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.

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