9-Chloroacridine 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

form 

solid

pka

3.96±0.10(Predicted)

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

HS Code 

29379000

MSDS

• Language:English Provider:9-Chloroacridine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

9-Chloroacridine 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

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(1207-69-8)Related Product Information

• Basic Orange 14
• 6,9-DIAMINO-2-ETHOXYACRIDINE LACTATE
• Amsacrine hydrochloride
• 2-ETHOXY-6,9-DIAMINOACRIDINE
• Quinacridone
• 2,9-DICHLOROACRIDINE
• 6,9-Dichloro-2-methoxyacridine
• 2-Methoxy-6-chloroacridine-9-amine
• 10-Butyl-2-chloroacridine-9(10H)-one
• Acridine
• 2,7-BIS(ALLOXYCARBONYLAMINO)-9-CHLOROACRIDINE
• 9-CHLORO-2-METHOXYACRIDINE
• 1,2,3,4-tetrahydro-9-chloroacridin
• 9-Chloroacridine
• 2-ETHOXY-6-NITRO-9-CHLORO-ACRIDINE
• 3,9-DICHLORO-7-METHOXY-2-NITROACRIDINE
• 9-amino-6-chloroacridine-2-phosphate
• 1-NITRO-4-CHLOROACRIDINE