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34025

Sigma-Aldrich

Dibromobimane

BioReagent, suitable for fluorescence, ≥95.0% (CHN)

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About This Item

Empirical Formula (Hill Notation):
C10H10Br2N2O2
CAS Number:
68654-25-1
Molecular Weight:
350.01
Beilstein/REAXYS Number:
4189453
MDL number:
MFCD00036952
UNSPSC Code:
12352108
PubChem Substance ID:
57649022
NACRES:
NA.32

product line

BioReagent

Quality Level

100

assay

≥95.0% (CHN)

mp

170-172 °C (lit.)

solubility

DMF: soluble
acetonitrile: soluble
chloroform: soluble

fluorescence

λex 391 nm in methanol
λex 393 nm; λem 477 nm in 0.1 M Tris pH 7.0, gutathione red

suitability

suitable for fluorescence

storage temp.

2-8°C

SMILES string

CC1=C(CBr)N2N(C1=O)C(=O)C(C)=C2CBr

InChI

1S/C10H10Br2N2O2/c1-5-7(3-11)13-8(4-12)6(2)10(16)14(13)9(5)15/h3-4H2,1-2H3

InChI key

OSIYFMVMZXJKSP-UHFFFAOYSA-N

Application

Dibromobimane, a bifunctional thiol reagent, is used as a cross-linking agent for cysteine mapping and studies on protein structure/conformation and cross-linking processes.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Fluorescent thiol-specific labeling reagent

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Zhenhui Chen et al.
The Journal of biological chemistry, 281(20), 14163-14172 (2006-03-24)
Interactions between the transmembrane domains of phospholamban (PLB) and the cardiac Ca2+ pump (SERCA2a) have been investigated by chemical cross-linking. Specifically, C-terminal, transmembrane residues 45-52 of PLB were individually mutated to Cys, then cross-linked to V89C in the M2 helix
E Kim et al.
Journal of molecular biology, 299(2), 421-429 (2000-06-22)
The DNase I binding loop (residues 38-52), the hydrophobic plug (residues 262-274), and the C terminus region are among the structural elements of monomeric (G-) actin proposed to form the intermonomer interface in F-actin. To test the proximity and interactions
Hai Po Helena Liang et al.
The Biochemical journal, 437(3), 455-460 (2011-05-21)
TF (tissue factor) is a transmembrane cofactor that initiates blood coagulation in mammals by binding Factor VIIa to activate Factors X and IX. The cofactor can reside in a cryptic configuration on primary cells and de-encryption may involve a redox
Wiebke Albrecht et al.
Archives of toxicology, 93(6), 1609-1637 (2019-06-30)
Drug-induced liver injury (DILI) cannot be accurately predicted by animal models. In addition, currently available in vitro methods do not allow for the estimation of hepatotoxic doses or the determination of an acceptable daily intake (ADI). To overcome this limitation
H Bhattacharjee et al.
The Journal of biological chemistry, 271(40), 24465-24470 (1996-10-04)
ArsA ATPase activity is allosterically activated by salts of the semimetal arsenic or antimony. Activation is associated with the presence of three cysteine residues in ArsA: Cys113, Cys172, and Cys422. To determine the distance between cysteine residues, wild type ArsA
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