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365424

Sigma-Aldrich

1-Bromo-2-nitrobenzene

98%

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About This Item

Linear Formula:
BrC6H4NO2
CAS Number:
577-19-5
Molecular Weight:
202.01
Beilstein/REAXYS Number:
2044109
EC Number:
209-409-0
MDL number:
MFCD00007045
UNSPSC Code:
12352100
PubChem Substance ID:
24862518
NACRES:
NA.22

Quality Level

200

assay

98%

bp

261 °C (lit.)

mp

40-42 °C (lit.)

functional group

bromo
nitro

storage temp.

2-8°C

SMILES string

[O-][N+](=O)c1ccccc1Br

InChI

1S/C6H4BrNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H

InChI key

ORPVVAKYSXQCJI-UHFFFAOYSA-N

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General description

1-Bromo-2-nitrobenzene undergoes palladium[0]-mediated Ullmann cross-coupling reaction with a range of β-halo-enals, -enones or -esters to afford the corresponding β-aryl derivatives. Palladium[0]-mediated Ullmann cross-coupling reaction of 1-bromo-2-nitrobenzene with β-bromo-α,β-unsaturated aldehydes is reported.

Application

1-Bromo-2-nitrobenzene may be used in the preparation of:
  • 4-methoxy-2′-nitrodiphenyl ether
  • 1-methoxy-3,5-bis-(2-nitro-phenoxy)benzene
  • 5-hydroxy-3-methoxy-2′-nitrodiphenyl ether

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBM2722V
1421168V
1420732V
1421168
1420732

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1-Bromo-2,4-dinitrobenzene 97%

Sigma-Aldrich

262226

1-Bromo-2,4-dinitrobenzene

Martin G Banwell et al.
Organic letters, 6(16), 2741-2744 (2004-07-30)
Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of beta-halo-enals, -enones, or -esters readily affords the corresponding beta-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with
4-Hydroxy-2'-Nitrodiphenyl Ether Analogues as Novel Tyrosinase Inhibitors.
Sapkota K, et al.
Bull. Korean Chem. Soc., 31(5), 1319-1319 (2010)
New protocols for the synthesis of 3, 4-annulated and 4-substituted quinolines from ?-bromo-a, ?-unsaturated aldehydes and 1-bromo-2-nitrobenzene or 2-bromoacetanilide.
Some S, et al.
Tetrahedron Letters, 48(20), 3609-3612 (2007)
Luka A Wright et al.
Dalton transactions (Cambridge, England : 2003), 44(16), 7230-7241 (2015-03-20)
The 2-(2′-aniline)-6-imine-pyridines, 2-(C6H4-2′-NH2)-6-(CMe=NAr)C5H3N (Ar = 4-i-PrC6H4 (HL1a), 2,6-i-Pr2C6H3 (HL1b)), have been synthesised via sequential Stille cross-coupling, deprotection and condensation steps from 6-tributylstannyl-2-(2-methyl-1,3-dioxolan-2-yl)pyridine and 2-bromonitrobenzene. The palladium(II) acetate N,N,N-pincer complexes, [{2-(C6H4-2′-NH)-6-(CMe=NAr)C5H3N}Pd(OAc)] (Ar = 4-i-PrC6H4 (1a), 2,6-i-Pr2C6H3 (1b)), can be prepared by

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