779318
1-Azido-2-bromobenzene solution
~0.5 M in tert-butyl methyl ether
Synonym(s):
2-Bromophenyl azide solution
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About This Item
Empirical Formula (Hill Notation):
C6H4BrN3
CAS Number:
Molecular Weight:
198.02
PubChem Substance ID:
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
1941487
MDL number:
Assay:
≥95.0% (HPLC)
Form:
solution
SMILES string
Brc1ccccc1N=[N+]=[N-]
InChI
1S/C6H4BrN3/c7-5-3-1-2-4-6(5)9-10-8/h1-4H
InChI key
QOVQEONXPGQIHT-UHFFFAOYSA-N
assay
≥95.0% (HPLC)
form
solution
concentration
~0.5 M in tert-butyl methyl ether
impurities
≤2.0% water
storage temp.
−20°C
General description
1-Azido-2-bromobenzene is an aromatic azide generally used in copper(I)-catalyzed azide-alkyne cycloaddition reactions. It can also undergo palladium-catalyzed cross-coupling with arylboronic acids to form the corresponding azido-bis-aryl derivatives.
Application
Review
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT RE 1
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
-27.4 °F
flash_point_c
-33 °C
Regulatory Information
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First Suzuki?Miyaura type cross-coupling of ortho-azidobromobenzene with arylboronic acids and its application to the synthesis of fused aromatic indole-heterocycles
Pudlo M, et al.
Tetrahedron, 63(41), 10320-10329 (2007)
Cu-catalyzed azide? alkyne cycloaddition
Meldal M & Torn?e CW
Chemical Reviews, 108(8), 2952-3015 (2008)
Stefan Bräse et al.
Angewandte Chemie (International ed. in English), 44(33), 5188-5240 (2005-08-16)
Since the discovery of organic azides by Peter Griess more than 140 years ago, numerous syntheses of these energy-rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide
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