4-(Dimethylamino)benzaldehyde

• CAS: 100-10-7
• Catalog Number: ACM100107
• Category: Main Products
• Molecular Weight: 149.19
• Molecular Formula: C9H11NO
• Synonyms: 4-(Dimethylamino)benzaldehyde; para-dimethylaminobenzaldehyde; Ehrlichs; reagensehrlichovo; N,N-dimethyl-p-aminobenzaldehyde; EHRLICHS REAGENT; p-Dimethylaminobenzaldehyde; N,N-dimethyl-4-aminobenzaldehyde; HYDRAZINE-REAGENT; p-DAB; 4-N,N-dimethylaminobenzaldehyde; EHRICHS REAGENT; p-N,N-dimethylaminobenzaldehyde; ERLICHS REAGENT
• IUPAC Name: 4-(dimethylamino)benzaldehyde
• Canonical SMILES: CN(C)C1=CC=C(C=C1)C=O
• InChI Key: BGNGWHSBYQYVRX-UHFFFAOYSA-N
• Boiling Point: 176-177ºC (17 mmHg)
• Melting Point: 70-75ºC
• Flash Point: 164ºC
• Density: 1.072 g/cm³
• Appearance: solid
• EC Number: 202-819-0
• Exact Mass: 149.08400
• Hazard Statements: Xn:Harmful
• Packing Group: I; II; III
• Safety Description: S61
• Stability: Stable, but light sensitive. Incompatible with bases, strong oxidizing agents.
• WGK Germany: 1

Case Study

Synthesis of Schiff Bases Based on 4-(Dimethylamino)Benzaldehyde and Their Complexes

Latif M A, et al. Russian Journal of General Chemistry, 2019, 89(6), 1197-1201.

Schiff bases containing nitrogen and sulfur donor chains can be prepared by the condensation reaction of 4-(dimethylamino)benzaldehyde with S-benzyl dithiocarbamate (SBDTC). The obtained Schiff base can be further coordinated with Ni(II), Cu(II) and Zn(II) to obtain the corresponding metal complexes.
· Synthesis of Benzyl N'-(4-dimethylaminobenzylidene)hydrazinecarbodithioate (SB)
A solution of 1.98 g (10 mmol) of SBDTC in 50‒60 mL of hot absolute ethanol was added to a solution of the equimolar amount of 4-(dimethylamino)benzaldehyde in 20 mL of the same solvent. The mixture was refluxed for 40 min. The yellow precipitate that formed was separated and dried in vacuo over anhydrous CaCl2, yield 68%.
· Synthesis of metal complexes of the Schiff base
A solution of 0.329 g (1 mmol) of SB in 70 mL of hot absolute ethanol was added to a solution of the metal salt hydrate [Ni(NO3)2·6H2O] (0.145 g, 0.5 mmol ), [Cu(NO3)2·3H2O] (0.121 g, 0.5 mmol), or [Zn(NO3)2·6H2O] (0.148 g, 0.5 mmol) in 20 mL of absolute ethanol. The mixture was refluxed for 40 min and then cooled. The precipitate that formed was filtered off, washed with hot ethanol, and dried in vacuo over anhydrous CaCl2.

Synthesis and Biological Activity of Schiff Base Metal Complexes of 4-Dimethylaminobenzaldehyde Derivatives

Ali A, et al. Inorganic Chemistry Communications, 2022, 145, 109903.

New Schiff bases can be formed by condensation of 4-dimethylaminobenzaldehyde and benzamide in a 1:1 M ratio. Schiff base has strong biological activities, including antifungal, anticancer, antibacterial and other activities. These Schiff bases can further improve catalytic activity by forming complexes with metals, such as transition metals (Ni, Co, Zn, Pb). Here are just a few examples:
· Morad et al. used the condensation of aldehydes and amine derivatives to form new Schiff base ligands and explored their antibacterial activity.
· Elzahany et al. used 2-formyl indole to synthesize N-aminorhodanine and metal complexes of salicylaldehyde and Schiff base. They also studied its antibacterial activity against a variety of bacteria including Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus.
· Some other Schiff bases are obtained by the condensation of o-vanillin and diaminopyridine. Some Schiff bases exhibit antifungal, antibacterial and other biological activities.

4-(Dimethylamino)benzaldehyde as a Hydrogen Bond Acceptor in Deep Eutectic Solvent Synthesis and Urea Derivatization for Analytical Applications

Shishov A, et al. Journal of Molecular Liquids, 2022, 353, 118820.

In a novel study, 4-(dimethylamino)benzaldehyde was successfully employed in the synthesis of a deep eutectic solvents (DES), using thymol as the hydrogen bond donor, under controlled conditions (40°C). The resulting DES exhibited stability in aqueous environments and functioned as a hydrophobic extractant, making it highly suited for microextraction procedures.
The primary application of 4-(dimethylamino)benzaldehyde in this context is its involvement in the derivatization of urea, where it reacts with urea to form a Schiff base derivative. This colored complex enhances the detection of urea, streamlining its extraction into the DES phase for subsequent analysis. The method not only reduces sample pretreatment time but also simplifies the analysis process, with a remarkable detection limit of 0.1 mg L⁻¹ for human urine and 2 mg kg⁻¹ for powdered milk samples. This innovative procedure, leveraging 4-(dimethylamino)benzaldehyde, also demonstrates excellent reproducibility (RSD values < 7%) and notable enrichment factors (24 for urine and 23 for milk), marking it as an efficient approach for the determination of urea in real-world samples.

4-(Dimethylamino)benzaldehyde as a Dopant in Triglycine Sulphate Crystals for Modified Crystal Growth and Morphology

Rai C, et al. Physica B: Condensed Matter, 2009, 404(21), 3886-3889.

In a recent study, single crystals of triglycine sulphate (TGS) were doped with 1 mol% of 4-(dimethylamino)benzaldehyde (DB), grown via the slow evaporation technique from an aqueous solution at ambient temperature. The dopant influenced both the growth rate and the morphology of the resulting crystals, with doped TGS crystals exhibiting a slower growth rate and slightly modified morphology compared to pure TGS crystals.
The doping of TGS with 4-(dimethylamino)benzaldehyde led to noticeable alterations in the crystal structure, particularly along the a and b axes, likely due to the incorporation of the DB molecules into the crystal lattice. The doped crystals also displayed a faint yellowish hue, distinguishing them from the pure TGS crystals. This modification of the crystal's physical characteristics has potential implications for applications in nonlinear optical devices, as TGS is widely utilized in such fields due to its pyroelectric and ferroelectric properties.

Custom Reviews

Semptember 11, 2022

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Custom Q&A

What is molecular formula of 4-(dimethylamino)benzaldehyde?

C9H11NO

What is CCDC Number of 4-(dimethylamino)benzaldehyde?

696471

What is IUPAC Name of 4-(dimethylamino)benzaldehyde?

4-(dimethylamino)benzaldehyde

What is InChI of 4-(dimethylamino)benzaldehyde?

InChI=1S/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3

What is InChIKey of 4-(dimethylamino)benzaldehyde?

BGNGWHSBYQYVRX-UHFFFAOYSA-N