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A6057

Sigma-Aldrich

4-Azido-phenacylbromid

powder

Synonym(e):

4′-Azido-2-brom-acetophenon, 4-Azido-α-brom-acetophenon

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About This Item

Empirische Formel (Hill-System):
C8H6BrN3O
CAS-Nummer:
57018-46-9
Molekulargewicht:
240.06
Beilstein:
1961705
EG-Nummer:
260-519-5
MDL-Nummer:
MFCD00042637
UNSPSC-Code:
12352100
PubChem Substanz-ID:
57653867
NACRES:
NA.22

Form

powder

Eignung der Reaktion

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

Farbe

yellow

Löslichkeit

methanol: 50 mg/mL

Lagertemp.

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

InChIKey

LZJPDRANSVSGOR-UHFFFAOYSA-N

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Anwendung

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.

Vorsicht

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.

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Analysenzertifikate (COA)

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3-Azido-1-propanol ≥96%

Sigma-Aldrich

776130

3-Azido-1-propanol

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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)
The PI-SceI protein is an intein-encoded homing endonuclease that initiates the mobility of its gene by making a double strand break at a single site in the yeast genome. The PI-SceI protein splicing and endonucleolytic active sites are separately located
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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