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124915

Sigma-Aldrich

4-Formylbenzoic acid

97%

Synonym(s):

4-Carboxybenzaldehyde, Benzaldehyde-4-carboxylic acid, Terephthalaldehydic acid

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About This Item

Linear Formula:
HO2CC6H4CHO
CAS Number:
619-66-9
Molecular Weight:
150.13
Beilstein:
471734
EC Number:
210-607-4
MDL number:
MFCD00006951
UNSPSC Code:
12352100
PubChem Substance ID:
24847634
NACRES:
NA.22

Quality Level

100

Assay

97%

form

powder

mp

247 °C (lit.)

SMILES string

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

InChI

1S/C8H6O3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H,(H,10,11)

InChI key

GOUHYARYYWKXHS-UHFFFAOYSA-N

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General description

4-Formylbenzoic acid is an important intermediate in the synthesis of terepthalic acid. It reacts with barium carbonate to yield two-dimensional barium(II) coordination polymer.

Application

4-Formylbenzoic acid has been used as reagent during esterification of 2,2,6,6-tetramethyl-4-oxopiperidinyl-1-oxyl to yield 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl 4-formylbenzoate.
It can also be used as a reagent to synthesize acid functionalized mesoporous silica catalyst by the condensation of its aldehyde group with -NH2 of amine functionalized silica.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Sigma-Aldrich

382639

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Highly ordered acid functionalized SBA-15: a novel organocatalyst for the preparation of xanthenes.
Nandi M, et al.
Chemical Communications (Cambridge, England), 47(23), 6677-6679 (2011)
The first two-dimensional barium coordination polymer based on neutral and deprotonated 4-formylbenzoic acid.
Deng ZP, et al.
Applied Organometallic Chemistry, 21(11), 978-982 (2007)
Topochemical studies. VIII. The crystal and molecular sturtures of two polymorphs of 4-formylbenzoic acid.
Haisa MASAO, et al.
Acta Crystallographica Section B, Structural Crystallography and Crystal Chemistry, 32(3), 857-860 (1976)
Elena Sartori et al.
Journal of the American Chemical Society, 129(25), 7785-7792 (2007-06-05)
Interactions between reactive free radicals (r) with stable mononitroxyl radicals (N) and bisnitroxyl radicals (N-X-N) were studied by time-resolved electron paramagnetic resonance (TR-EPR). Reactive spin-polarized free radicals (r#), with non-Boltzmann population of spin states were produced by laser flash photolysis
Yves Meyer et al.
Organic & biomolecular chemistry, 8(8), 1777-1780 (2010-05-08)
This study focuses on the disassembly-behavior of self-immolative pro-fluorescent linkers under physiological conditions and through an enzyme-initiated domino reaction. The targeted linkers are based on para-aminobenzylalcohol (PABA) or hemithioaminal derivatives of para-carboxybenzaldehyde or glyoxilic acid. We found that a fine
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