157027-34-4

Basic information

• Product Name: 2,4-dichloro-3-morpholin-4-ylquinoline
• CAS NO: 157027-34-4
• Molecular Formula: C₁₃H₁₂Cl₂N₂O
• Molecular Weight: 283.1532
• Mol File: 157027-34-4.mol

Chemical Properties

• Boiling Point: 422.3°C at 760 mmHg
• Flash Point: 209.2°C
• Density: 1.388g/cm³
• Vapor Pressure: 2.43E-07mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: 2,4-dichloro-3-morpholin-4-ylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dichloro-3-morpholin-4-ylquinoline(157027-34-4)
• EPA Substance Registry System: 2,4-dichloro-3-morpholin-4-ylquinoline(157027-34-4)

Safety Data

• Hazardous Substances Data: 157027-34-4(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
2,4-dichloro-3-morpholin-4-ylquinoline is utilized as a pesticide and herbicide for its effectiveness in managing a broad range of weeds. Its application in agriculture is aimed at enhancing crop yield by reducing the competition from unwanted plant species, thereby ensuring healthier and more productive crops.
However, it is crucial to handle 2,4-dichloro-3-morpholin-4-ylquinoline with care due to its potential harmful effects on both humans and the environment if not used properly. This underscores the need for responsible application and adherence to safety guidelines to mitigate any adverse impacts.

Upstream product

• 152208-21-4 2-(Iodacetylamino)benzoesaeure-ethylester 
• 101496-75-7 N-<(morpholin-4-yl)methylcarbonyl>anthranilic acid ethyl ester 
• 14933-27-8 4-hydroxy-3-morpholin-4-yl-2(1H)-quinolone 

Downstream Products

• 157027-54-8 4-chloro-3-morpholino-2-(triphenylphosphoranylideneamino)-quinoline 

Relevant articles and documents

3-amino-2(1H)-quinolones by cyclization of N-acylated anthranilic acid derivatives

Reaction of secondary amines with the N-(iodoacetyl)anthranilic acid derivatives, 2-(iodoacetylamino)acetophenone and 2-(iodoacetylamino)benzophenone yields 3-amino-2(1H)-quinolones in two steps. Analogously heterocondensed 5-amino-6(7H)-pyrazolo[5,4-b]pyridoues were prepared. Hydroxyquinolines were subjected to Cl/OH exchange to give chloroquinolines, which are convenient for consecutive reactions.

Regioselective Azidation of 2,4-Dichloroquinolines

Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazoloquinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chlorotetrazoloquinolines (5g-i).When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazoloquinolines (5a-i) are obtained.Structural assignments of 3 and 5 have been carried out by 13C-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9).It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.