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
• Uses: 4-(Diethylamino)salicylaldehyde is usually used in the synthesis of Schiff-base ligand by monocondensation with diaminomaleonitrile. 4-(Diethylamino)salicylaldehyde was used in the synthesis of Schiff-base ligand by monocondensation with diaminomaleonitrile.

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:

3,3'-carbonyl-bis(7-diethylaminocoumarin)

7-diethylamino-3-thenoylcoumarin

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

• 1、 Dalapati, Sasanka,Jana, Sankar,Guchhait, Nikhil. "Colorimetric "Naked-eye" highly selective detection of Cu(II) ion by a simple chemosensor: An experimental and theoretical modeling". . p. 279 - 281. Retrieved 2011.
• 2、 Mathivanan, Moorthy,Tharmalingam, Balamurugan,Lin, Chia-Her,Pandiyan, Baskaran Vijaya,Thiagarajan, Viruthachalam,Murugesapandian, Balasubramanian. "ESIPT-active multi-color aggregation-induced emission features of triphenylamine-salicylaldehyde-based unsymmetrical azine family". . p. 213 - 228. Retrieved 2019.
• 3、 Yue, Yongkang,Huo, Fangjun,Li, Xiaoqi,Wen, Ying,Yi, Tao,Salamanca, James,Escobedo, Jorge O.,Strongin, Robert M.,Yin, Caixia. "PH-dependent fluorescent probe that can be tuned for cysteine or homocysteine". . p. 82 - 85. Retrieved 2017.
• 4、 Huang, You,Li, Xiaohu. "Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles". supporting information. p. 9934 - 9937. Retrieved 2021/10/12.
• 5、 Zhang, Han,Xia, Xiang,Zhao, Hong,Zhang, Guo-Ning,Jiang, Dao-Yong,Xue, Xing-Ying,Zhang, Jiao. "A near-infrared fluorescent probe based on SNAr reaction for H2S/GSH detection in living cells and zebrafish". . p. 183 - 189. Retrieved 2018/12/11.