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B57400

Sigma-Aldrich

4-Bromobenzaldehyde

ReagentPlus®, 99%

Synonym(s):

1-Bromo-4-formylbenzene, 4-Bromobenzaldehyde, 4-Bromobenzenealdehyde, 4-Formyl-1-bromobenzene, 4-Formylbromobenzene, 4-Formylphenyl bromide, p-Bromobenzaldehyde, p-Formylbromobenzene

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About This Item

Linear Formula:
BrC6H4CHO
CAS Number:
1122-91-4
Molecular Weight:
185.02
Beilstein/REAXYS Number:
507100
EC Number:
214-365-0
MDL number:
MFCD00003377
UNSPSC Code:
12352100
PubChem Substance ID:
24891856
NACRES:
NA.22

Quality Level

200

product line

ReagentPlus®

assay

99%

form

crystals

mp

55-58 °C (lit.)

SMILES string

[H]C(=O)c1ccc(Br)cc1

InChI

1S/C7H5BrO/c8-7-3-1-6(5-9)2-4-7/h1-5H

InChI key

ZRYZBQLXDKPBDU-UHFFFAOYSA-N

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Application

4-Bromobenzaldehyde can be used as a reactant:
  • To synthesize vinyl esters by reacting with terminal alkynoates in the presence of triphenylphosphine catalyst.
  • In the palladium-catalyzed Mizoroki-Heck Cross-coupling reaction with styrene to synthesize arylated olefins.
  • In the Suzuki-Wittig reaction with formylphenylboronic acids to synthesize dimethyl biphenyl-diacrylates.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

228.2 °F - closed cup

flash_point_c

109 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD2523V
WXBD1571V
WXBD0893V
WXBC9374V
WXBC8917V

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Gary A Molander et al.
The Journal of organic chemistry, 71(26), 9681-9686 (2006-12-16)
We have previously reported that the palladium-catalyzed cross-coupling reaction of potassium vinyltrifluoroborate with aryl electrophiles proceeds with good yields. Herein, we describe recent progress in optimizing the reaction, as well as outlining the scope and limitations of the reaction. The
Tetrahedron Letters, 48, 539-539 (2007)
Timo Rhauderwiek et al.
Chemical science, 9(24), 5467-5478 (2018-07-17)
The Ni-metallated porphyrin-based tetraphosphonic acid (Ni-tetra(4-phosphonophenyl)porphyrin, Ni-H8TPPP) was used for the synthesis of highly porous metal phosphonates containing the tetravalent cations Zr4+ and Hf4+. The compounds were thoroughly characterized regarding their sorption properties towards N2 and H2O as well as
Gugu Kubheka et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 191, 357-364 (2017-10-22)
The optical limiting (OL) properties of 3,5-dipyrenylvinyleneBODIPY dyes that contain both electron withdrawing and donating moieties have been investigated by using the z-scan technique at 532nm in the nanosecond pulse range. The extension of the π-conjugation at the 3,5-positions with
Ved Vati Singh et al.
Dalton transactions (Cambridge, England : 2003), 44(2), 725-732 (2014-11-20)
The metastable tetragonal Cu2Se phase as nanoflakes has been synthesized for the first time by treating CuCl2 taken in a mixture (1:1) of 1-octadecene and oleylamine with H2N-(CH2)3-SePh dissolved in 1-octadecene. Powder X-ray diffraction (PXRD), HRTEM, SEM-EDX and XPS have

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