2-chloro-5,6,7,8-tetrahydroquinoline Chemical Properties

Melting point:

93-95 °C

Boiling point:

260℃

Density 

1.185

Flash point:

136℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

1.46±0.20(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C9H10ClN/c10-9-6-5-7-3-1-2-4-8(7)11-9/h5-6H,1-4H2

InChIKey

ZUXMRCHYHAWERW-UHFFFAOYSA-N

SMILES

N1C2=C(CCCC2)C=CC=1Cl

Safety Information

HS Code 

2933499090

2-chloro-5,6,7,8-tetrahydroquinoline Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-chloro-5,6,7,8-tetrahydroquinoline from 5,6,7,8-tetrahydro-2-quinolinone is as follows: 1. 20 g (0.134 mol) of 5,6,7,8-tetrahydro-2-quinolinone was added to a 250 mL two-necked flask with 28.8 mL (0.38 mol) of phosphorus trichloride (molar ratio 1:2.3) under dry conditions. 2. The reaction was rapidly stirred and heated to 135 °C and kept at reflux for 16 hours. 3. Upon completion of the reaction, the reaction mixture was cooled to 60-80 °C and then slowly poured under vigorous stirring into a 0.1% (W/V) sodium hydroxide solution pre-cooled to 0-5 °C to adjust the pH to 8.5. 4. Extract twice with 250 mL of dichloromethane at 0 °C and combine the organic phases. 5. Concentrate the organic phase by rotary evaporation to obtain the crude product. 6. The crude product was subjected to reduced pressure distillation at a pressure of 12-15 mmHg and the fractions with boiling ranges of 135-137 °C were collected to afford 20.3 g of colorless to pale yellow 2-chloro-5,6,7,8-tetrahydroquinoline liquid in 90% yield.

References

[1] Patent: CN103992270, 2016, B. Location in patent: Paragraph 0030-0033
[2] Patent: WO2006/35967, 2006, A1. Location in patent: Page/Page column 86

2-chloro-5,6,7,8-tetrahydroquinoline(21172-88-3)Related Product Information

• Tetryzoline
• Platinum dioxide
• Quinoline Yellow
• Paraformaldehyde
• IFLAB-BB F2124-0309
• 2-CHLORO-4-(TRIFLUOROMETHYL)-5,6,7,8-TETRAHYDROQUINOLINE-3-CARBONITRILE
• AKOS BB-9840
• AKOS BB-9837
• 2-CHLORO-6,6-DIMETHYL-5,6,7,8-TETRAHYDRO-3-QUINOLINECARBONITRILE
• 2-chloro-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile
• 2-CHLORO-5,6,7,8-TETRAHYDROQUINOLINE-3-CARBONITRILE
• IFLAB-BB F2124-0319
• 2-CHLORO-7,8-DIHYDRO-6H-QUINOLIN-5-ONE
• IFLAB-BB F2124-0310
• 2-chloro-5,6,7,8-tetrahydroquinoline