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T2207

Sigma-Aldrich

Terephthalaldehyde

ReagentPlus®, 99%

Synonym(s):

Benzene-1,4-dicarboxaldehyde, Terephthaldicarboxaldehyde

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About This Item

Linear Formula:
C6H4(CHO)2
CAS Number:
623-27-8
Molecular Weight:
134.13
Beilstein:
385863
EC Number:
210-784-8
MDL number:
MFCD00006949
UNSPSC Code:
12352100
PubChem Substance ID:
57654660
NACRES:
NA.22

product line

ReagentPlus®

Assay

99%

bp

245-248 °C (lit.)

mp

114-116 °C (lit.)

SMILES string

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

InChI

1S/C8H6O2/c9-5-7-1-2-8(6-10)4-3-7/h1-6H

InChI key

KUCOHFSKRZZVRO-UHFFFAOYSA-N

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Application

Terephthalaldehyde can be used as a starting material for:
  • The synthesis of fused bis-benzoquinoline derivatives on reacting with arylamines and cyclic ketones through one pot three component reaction.
  • The photochemical synthesis of 5,10-disubstituted[5]helicenes by reacting with benzyl cyanide via Knoevenagel reaction.
  • The synthesis of a nitronyl nitroxide (NIT) radical with a pyrimidiniumolate unit, which are useful precursors for building molecular magnets.

Legal Information

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

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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Facile photochemical synthesis of 5, 10-disubstituted [5] Helicenes by removing molecular orbital degeneracy
Ito N, et al.
Organic Letters, 16(9), 2502-2505 (2014)
Camphorsulfonic acid catalyzed one-pot three-component reaction for the synthesis of fused quinoline and benzoquinoline derivatives
Gattu R, et al.
The Journal of Organic Chemistry, 82(23), 12416-12429 (2017)
Synthesis of dipolar nitronyl nitroxides
Greve S, et al.
Organic Letters, 2(15), 2269-2270 (2000)
Abel T Demissie et al.
Journal of the American Chemical Society, 137(27), 8819-8828 (2015-06-23)
We report the systematic characterization of anisotropic, π-conjugated oligophenyleneimine (OPI) films synthesized using stepwise imine condensation, or "click" chemistry. Film synthesis began with a self-assembled monolayer (SAM) of 4-formylthiophenol or 4-aminothiophenol on Au, followed by repetitive, alternate addition of terephthalaldehyde

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