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A6057

Sigma-Aldrich

4-Azidophenacyl bromide

powder

Synonym(s):

4′-Azido-2-bromoacetophenone, 4-Azido-α-bromoacetophenone

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About This Item

Empirical Formula (Hill Notation):
C8H6BrN3O
CAS Number:
57018-46-9
Molecular Weight:
240.06
Beilstein:
1961705
EC Number:
260-519-5
MDL number:
MFCD00042637
UNSPSC Code:
12352100
PubChem Substance ID:
57653867
NACRES:
NA.22

form

powder

reaction suitability

reaction type: click chemistry
reagent type: cross-linking reagent

color

yellow

solubility

methanol: 50 mg/mL

storage temp.

2-8°C

SMILES string

BrCC(=O)c1ccc(cc1)N=[N+]=[N-]

InChI

1S/C8H6BrN3O/c9-5-8(13)6-1-3-7(4-2-6)11-12-10/h1-4H,5H2

InChI key

LZJPDRANSVSGOR-UHFFFAOYSA-N

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Application

Photoactive, heterobifunctional cross-linking reagent. Typically, the initial reaction couples to sulfhydryl in the pH range 7.0-8.0. Second bonding occurs during UV irradiation (250 nm) via reactive nitrene. The latter bonding is rapid and non-specific.

Caution

Reducing agents such as thiols may reduce the azide to amine and should be avoided. Initial manipulations and coupling should be performed under reduced light.

Signal Word

Danger

Hazard Statements

H228,H314,H317,H334

Hazard Classifications

Eye Dam. 1 - Flam. Sol. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S H Hixson et al.
Biochemistry, 14(19), 4251-4254 (1975-09-23)
The synthesis of the photochemically labile bifunctional reagent p-azidophenacyl bromide (1) is described. This compound may be covalently attached to a known site of an enzyme or other macromolecule by nucleophilic displacement at the alpha-bromo ketone moiety. Subsequent irradiation of
D Hu et al.
The Journal of biological chemistry, 275(4), 2705-2712 (2000-01-25)
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Nan Zhang et al.
Nucleic acids research, 37(18), 5981-5992 (2009-08-21)
sigma(54)-dependent transcription requires activation by bacterial enhancer binding proteins (bEBPs). bEBPs are members of the AAA+ (ATPases associated with various cellular activities) protein family and typically form hexameric structures that are crucial for their ATPase activity. The precise mechanism by
M A Cassetti et al.
Proceedings of the National Academy of Sciences of the United States of America, 93(15), 7540-7545 (1996-07-23)
The vaccinia virus early transcription factor (VETF), a heterodimeric protein composed of 82- and 70-kDa subunits, interacts with viral early promoters at both a sequence-specific core region upstream and a sequence-independent region downstream of the RNA start site. To determine
A Robinson et al.
The Biochemical journal, 242(3), 767-777 (1987-03-15)
An azidophenacyl derivative of a chemically synthesized consensus signal peptide has been prepared. The peptide, when photoactivated in the presence of rough or high-salt-stripped microsomes from pancreas, leads to inhibition of their activity in cotranslational processing of secretory pre-proteins translated
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