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B4380

Sigma-Aldrich

Bromobimane

≥97% purity, powder

Synonyme(s) :

Monobromobimane

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About This Item

Formule empirique (notation de Hill):
C10H11BrN2O2
Numéro CAS:
71418-44-5
Poids moléculaire :
271.11
Numéro Beilstein :
4430959
Numéro MDL:
MFCD00036951
Code UNSPSC :
12171500
ID de substance PubChem :
24891769
Nomenclature NACRES :
NA.47

product name

Bromobimane, ≥97% (HPLC)

Niveau de qualité

200

Pureté

≥97% (HPLC)

Forme

powder

Couleur

yellow

Pf

161 °C

Solubilité

acetonitrile: 20 mg/mL

ε (coefficient d'extinction)

4.6-5.1 at 396-398 nm in H2O

Application(s)

diagnostic assay manufacturing
hematology
histology

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

AHEWZZJEDQVLOP-UHFFFAOYSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000385726
0000369257
0000369257
0000385726
SLCC7229

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A method based on the differential reactivity of thiol and thiolate with monobromobimane (mBBr) has been developed to measure nucleophilicity and acidity of protein and low-molecular-weight thiols. Nucleophilicity of the thiolate is measured as the pH-independent second-order rate constant of
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