14371-13-2

Basic information

• Product Name: N-(Dimethylamino)-4-methoxybenzenemethanimine
• Synonyms: 4-Methoxybenzaldehyde dimethyl hydrazone;N-(Dimethylamino)-4-methoxybenzenemethanimine;p-Anisaldehyde dimethylhydrazone
• CAS NO: 14371-13-2
• Molecular Formula: C₁₀H₁₄N₂O
• Molecular Weight: 0
• Mol File: 14371-13-2.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 295.2°C at 760 mmHg
• Flash Point: 132.3°C
• Appearance: /
• Density: 0.96g/cm³
• Vapor Pressure: 0.00155mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: N-(Dimethylamino)-4-methoxybenzenemethanimine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Dimethylamino)-4-methoxybenzenemethanimine(14371-13-2)
• EPA Substance Registry System: N-(Dimethylamino)-4-methoxybenzenemethanimine(14371-13-2)

Safety Data

• Hazardous Substances Data: 14371-13-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 4100, 1966 DOI: 10.1021/jo01350a053

InChI:InChI=1/C10H14N2O/c1-12(2)11-8-9-4-6-10(13-3)7-5-9/h4-8H,1-3H3

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 57-14-7 N,N-Dimethylhydrazine 
• 123-11-5 4-methoxy-benzaldehyde 
• 95-68-1 2,4-Xylidine 
• 62-53-3 aniline 
• 104-94-9 4-methoxy-aniline 
• 106-49-0 p-toluidine 
• 66064-57-1 (E)-1,1-dimethyl-2-(2-methylallylidene)hydrazine 
• 836-41-9 p-methoxybenzylidene-phenylamine 
• 53384-70-6 N-(4-methoxy-benzylidene)-2,4-dimethyl-aniline 
• 1749-08-2 N-(4-methoxy benzylidene)-4-methoxyaniline 
• 3246-78-4 N-(4-methoxybenzylidene)-4-methylaniline 
• 70978-37-9 1-(azidomethyl)-4-methoxybenzene 

Downstream Products

• 1314779-65-1 2-(dimethylamino)-4'-methoxybenzophenone 
• 1362849-67-9 (CH₃)4C₂O₂BC₆H₃(OCH₃)CHNN(CH₃)2 
• 1360607-18-6 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone 
• 51093-44-8 3‐(4‐methoxyphenyl)‐1‐methyl‐1H‐indazole 
• 129249-38-3 2,2,2-Trifluoro-1-[5-(4-methoxy-phenyl)-3-methyl-6-trifluoromethyl-2,3-dihydro-[1,3,4]oxadiazin-4-yl]-ethanone 
• 343948-47-0 (Dimethyl-hydrazono)-(4-methoxy-phenyl)-acetaldehyde 
• 111269-66-0 3,3,3-Trifluoro-1-(4-methoxy-phenyl)-propane-1,2-dione 
• 121194-35-2 3,3,3-trifluoro-1-(4-methoxyphenyl)propan-1-one 
• 220248-48-6 1,1,1-trifluoro-3-hydrazono-3-(4-methoxy-phenyl)-propan-2-one 
• 161643-65-8 3,3,3-trifluoro-2,2-dihydroxy-1-(4-methoxy-phenyl)-propan-1-one 
• 3424-93-9 4-methoxyphenylacetamide 
• 874-90-8 4-methoxybenzonitrile 
• 100-09-4 4-methoxybenzoic acid 
• 256934-10-8 1-(dimethylamino)-3-methoxy-2-(4-methoxyphenyl)-2,5-dihydropyrrole 

Relevant articles and documents

Perfluoroalkylation of Aryl-N,N-dimethyl Hydrazones Using Hypervalent Iodine(III) Reagents or Perfluoroalkyl Iodides

Radical trifluoromethylation of aryl N,N-dimethyl hydrazones using TBAI as an initiator and Togni's reagent as a trifluoromethyl radical source is described. Cascades proceed via electron-catalysis; this approach is generally more applicable to hydrazone perfluoroalkylation using perfluoroalkyl iodides as the radical precursors in combination with a base under visible-light initiation.

New types of reactivity of α,β-unsaturated N,N- dimethylhydrazones: Chemodivergent diastereoselective synthesis of functionalized tetrahydroquinolines and hexahydropyrrolo[3,2-b]indoles

The indium trichloride-catalyzed reaction between aromatic imines and α,β-unsaturated N,N-dimethylhydrazones in acetonitrile afforded 1,2,3,4-tetrahydroquinolines bearing a hydrazone function at C4 through a one-pot diastereoselective domino process that involves the formation of two C-C bonds and the controlled generation of two stereocenters, one of which is quaternary. This reaction constitutes the first example of an α,β-unsaturated dimethylhydrazone that behaves as a dienophile in a hetero Diels-Alder reaction. The related reaction between anilines, aromatic aldehydes, and methacrolein dimethylhydrazone in CHCl3 with BF 3·Et2O as catalyst afforded polysubstituted 1,2,3,3a,4,8b-hexahydropyrrolo[3,2-b]indoles as major products through a fully diastereoselective ABB′C four-component domino process that generates two cycles, three stereocenters, two C-C bonds, and two C-N bonds in a single operation. Copyright

Synthesis of o -(dimethylamino)aryl ketones, acridones, acridinium salts, and 1 H -indazoles by the reaction of hydrazones and arynes

A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.