o-Phthalaldehyde

• CAS: 643-79-8
• Catalog Number: ACM643798
• Category: Main Products
• Molecular Weight: 134.13
• Molecular Formula: C8H6O2
• Appearance: Solid

Case Study

Application of o-Phthalaldehyde in Advanced Hydrogel Cross-Linking Technology

Zhang, Zhen, et al. National Science Review 8.4 (2021): nwaa128.

In this work, o-Phthalaldehyde (OPA) served as a highly efficient, catalyst-free cross-linking reagent for construction of covalently cross-linked hydrogels by condensation with N-nucleophiles (primary amines, hydrazides, aminooxy groups). When used to cap four-arm PEG or to functionalize natural polymers/proteins, OPA enables superfast gelation under physiological conditions, produces networks with higher mechanical strength and lower critical gelation concentrations than benzaldehyde-based alternatives, and allows facile incorporation of bioactive amines into the gel network.
Reaction mechanism & kinetics: Small-molecule model studies indicate the defining chemistry is the fast formation of phthalimidine or isoindole (bis)hemiaminal species. The second-order rate constant measured for OPA reacting with methylamine was reported as 4.3 /M/s, a reactivity that is ≈3,000× and ≈200× higher than the rates reported for acylhydrazone and oxime formation from benzaldehyde, respectively, and comparable to many cycloaddition "click" reactions. This intrinsic reactivity explains the exceptionally rapid gelation observed with OPA-based cross-linking.
Hydrogel formulation & scope: OPA chemistry was demonstrated by mixing OPA-capped four-arm PEG (4aPEG-OPA) with complementary N-nucleophile-terminated 4aPEG; analogous OPA cross-linking was also applied to naturally derived polysaccharides, proteins and synthetic polymers. Because the reaction tolerates aqueous/physiological conditions and requires no catalyst, a wide variety of polymer backbones and biomolecules can be converted into covalently cross-linked hydrogels using the same core chemistry.

o-Phthalaldehyde as a Highly Effective Catalyst for Chemoselective Hydrolysis of Organophosphorus Compounds

Zhang, Yongbin, et al. Sensors and Actuators B: Chemical 273 (2018): 944-950.

This study reported that o-phthalaldehyde (OPA) functions as an efficient, nonmetallic catalyst for hydrolysing a broad set of organophosphorus substrates that contain a P(=O)-NH motif (phosphinic amides and phosphoramidates). Under relatively mild conditions OPA promotes electrophilic activation via reversible covalent interaction with the nitrogen atom, enabling high-yield conversions for many substrates and, in mixed-functionality substrates, chemoselective cleavage of P(=O)-N bonds in the presence of P(=O)-OR groups.
Broad Substrate Scope: Diphenylphosphinic amides with N-alkyl and N-aryl substituents (N-phenylethyl, N-benzyl, N-phenyl, N-methyl, N-propyl, N-isopropyl, N-cyclopropyl) were hydrolysed efficiently, with isolated yields commonly in the mid-80s to high-90s percent range. Substrates bearing additional functional groups (alkene, alkyne, free alcohol) were tolerated and converted in good yields (75-97%). Simple phosphinic amides and α-amino-ester-derived phosphinic amides also underwent hydrolysis successfully (yields 61-98%).
For phosphoramidates (containing both P-N and P-O bonds) OPA effected chemoselective hydrolysis of the P-N bond in many cases: a range of N-alkyl phosphoramidates were converted in high yields (85-96%), whereas less nucleophilic N-aryl examples reacted less efficiently (34% for one N-phenyl substrate). Simple diphenyl phosphoramidate and heteroaryl derivatives were also converted in moderate to high yields (e.g., 77-92%).

Custom Q&A

What is the molecular formula of o-Phthalaldehyde?

The molecular formula of o-Phthalaldehyde is C6H4(CHO)2.

What are some synonyms of o-Phthalaldehyde?

Some synonyms of o-Phthalaldehyde include o-Phthaldialdehyde, Benzene-1,2-dicarboxaldehyde, Phthaldialdehyde, and Phthalic aldehyde, among others.

Is o-Phthalaldehyde flammable?

Yes, o-Phthalaldehyde is flammable.

What are some hazards associated with o-Phthalaldehyde?

Some hazards associated with o-Phthalaldehyde include being corrosive, acute toxic, irritant, and a health and environmental hazard.

What is the IUPAC name of o-Phthalaldehyde?

The IUPAC name of o-Phthalaldehyde is phthalaldehyde.

What is the InChIKey of o-Phthalaldehyde?

The InChIKey of o-Phthalaldehyde is ZWLUXSQADUDCSB-UHFFFAOYSA-N.

What is the computed descriptor for the canonical SMILES of o-Phthalaldehyde?

The computed descriptor for the canonical SMILES of o-Phthalaldehyde is C1=CC=C(C(=C1)C=O)C=O.

What is the CAS number of o-Phthalaldehyde?

The CAS number of o-Phthalaldehyde is 643-79-8.

What is the role of o-Phthalaldehyde?

o-Phthalaldehyde has a role as an epitope.

What is the create date and modify date of the reference?

The create date of the reference is 2005-03-25 and the modify date is 2023-08-26.