120-21-8 | 4-(Diethylamino)benzaldehyde

Packsize	Purity	Availability	Price	Discounted Price
5g	95%	in stock	$8.00	$5.00
25g	95%	in stock	$19.00	$13.00
100g	95%	in stock	$34.00	$24.00
500g	95%	in stock	$86.00	$60.00

Description

• Catalog Number: AA33500
• Chemical Name: 4-(Diethylamino)benzaldehyde
• CAS Number: 120-21-8
• Molecular Formula: C11H15NO
• Molecular Weight: 177.24290000000002
• MDL Number: MFCD00003382
• SMILES: CCN(c1ccc(cc1)C=O)CC
• NSC Number: 8782

Computed Properties

• Complexity: 146
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• XLogP3: 2.5

Upstream Synthesis Route

4-(Diethylamino)benzaldehyde, a versatile compound in chemical synthesis, serves as a crucial building block in the creation of various organic molecules. This aldehyde derivative is frequently employed as a reagent in the formation of heterocyclic compounds, such as indoles and pyrazoles, through various organic reactions like the Vilsmeier-Haack reaction and the Fischer indole synthesis. Additionally, 4-(Diethylamino)benzaldehyde is utilized for the synthesis of pharmaceutical intermediates, dyes, and agrochemicals due to its unique chemical properties and reactivity. Its ability to undergo condensation reactions and form Schiff bases makes it a valuable component in the development of diverse chemical entities. Furthermore, its distinctively electron-rich aromatic ring enables it to participate in a range of transformations, making it a key player in the field of organic synthesis.

Literature

• N,N-diethylaminobenzaldehyde (DEAB) as a substrate and mechanism-based inhibitor for human ALDH isoenzymes.

  Chemico-biological interactions 20150605

• Development and validation of an LC-MS/MS method for pharmacokinetic study of methoxyamine in phase I clinical trial.

  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120715

• (E)-4-[4-(Diethyl-amino)-benzyl-idene-ammonio]-benzene-sulfonate.

  Acta crystallographica. Section E, Structure reports online 20120701

• Retinoic acid signaling plays a restrictive role in zebrafish primitive myelopoiesis.

  PloS one 20120101

• Conditional RARα knockout mice reveal acute requirement for retinoic acid and RARα in homeostatic plasticity.

  Frontiers in molecular neuroscience 20120101

• Genomic characterization, phylogeny and gene regulation of g-type lysozyme in sole (Solea senegalensis).

  Fish & shellfish immunology 20111201

• Synthesis, characterization, and spectroscopic investigation of benzoxazole conjugated Schiff bases.

  The journal of physical chemistry. A 20111124

• 2-[4-(Diethyl-amino)-benzyl-idene]malono-nitrile.

  Acta crystallographica. Section E, Structure reports online 20110601

• 2-[(E)-4-(Diethyl-amino)-styr-yl]-1-methyl-pyridinium iodide.

  Acta crystallographica. Section E, Structure reports online 20101001

• 4-Bromo-N-[4-(diethyl-amino)-benzyl-idene]aniline.

  Acta crystallographica. Section E, Structure reports online 20100901

• Cationic schiff base amphiphiles and their metal complexes: Surface and biocidal activities against bacteria and fungi.

  Colloids and surfaces. B, Biointerfaces 20100501

• (E)-1-(4-Chloro-phen-yl)-3-[4-(diethyl-amino)phen-yl]prop-2-en-1-one.

  Acta crystallographica. Section E, Structure reports online 20100201

• 4-Chloro-N-[4-(diethyl-amino)benzyl-idene]aniline.

  Acta crystallographica. Section E, Structure reports online 20100201

• Nolz1 promotes striatal neurogenesis through the regulation of retinoic acid signaling.

  Neural development 20100101

• 4-[4-(Diethyl-amino)benzyl-ideneamino]-4H-1,2,4-triazole.

  Acta crystallographica. Section E, Structure reports online 20080601

• Reactivity of the triple ion and separated ion pair of tris(trimethylsilyl)methyllithium with aldehydes: a RINMR study.

  Journal of the American Chemical Society 20080514

• Synthesis, acidity and antioxidant properties of some novel 3,4-disubstituted-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives.

  Molecules (Basel, Switzerland) 20080119

• Identification of a novel retinoid by small molecule screening with zebrafish embryos.

  PloS one 20080101

• Colorectal cancer stem cells are enriched in xenogeneic tumors following chemotherapy.

  PloS one 20080101

• Complex regulation of cyp26a1 creates a robust retinoic acid gradient in the zebrafish embryo.

  PLoS biology 20071101

• The cdx genes and retinoic acid control the positioning and segmentation of the zebrafish pronephros.

  PLoS genetics 20071001

• 4-(N,N-diethylamino) benzaldehyde thiosemicarbazone in the spectrophotometric determination of palladium.

  Annali di chimica 20071001

• Systemic bud induction and retinoic acid signaling underlie whole body regeneration in the urochordate Botrylloides leachi.

  PLoS biology 20070401

• Vhnf1 acts downstream of Bmp, Fgf, and RA signals to regulate endocrine beta cell development in zebrafish.

  Developmental biology 20070315

• Cyp26 enzymes generate the retinoic acid response pattern necessary for hindbrain development.

  Development (Cambridge, England) 20070101

• A screen for mutations in zebrafish that affect myelin gene expression in Schwann cells and oligodendrocytes.

  Developmental biology 20060901

• A novel cytochrome P450, zebrafish Cyp26D1, is involved in metabolism of all-trans retinoic acid.

  Molecular endocrinology (Baltimore, Md.) 20060701

• Retinoic acid activates myogenesis in vivo through Fgf8 signalling.

  Developmental biology 20060101

• Development and validation of an HPLC-UV method for the analysis of methoxyamine using 4-(diethylamino)benzaldehyde as a derivatizing agent.

  Journal of pharmaceutical and biomedical analysis 20050915

• Retionic acid and its receptors are required for expression of aryl hydrocarbon receptor mRNA and embryonic development of blood vessel and bone in the medaka fish, Oryzias latipes.

  Zoological science 20040501

• Measurement of anti-cancer agent methoxyamine in plasma by tandem mass spectrometry with on-line sample extraction.

  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20031005

• 4-(N,N-dipropylamino)benzaldehyde inhibits the oxidation of all-trans retinal to all-trans retinoic acid by ALDH1A1, but not the differentiation of HL-60 promyelocytic leukemia cells exposed to all-trans retinal.

  BMC pharmacology 20020101

• Measurement of cytokine and adhesion molecule expression in synovial tissue by digital image analysis.

  Annals of the rheumatic diseases 20010301

• De novo expression of transfected human class 1 aldehyde dehydrogenase (ALDH) causes resistance to oxazaphosphorine anti-cancer alkylating agents in hamster V79 cell lines. Elevated class 1 ALDH activity is closely correlated with reduction in DNA interstrand cross-linking and lethality.

  The Journal of biological chemistry 19960517