4-(Diethylamino)salicylaldehyde

Base Information

• Chemical Name: 4-(Diethylamino)salicylaldehyde
• CAS No.: 17754-90-4
• Deprecated CAS: 1436710-40-5
• Molecular Formula: C11H15NO2
• Molecular Weight: 193.246
• Hs Code.: 29225090
• European Community (EC) Number: 241-745-3
• UNII: OU5NFU4681
• DSSTox Substance ID: DTXSID5022271
• Nikkaji Number: J30.756D
• Wikidata: Q27285847
• ChEMBL ID: CHEMBL3561306
• Mol file: 17754-90-4.mol

Synonyms:4-(diethylamino)-2-hydroxybenzaldehyde

Chemical Property of 4-(Diethylamino)salicylaldehyde

Chemical Property:

• Appearance/Colour: beige to purple crystalline powder
• Vapor Pressure: 0.0001mmHg at 25°C
• Melting Point: 60-62 °C(lit.)
• Refractive Index: 1.601
• Boiling Point: 328.288 °C at 760 mmHg
• PKA: 8.29±0.10(Predicted)
• Flash Point: 152.343 °C
• PSA: 40.54000
• Density: 1.133 g/cm³
• LogP: 2.05090
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 180

Purity/Quality:

99% ^*data from raw suppliers

6- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C1=CC(=C(C=C1)C=O)O
• General Description: 4-(Diethylamino)salicylaldehyde is a key precursor in the synthesis of Schiff base ligands, particularly for investigating nonlinear optical (NLO) properties in coordination chemistry. It is commonly used in condensation reactions with amines, such as 4-nitroaniline or diaminomaleonitrile, to form ligands that coordinate with transition metals like nickel(II), copper(II), and cobalt(II). These complexes are studied for their potential applications in optical data storage and telecommunications due to their enhanced NLO responses and thermal stability. The ligand's structure, featuring a diethylamino donor group and a hydroxyl-aldehyde moiety, facilitates the formation of stable metal complexes with tunable electronic and optical properties.

Technology Process of 4-(Diethylamino)salicylaldehyde

There total 9 articles about 4-(Diethylamino)salicylaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 3-diethylaminophenol (91-68-9) → 4-(Diethylamino)salicylaldehyde (17754-90-4)

Guidance literature:

With trichlorophosphate; at 75 ℃; for 2h; Temperature; Cooling with ice;

Reference yield: 95.0%

2-(benzyloxy)-4-(diethylamino)benzaldehyde (93109-27-4) → 4-(Diethylamino)salicylaldehyde (17754-90-4)

Guidance literature:

With palladium diacetate; sodium hydride; In N,N-dimethyl acetamide; at 25 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acscatal.8b00185

Reference yield:

(E)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)-5-methoxybenzenesulfonic acid → 4-(Diethylamino)salicylaldehyde (17754-90-4) + 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Guidance literature:

With sodium hypochlorite; In aq. phosphate buffer; N,N-dimethyl-formamide; pH=7.4;

DOI:10.1007/s12039-019-1617-6

upstream raw materials:

N,N-dimethyl-formamide

3-diethylaminophenol

2-acetoxy-5-bromo-4-(diethylamino)benzaldehyde

5-(diethylamino)-2-formylphenyl acetate

Downstream raw materials:

7-diethylamino-3-thenoylcoumarin

7-Diethylamino-4-[(E)-2-(4-diethylamino-2-hydroxy-phenyl)-vinyl]-chromen-2-one

7-diethylamino-3-(4-dimethylaminobenzoyl)coumarin

7-Diethylamino-3-{[1-(4-diethylamino-2-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-4-methyl-chromen-2-one

Refernces

Synthesis, crystal structures, and molecular hyperpolarizabilities of a new Schiff base ligand, and its copper(II), nickel(II), and cobalt(II) metal complexes

10.1016/j.ica.2004.03.004

The study focuses on the synthesis, crystal structures, and molecular hyperpolarizabilities of a new Schiff base ligand (HL) derived from the condensation of 4-(diethylamino)salicylaldehyde with 4-nitroaniline, and its metal complexes with nickel(II), copper(II), and cobalt(II). The purpose of these chemicals is to investigate their quadratic nonlinear optical (NLO) properties, which are crucial for applications in fields like telecommunications and optical data storage. The Schiff base ligand and its metal complexes were analyzed for their crystal structures, thermal stability, and NLO responses, with the aim of understanding how the introduction of a metal center can enhance the NLO response and improve thermal stability. The study found that while the nickel(II) and copper(II) complexes were centrosymmetric and thus had vanishing hyperpolarizabilities, the cobalt(II) complex exhibited a pseudo-tetrahedral structure, leading to an enhancement of the NLO response and an increase in thermal stability.

Synthesis, crystal structures, and nonlinear optical (nlo) properties of new schiff-base nickel(ll) complexes. toward a new type of molecular switch?

10.1021/ic048578n

The study focuses on the synthesis, crystal structures, and nonlinear optical (NLO) properties of new Schiff-base nickel(II) complexes. The main chemical used is an H2L Schiff-base ligand, obtained from the monocondensation of diaminomaleonitrile and 4-(diethylamino)salicylaldehyde, along with four related nickel(II) complexes formulated as [Ni(L)(L′)], where L′ represents various ligands such as MePhCHNH2, iPrNH2, Py, and PPh3. The purpose of these chemicals is to investigate the formation of a unique nickel amido bond through deprotonation and to explore the potential of these complexes as molecular switches in nonlinear optics due to their NLO properties. The study employs techniques like electric-field-induced second-harmonic (EFISH) to measure quadratic hyperpolarizability and ZINDO/SCI quantum chemical calculations to understand the orientation of hyperpolarizability in relation to laser wavelength, aiming to identify a new type of molecular switch based on the rotation of the NLO response rather than a reduction in its magnitude.