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Sigma-Aldrich

3-Formylbenzoic acid

97%

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Synonym(s):
3-Carboxybenzaldehyde, Isophthalaldehydic acid
Linear Formula:
HO2CC6H4CHO
CAS Number:
Molecular Weight:
150.13
Beilstein/REAXYS Number:
2206413
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

powder

mp

173-175 °C (lit.)

solubility

methanol: soluble 100 mg/mL, clear to slightly hazy, colorless to very faintly brown(lit.)

SMILES string

[H]C(=O)c1cccc(c1)C(O)=O

InChI

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

InChI key

UHDNUPHSDMOGCR-UHFFFAOYSA-N

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General description

3-Formylbenzoic acid is a polar aromatic aldehyde used in the synthesis of 3-hydroxymethylbenzoic acid via reduction.

Application

3-Formylbenzoic acid was used in the synthesis of:
  • bicyclic cis-2-azetidinone derivatives via Ugi 4-centre 3-component reaction
  • porphyrin capped with a steroidal superstructure bearing convergent hydroxy groups
  • 3-[(4-amino-1,2-dihydro-1-oxo-2-phenyl-1,2,4-triazolo[4,3-a]quinoxalin-6-yl)amino]methylbenzoic acid

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Synthesis of Alicyclic-lactams via the Ugi Reaction on a Solid Support.
Gedey S, et al.
Letters in Organic Chemistry, 1(3), 215-220 (2004)
Vittoria Colotta et al.
Bioorganic & medicinal chemistry, 11(24), 5509-5518 (2003-12-04)
In previous papers (Colotta, V. et al. Arch. Pharm. Pharm. Med. Chem. 1999, 332, 39. Colotta, V. et al. J. Med. Chem. 2000, 43, 1158) we reported the synthesis and binding affinity at bovine (b) A(1) and A(2A) and human
Synthesis, binding properties and self-functionalization of a steroid-capped porphyrin.
Richard P and Jeremy KM.
Journal of the Chemical Society. Chemical Communications, 8, 574-577 (1991)
Suhman Chung et al.
Nature chemical biology, 5(6), 407-413 (2009-04-28)
The linking together of molecular fragments that bind to adjacent sites on an enzyme can lead to high-affinity inhibitors. Ideally, this strategy would use linkers that do not perturb the optimal binding geometries of the fragments and do not have
Rational substrate and enzyme engineering of transketolase for aromatics
Payongsri, et al.
Organic & Biomolecular Chemistry, 10, 9021-9029 (2012)

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