9-Chloroacridine

Product Name9-Chloroacridine
CAS1207-69-8
MFC13H8ClN
MW213.66
EINECS214-895-2
MOL File1207-69-8.mol

Chemical Properties

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
pka	3.96±0.10(Predicted)
form	solid
Appearance	Light yellow to yellow Solid
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	Acridine, 9-chloro- (1207-69-8)

Safety Information

Hazard Codes	Xi,Xn
Risk Statements	36/37/38-22
Safety Statements	26-36-37/39
RIDADR	UN2811
WGK Germany	3
TSCA	TSCA listed
HS Code	29379000
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
9-Chloroacridine	English
SigmaAldrich	English
ACROS	English

Usage And Synthesis

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

578-95-0

1207-69-8

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

9-Chloroacridine

Chemical Properties

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