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B4380

Sigma-Aldrich

Bromobimane

≥97% purity, powder

Synonym(s):

Monobromobimane

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About This Item

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

product name

Bromobimane, ≥97% (HPLC)

Quality Level

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

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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.

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000385726
0000369257
0000369257
0000385726
SLCC7229

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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)
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
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
Michael Hall et al.
Proteomics, 10(5), 987-1001 (2010-01-06)
The light-dependent regulation of stromal enzymes by thioredoxin (Trx)-catalysed disulphide/dithiol exchange is known as a classical mechanism for control of chloroplast metabolism. Recent proteome studies show that Trx targets are present not only in the stroma but in all chloroplast
Carl Simonsson et al.
The Journal of investigative dermatology, 131(7), 1486-1493 (2011-01-14)
Allergic contact dermatitis (ACD) is the most prevalent form of human immunotoxicity. It is caused by skin exposure to haptens, i.e., protein-reactive, low-molecular-weight chemical compounds, which form hapten-protein complexes (HPCs) in the skin, triggering the immune system. These immunogenic HPCs
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