| Identification | More | [Name]
9-Chloroacridine | [CAS]
1207-69-8 | [Synonyms]
9-CHLOROACRIDINE
AURORA KA-4303
9-Chloroacridine, GC 95%
9-CHLOROACRIDINE 95% | [EINECS(EC#)]
214-895-2 | [Molecular Formula]
C13H8ClN | [MDL Number]
MFCD00022266 | [Molecular Weight]
213.66 | [MOL File]
1207-69-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Green to brown solid | [Melting point ]
116-120 °C (lit.) | [Boiling point ]
346.74°C (rough estimate) | [density ]
1.1961 (rough estimate) | [refractive index ]
1.5868 (estimate) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
solid | [pka]
3.96±0.10(Predicted) | [InChI]
InChI=1S/C13H8ClN/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H | [InChIKey]
BPXINCHFOLVVSG-UHFFFAOYSA-N | [SMILES]
C1C2C(=NC3C(C=2Cl)=CC=CC=3)C=CC=1 | [CAS DataBase Reference]
1207-69-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Acridine, 9-chloro-(1207-69-8) | [EPA Substance Registry System]
1207-69-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
UN2811 | [WGK Germany ]
3
| [HS Code ]
29379000 |
| Hazard Information | Back Directory | [Chemical Properties]
Green to brown solid | [Uses]
9-Chloroacridine was employed as chromogenic reagent in the spectrophotometric method for the quantitative determination of dapsone. It was also used in the synthesis of:
- series of novel chalcones bearing acridine moiety attached to the amino group in their ring A
- new acridine derivatives
- 9-phenoxyacridine and 4-phenoxyfuro[2,3-b]quinoline derivatives
| [Synthesis]
The general procedure for the synthesis of 9-chloroacridine from acridinone was as follows: 9-acridinone (4.01 g, 21 mmol) was dissolved in phosphoryl chloride (105 mL, 1.13 mol), a magnetic stirrer was added, and the reaction was carried out at reflux for 12 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature, slowly poured into crushed ice (650 g) and the pH was adjusted to a weak base with concentrated ammonium hydroxide. The resulting light brown solid was collected by filtration, washed well with water and subsequently dried in air for 24 hours. Purification by fast column chromatography (silica gel as stationary phase, eluent was a solvent mixture of 75% hexane, 20% THF and 5% triethylamine) gave 3.97 g (89% yield) of the target product, 9-chloroacridine, as fine yellow needle-like crystals. The obtained product was confirmed to be consistent with the sample prepared by Method A by TLC, melting point determination and spectral data analysis. | [References]
[1] Pharmaceutical Sciences, 1997, vol. 3, # 5-6, p. 235 - 239
[2] European Journal of Inorganic Chemistry, 1999, # 3, p. 557 - 563
[3] Heterocycles, 2014, vol. 88, # 1, p. 535 - 546
[4] Patent: CN108640873, 2018, A. Location in patent: Paragraph 0022; 0023
[5] Chemical Biology and Drug Design, 2017, vol. 90, # 5, p. 926 - 935 |
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