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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:
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 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

B4380-25MG:
B4380-VAR:
B4380-100MG:
B4380-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
SLBF5769V
SLCC7229
SLBZ5697
SLBW9269
SLBS0772V

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Bromobimane probes for thiols.
E M Kosower et al.
Methods in enzymology, 251, 133-148 (1995-01-01)
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
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)
Xiao Jie Yao et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(23), 9501-9506 (2009-05-28)
G protein-coupled receptors (GPCRs) mediate the majority of physiologic responses to hormones and neurotransmitters. However, many GPCRs exhibit varying degrees of agonist-independent G protein activation. This phenomenon is referred to as basal or constitutive activity. For many of these GPCRs
Edward A Wintner et al.
British journal of pharmacology, 160(4), 941-957 (2010-07-02)
Hydrogen sulphide (H(2)S) is a labile, endogenous metabolite of cysteine, with multiple biological roles. The development of sulphide-based therapies for human diseases will benefit from a reliable method of quantifying H(2)S in blood and tissues. Concentrations of reactive sulphide in
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