Isophthalaldehyde

Isophthalaldehyde
Names
	Other names 1,3-Benzenedialdehyde, 1,3-Diformylbenzene
Identifiers
CAS Number	626-19-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2289228;
ChemSpider	32002;
ECHA InfoCard	100.009.942
EC Number	210-935-8;
PubChem CID	34777;
UNII	LU162B2N9X;
CompTox Dashboard (EPA)	DTXSID30870718 ;
	InChI InChI=1S/C8H6O2/c9-5-7-2-1-3-8(4-7)6-10/h1-6H Key: IZALUMVGBVKPJD-UHFFFAOYSA-N;
	SMILES C1=CC(=CC(=C1)C=O)C=O;
Properties
Chemical formula	C8H6O2
Molar mass	134.134 g·mol−1
Appearance	white
Density	1.395 g/cm3
Melting point	89.5 °C (193.1 °F; 362.6 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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]

Related compounds

References

^ 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.
^ "Isophthalaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 3 February 2022.
^ Ackerman, J. H.; Surrey, A. R. (1967). "Isophthalaldehyde". Organic Syntheses. 47: 76. doi:10.15227/orgsyn.047.0076.
^ 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.
^ 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.
^ 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.

[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.

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