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A6057

Sigma-Aldrich

4-Azidophenacyl bromide

powder

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C8H6BrN3O
Numero CAS:
57018-46-9
Peso molecolare:
240.06
Beilstein:
1961705
Numero CE:
260-519-5
Numero MDL:
MFCD00042637
Codice UNSPSC:
12352100
ID PubChem:
57653867
NACRES:
NA.22

Forma fisica

powder

Impiego in reazioni chimiche

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

Colore

yellow

Solubilità

methanol: 50 mg/mL

Temperatura di conservazione

2-8°C

Stringa SMILE

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
LZJPDRANSVSGOR-UHFFFAOYSA-N

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Applicazioni

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.

Avvertenza

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.

Avvertenze

Danger

Indicazioni di pericolo

H228,H314,H317,H334

Classi di pericolo

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

Codice della classe di stoccaggio

4.1B - Flammable solid hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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Sigma-Aldrich

776130

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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
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
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
L M Hsu et al.
Journal of molecular biology, 172(1), 57-76 (1984-01-05)
tRNAPhe and tRNAVal of Escherichia coli were derivatized at the S4U8 position with p-azidophenacyl and p-azidophenacylacetate photoaffinity probes. The modified tRNAs could still function efficiently in all of the partial reactions of protein synthesis except for an approximately sevenfold decrease
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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