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Merck
CN

B8271

Bromoacetic acid N-hydroxysuccinimide ester

≥95%, powder

Synonym(s):

2,5-Dioxopyrrolidin-1-yl 2-bromoacetate, N-Hydroxysuccinimide bromoacetate

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About This Item

Empirical Formula (Hill Notation):
C6H6BrNO4
CAS Number:
42014-51-7
Molecular Weight:
236.02
NACRES:
NC.07
PubChem Substance ID:
24892067
UNSPSC Code:
12352106
MDL number:
MFCD00058571

Key Documents

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Product Name

Bromoacetic acid N-hydroxysuccinimide ester, ≥95%, powder

InChI

1S/C6H6BrNO4/c7-3-6(11)12-8-4(9)1-2-5(8)10/h1-3H2

SMILES string

O=C(N1OC(CBr)=O)CCC1=O

InChI key

NKUZQMZWTZAPSN-UHFFFAOYSA-N

assay

≥95%

form

powder

reaction suitability

reagent type: cross-linking reagent

solubility

acetone: 25 mg/mL
DMF: soluble

functional group

NHS ester

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

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Application

A heterobifunctional cross-linking reagent which allows bromoacetylation of primary amine groups followed by coupling to sulfhydryl-containing compounds. Typically, initial reaction couples via ester to primary amine by amide bond formation in the pH range 6.5-8.5. The second reaction results in thioether bonding in pH range 7.0-8.0.

Disclaimer

The bromoacetyl group is light sensitive.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000461197
0000461197
0000342594
0000342594
0000367505

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N Kolodny et al.
Analytical biochemistry, 187(1), 136-140 (1990-05-15)
A method described here for conjugating synthetic peptides to carrier proteins provides a convenient method for determining peptide-to-carrier protein ratios. N-Bromoacetyl-containing peptides are reacted in situ with carrier proteins in which the disulfide bonds were reduced with tri-n-butylphosphine. At pH
John S Mort et al.
Methods in molecular medicine, 100, 237-250 (2004-07-29)
The use of synthetic peptides to generate rabbit polyclonal anticatabolic neoepitope antibodies that can be used to study the presence of defined proteolytic cleavage sites in aggrecan is described. Principles of peptide design and methods for preparation and characterization of
M S Bernatowicz et al.
Analytical biochemistry, 155(1), 95-102 (1986-05-15)
Synthetic peptides derived from human fibrin were unidirectionally conjugated to three carrier proteins (bovine serum albumin, bovine alpha-lactalbumin, and keyhole limpet hemocyanin) by a method that employs N-succinimidyl bromoacetate. This heterobifunctional crosslinking reagent was prepared with a 79% yield in

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