B4380
Bromobimane
≥97% purity, powder
Synonym(s):
Monobromobimane
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About This Item
Empirical Formula (Hill Notation):
C10H11BrN2O2
CAS Number:
Molecular Weight:
271.11
Beilstein:
4430959
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47
Product Name
Bromobimane, ≥97% (HPLC)
Quality Level
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
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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.
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.
Storage Class Code
11 - 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
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Differing effects of mechanical dough development and sheeting development methods on aggregated glutenin proteins.
Sutton KH, et al.
Cereal Chem., 80.6, 707-711 (2003)
Brigitte Bauer et al.
Chemical research in toxicology, 24(5), 737-743 (2011-04-14)
Allergic contact dermatitis is the most prevalent form of human immunotoxicity. It is caused by reactive low molecular weight chemicals, that is, haptens, coming in contact with the skin where hapten-peptide complexes are formed, activating the immune system. By using
N S Kosower et al.
Proceedings of the National Academy of Sciences of the United States of America, 76(7), 3382-3386 (1979-07-01)
The bimane fluorescent labels, monobromobimane, dibromobimane, and monobromotrimethylammoniobimane, are derivatives of syn-9,10-dioxabimane:1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione. They efficiently label hemoglobin (reactive thiol groups), membrane proteins, and glutathione of normal human red cells under physiological conditions. Monobromobimane and dibromobimane are effective on intact cells while
Bromobimane probes for thiols.
E M Kosower et al.
Methods in enzymology, 251, 133-148 (1995-01-01)
Florencia Sardi et al.
Analytical biochemistry, 435(1), 74-82 (2013-01-09)
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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