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Merck
CN

A6057

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57653867
EC Number:
260-519-5
Beilstein/REAXYS Number:
1961705
MDL number:
MFCD00042637

Key Documents

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InChI key

LZJPDRANSVSGOR-UHFFFAOYSA-N

InChI

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

SMILES string

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

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

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.

Disclaimer

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.

signalword

Danger

Hazard Classifications

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

Storage Class

4.1B - Flammable solid hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000042630
0000001838
BGBB8607
R015280/1V
015280/1

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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
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
J L Chen et al.
The EMBO journal, 17(5), 1515-1525 (1998-04-18)
Bacterial ribonuclease P contains a catalytic RNA subunit that cleaves precursor sequences from the 5' ends of pre-tRNAs. The RNase P RNAs from Bacillus subtilis and Escherichia coli each contain several unique secondary structural elements not present in the other.
Structure determination by directed photo-cross-linking in large RNA molecules with site-specific psoralen.
D Mundus et al.
Methods in enzymology, 318, 104-118 (2000-07-13)
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