Tetrahydro-2H-pyran-4-carbonyl chloride Chemical Properties

Boiling point:

50 °C

Density 

1.201±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Almost colorless

InChIKey

RYGUCYSSMOFTSH-UHFFFAOYSA-N

CAS DataBase Reference

40191-32-0

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

14-20/21/22-29-34-36-52/53

Safety Statements 

23-24/25-36/37/39-45-26-61

RIDADR 

3265

HazardClass 

IRRITANT

HS Code 

29339900

Tetrahydro-2H-pyran-4-carbonyl chloride Usage And Synthesis

Chemical Properties

Colorless to light yellow liquid

Synthesis

In a 50 mL three-necked round-bottomed flask, 6.85 g (52.6 mmol) of tetrahydropyran-4-carboxylic acid, 9.79 g (82.3 mmol) of thionyl chloride, and 10 mL of toluene were sequentially added, and a stirrer, thermometer, and reflux condenser were assembled. The reaction system was placed in an oil bath at 80 °C and the reaction was continuously stirred for 1.5 hours. At the end of the reaction, the solvent and excess thionyl chloride were removed by distillation under reduced pressure to afford 7.81 g (100% yield) of tetrahydropyran-4-carbonyl chloride as a light brown liquid. The product was characterized as follows: 1H-NMR (CDCl3, δ/ppm): 1.79-1.93 (2H, m), 1.99-2.06 (2H, m), 2.91-3.00 (1H, m), 3.40-3.49 (2H, m), 3.97-4.03 (2H, m); CI-MS (m/z): 131 [M+1]+.

References

[1] Patent: US2008/306287, 2008, A1. Location in patent: Page/Page column 6
[2] Patent: WO2008/71948, 2008, A2. Location in patent: Page/Page column 11-12
[3] Helvetica Chimica Acta, 1997, vol. 80, # 5, p. 1528 - 1551
[4] Journal of the Chemical Society, 1930, p. 2525,2529
[5] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 6, p. 2426 - 2436

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