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Sigma-Aldrich

1-Bromo-4-nitrobenzene

99%

Synonym(s):

1-Bromo-4-nitrobenzene, 1-Nitro-4-bromobenzene, 4-Bromo-1-nitrobenzene, 4-Nitro-1-bromobenzene, 4-Nitrobromobenzene, 4-Nitrophenyl bromide, p-Bromonitrobenzene, p-Nitrophenyl bromide

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About This Item

Linear Formula:
BrC6H4NO2
CAS Number:
586-78-7
Molecular Weight:
202.01
Beilstein:
636964
EC Number:
209-583-8
MDL number:
MFCD00007280
UNSPSC Code:
12352100
PubChem Substance ID:
24850195
NACRES:
NA.22

Assay

99%

form

solid

bp

255-256 °C (lit.)

mp

124-126 °C (lit.)

SMILES string

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

InChI

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

InChI key

ZDFBKZUDCQQKAC-UHFFFAOYSA-N

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General description

Electrochemical reduction of 1-bromo-4-nitrobenzene at zinc microelectrodes in ionic liquid has been investigated by cyclic voltammetry. 1-Bromo-4-nitrobenzene undergoes palladium-catalyzed Stille cross coupling reaction with furan-2-yltributyltin using Dabco(triethylenediamine) as ligand. It reacts with p-cresol to yield 1-methyl-4-(4-nitrophenoxy)benzene.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jin-Heng Li et al.
The Journal of organic chemistry, 70(7), 2832-2834 (2005-03-25)
[reaction: see text] An efficient Pd(OAc)2/Dabco-catalyzed Stille cross-coupling reaction procedure has been developed. In the presence of Pd(OAc)2 and Dabco (triethylenediamine), various aryl halides including aryl iodides, aryl bromides, and activated aryl chlorides were coupled efficiently with organotin compounds to
Evgeniy G Gordeev et al.
PloS one, 13(6), e0198370-e0198370 (2018-06-08)
Additive manufacturing with fused deposition modeling (FDM) is currently optimized for a wide range of research and commercial applications. The major disadvantage of FDM-created products is their low quality and structural defects (porosity), which impose an obstacle to utilizing them
Synthesis of diaryl ethers using an easy-to-prepare, air-stable, soluble copper (I) catalyst.
Gujadhur R and Venkataraman D.
Synthetic Communications, 31(18), 2865-2879 (2001)
Sven Ernst et al.
Physical chemistry chemical physics : PCCP, 16(10), 4478-4482 (2014-01-30)
The electrochemical reduction of 1-bromo-4-nitrobenzene (p-BrC6H4NO2) at zinc microelectrodes in the [C4mPyrr][NTf2] ionic liquid was investigated via cyclic voltammetry. The reduction was found to occur via an EC type mechanism, where p-BrC6H4NO2 is first reduced by one electron, quasi-reversibly, to
Xiao Yan et al.
Physical chemistry chemical physics : PCCP, 22(11), 6222-6230 (2020-03-05)
Unveiling the reaction mechanism is significant for developing high-performance catalysts. In this paper, a series of precisely controlled PdxM147-x (M = Cu, Pt, Au, Rh, Ru) dendrimer encapsulated nanoparticles (DENs) has been successfully synthesized. The mechanisms of PdxM147-x as catalysts
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