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779318

Sigma-Aldrich

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:
3302-39-4
Molecular Weight:
198.02
Beilstein:
1941487
MDL number:
MFCD11207352
UNSPSC Code:
12352200
PubChem Substance ID:
329768026
form:
solution
Assay:
≥95.0% (HPLC)
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Assay

≥95.0% (HPLC)

form

solution

concentration

~0.5 M in tert-butyl methyl ether

impurities

≤2.0% water

storage temp.

−20°C

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

General description

1-Azido-2-bromobenzene is an aromatic azide generally used in copper(I)-catalyzed azide-alkyne cycloaddition reactions.[1] It can also undergo palladium-catalyzed cross-coupling with arylboronic acids to form the corresponding azido-bis-aryl derivatives.[2]

Application

Review[3]

Signal Word

Danger

Hazard Statements

H225,H315,H319,H372

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT RE 1

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-27.4 °F

Flash Point(C)

-33 °C

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD4548V
BCBD4548

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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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