula (Hill Notation): C₁₀H₁₁BrN₂O₂
• CAS Number: 71418-44-5
• Molecular Weight: 271.11
• NACRES: NA.47
• PubChem Substance ID: 24891769
• UNSPSC Code: 12171500
• MDL number: MFCD00036951
• Beilstein/REAXYS Number: 4430959

Properties

• Product Name: Bromobimane, ≥97% (HPLC)
• Quality Segment: 200
• assay: ≥97% (HPLC)
• form: powder
• color: yellow
• 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.[1] 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: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)