| Identification | More | [Name]
1-Chloroisoquinoline | [CAS]
19493-44-8 | [Synonyms]
1-CHLOROISOQUINOLINE
1-CHLOROISOQUINOLINE, 98.0+%(GC)
chloroisoquinoline
1-Chloroisoquinoline, 97+% | [EINECS(EC#)]
628-561-2 | [Molecular Formula]
C9H6ClN | [MDL Number]
MFCD00024134 | [Molecular Weight]
163.6 | [MOL File]
19493-44-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to yellow low melting solid, crystals and/or | [Melting point ]
31-36 °C (lit.) | [Boiling point ]
274-275 °C/768 mmHg (lit.) | [density ]
1.2108 (rough estimate) | [refractive index ]
1.6342 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [form ]
Low Melting Solid, Crystals and/or Chunks | [pka]
2.03±0.30(Predicted) | [color ]
White to yellow | [Water Solubility ]
Insoluble in water. | [BRN ]
2996 | [InChIKey]
MSQCQINLJMEVNJ-UHFFFAOYSA-N | [CAS DataBase Reference]
19493-44-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29334900 |
| Hazard Information | Back Directory | [Chemical Properties]
white to yellow low melting solid, crystals and/or | [Uses]
1-Chloroisoquinone is used in the preparation of new aminoisoquinolinylurea derivatives which show antiproliferative activity against melanoma cell lines. It can also be applied to the control of stor
age and stability of unstable boronic acids. | [Uses]
Used in a Mn-catalyzed cross-coupling with aryl- and alkylmagnesium halides.1 Also used in a Pd-catalyzed cross-coupling with heteroaryl boronic acids and esters.2 | [Synthesis]
The general procedure for the synthesis of 1-chloroisoquinoline from isoquinoline-N-oxide was as follows: phosphoryl chloride (200 mL) was slowly added dropwise to isoquinoline-N-oxide (20.0 g) under ice bath cooling conditions. Subsequently, the reaction mixture was heated to 105 °C and refluxed overnight. Upon completion of the reaction, the excess phosphoryl chloride was removed by distillation under reduced pressure. The residue was quenched with ice water and extracted with dichloromethane. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography using a mixed solvent of ethyl acetate and petroleum ether as eluent to afford the target product 1-chloroisoquinoline (21.0 g, 85% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.25-8.31 (m, 2H), 8.08 (d, J = 8.0 Hz, 1H), 7.88-7.91 (m, 2H), 7.80-7.84 (m, 1H). Mass spectrometry (ESI+) showed a molecular ion peak m/z 164.0. HPLC analysis (Method A) showed a retention time (Rt) of 8.29 min and a purity of 96.0%. | [References]
[1] Organic Letters, 2015, vol. 17, # 12, p. 2948 - 2951
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
[3] Patent: WO2013/92979, 2013, A1. Location in patent: Page/Page column 54
[4] Journal of Organic Chemistry, 1998, vol. 63, # 20, p. 6886 - 6890
[5] Tetrahedron: Asymmetry, 1993, vol. 4, # 4, p. 743 - 756 |
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