Isophthalaldehyde

Isophthalaldehyde
Names
Other names
1,3-Benzenedialdehyde, 1,3-Diformylbenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.009.942 Edit this at Wikidata
EC Number
  • 210-935-8
UNII
  • InChI=1S/C8H6O2/c9-5-7-2-1-3-8(4-7)6-10/h1-6H
    Key: IZALUMVGBVKPJD-UHFFFAOYSA-N
  • C1=CC(=CC(=C1)C=O)C=O
Properties
C8H6O2
Molar mass 134.134 g·mol−1
Appearance white
Density 1.395 g/cm3[1]
Melting point 89.5 °C (193.1 °F; 362.6 K)
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isophthalaldehyde is an organic compound with the formula C6H4(CHO)2. It is one of three isomers of benzene dicarbaldehyde, a reduced analog of phthalic acid. It is a colorless solid, although commercial samples often appear yellowish. One preparation entails the Sommelet reaction of α,α'-diamino-ortho-xylene.[3]

Reactions and use

Like many benzaldehydes, isophthalaldehyde forms a variety of Schiff base derivatives. Being bifunctional (having two formyl groups), isophthalaldehyde allows the formation of polymers or covalent organic frameworks upon reaction with di- or triamines.[4] [5] They also find use in metal coordination complexes.[6]

References

  1. ^ Britton, Doyle (2002). "O- andm-Benzenedicarbaldehyde". Acta Crystallographica Section C Crystal Structure Communications. 58 (11): o637 – o639. doi:10.1107/S0108270102015597. PMID 12415166. S2CID 7685455.
  2. ^ "Isophthalaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 3 February 2022.
  3. ^ Ackerman, J. H.; Surrey, A. R. (1967). "Isophthalaldehyde". Organic Syntheses. 47: 76. doi:10.15227/orgsyn.047.0076.
  4. ^ Schwab, Matthias Georg; Fassbender, Birgit; Spiess, Hans Wolfgang; Thomas, Arne; Feng, Xinliang; Müllen, Klaus (2009). "Catalyst-free Preparation of Melamine-Based Microporous Polymer Networks through Schiff Base Chemistry". J. Am. Chem. Soc. 131 (21): 7216–7217. doi:10.1021/ja902116f. PMID 19469570.
  5. ^ Schoustra, Sybren K.; Smulders, Maarten M. J. (2023). "Metal Coordination in Polyimine Covalent Adaptable Networks for Tunable Material Properties and Enhanced Creep Resistance". Macromolecular Rapid Communications. 44 (5): 2200790. doi:10.1002/marc.202200790. PMID 36629864. S2CID 255593988.
  6. ^ Nasr, G.; Macron, T.; Gilles, A.; Mouline, Z.; Barboiu, M. (2012). "Metallodynameric membranes – toward the constitutional transport of gases". Chemical Communications. 48 (54): 6827–6829. doi:10.1039/C2CC32656F.