4637-59-6

Basic information

• Product Name: 4-Chloroquinoline 1-oxide
• Synonyms: 4-Chloroquinoline 1-oxide
• CAS NO: 4637-59-6
• Molecular Formula: C₉H₆ClNO
• Molecular Weight: 179.6
• Mol File: 4637-59-6.mol
• Article Data: 26

Chemical Properties

• Melting Point: 133-134 °C
• Boiling Point: 336.0±34.0 °C(Predicted)
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• PKA: 0.72±0.10(Predicted)
• CAS DataBase Reference: 4-Chloroquinoline 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloroquinoline 1-oxide(4637-59-6)
• EPA Substance Registry System: 4-Chloroquinoline 1-oxide(4637-59-6)

Safety Data

• Hazardous Substances Data: 4637-59-6(Hazardous Substances Data)

Upstream product

• 611-35-8 4-chloroquinoline 
• 2508-86-3 4-aminoquinoline 1-oxide 
• 56-57-5 4-nitroquinoline-N-oxide 
• 1613-37-2 Quinoline N-oxide 
• 91-22-5 quinoline 

Downstream Products

• 14547-98-9 4-methoxyquinoline-N-oxide 
• 69619-12-1 4-phenoxyquinoline N-oxide 
• 115913-62-7 4-(phenylthio)quinoline 1-oxide 
• 157563-21-8 4-(4-nitro-phenylsulfanyl)-quinoline-1-oxide 
• 4552-43-6 4-chloroquinoline-2-carbonitrile 
• 611-35-8 4-chloroquinoline 
• 68207-88-5 2-phenyl-furo[3,2-c]quinoline-3-carboxylic acid ethyl ester 
• 74421-81-1 4-benzylquinoline 1-oxide 
• 76278-25-6 4-(4-Chloro-quinolin-2-yl)-2-phenyl-4H-oxazol-5-one 
• 75003-52-0 5-(4-Chloro-quinolin-2-yl)-3-phenyl-2-thioxo-thiazolidin-4-one 
• 110036-04-9 4-(cyanophenylthio)methylquinoline 1-oxide 
• 110036-00-5 4-chloro-2-phenylsulfonylmethylquinoline 1-oxide 
• 139366-52-2 2-phenyl-3-mesyl-furo<3,2-c>quinoline 
• 139366-51-1 2-(4-Chloro-quinolin-3-yl)-2-methanesulfonyl-1-phenyl-ethanone 

Relevant articles and documents

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Electrochemical-Oxidation-Promoted Direct N-ortho-Selective Difluoromethylation of Heterocyclic N-Oxides

An efficient and green electrochemical N-ortho-selective difluoromethylation method of various quinoline and isoquinoline N-oxides has been developed. In this method, sodium difluoromethanesulfinate (HCF2SO2Na) was used as the source of the difluoromethyl moiety, and various N-ortho-selective difluoromethylation quinoline and isoquinoline N-oxides were obtained in good to excellent yields under a constant current. In addition, the reaction was easy to scale up and maintained a good yield. Preliminary mechanism studies suggested that the reaction undergoes a free-radical addition and hydrogen elimination pathway.

SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution

A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.

Deoxygenative Amination of Azine-N-oxides with Acyl Azides via [3 + 2] Cycloaddition

A transition-metal-free deoxygenative C-H amination reaction of azine-N-oxides with acyl azides is described. The initial formation of an isocyanate from the starting acyl azide via a Curtius rearrangement can trigger a [3 + 2] dipolar cycloaddition of polar N-oxide fragments to generate the aminated azine derivative. The applicability of this method is highlighted by the late-stage and sequential amination reactions of complex bioactive compounds, including quinidine and fasudil. Moreover, the direct transformation of aminated azines into various bioactive N-heterocycles illustrates the significance of this newly developed protocol.