6-CHLOROCHROMAN-4-ONE Chemical Properties

Melting point:

97-102 °C(lit.)

Boiling point:

322.0±42.0 °C(Predicted)

Density 

1.345±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in solvents.

form 

powder to crystal

color 

White to Yellow to Orange

BRN 

124218

InChIKey

LLTDYHFVIVSQPJ-UHFFFAOYSA-N

CAS DataBase Reference

37674-72-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36-24/25

WGK Germany 

2

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

6-CHLOROCHROMAN-4-ONE Usage And Synthesis

Chemical Properties

White solid

Uses

6-Chlorochroman-4-one is used as chemical, organic intermediates for pharmaceuticals.

Synthesis

General procedure for the synthesis of 6-chlorobenzodihydropyran-4-one from 3-(p-chlorophenoxy)propionic acid: 3-(p-chlorophenoxy)propionic acid (2 g, 10 mmol) was reacted with concentrated sulfuric acid (20 mL) with stirring for 1 hour at room temperature. After completion of the reaction, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed twice with saturated aqueous sodium bicarbonate and subsequently dried with magnesium sulfate. The dried organic phase was filtered and concentrated under reduced pressure. The crude product was purified by solvent recrystallization from ethyl acetate/hexane (1:5) mixture. The resulting crystals were collected by filtration, washed with hexane and dried to give the target product 6-chlorobenzodihydropyran-4-one (1 g, 55% yield): melting point 98-101 °C (literature value: 100-101 °C); 1H NMR (DMSO-d6) δ 2.82 (t, J=6.5 Hz, 2H, 3-H2), 4.56 (t, J=6.5 Hz, 2H, 2 -H2), 7.1 (d, J=8.9 Hz, 1H, 8-H), 7.6 (dd, J=8.9 Hz/2.7 Hz, 1H, 7-H), 7.68 (d, J=2.7 Hz, 1H, 5-H); 13C NMR (DMSO-d6) δ 36.8 (C-3), 66.9 (C-2), 120.3 (C-8) 122.0 (C-4a/C-6), 125.3 (C-5), 135.6 (C-7), 160.1 (C-8a), 190.6 (C-4).

References

[1] Chinese Journal of Chemistry, 2011, vol. 29, # 4, p. 757 - 764
[2] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 834 - 844
[3] Journal of the Indian Chemical Society, 1939, vol. 16, p. 639,644
[4] Journal of the Indian Chemical Society, 1957, vol. 34, p. 467,468
[5] Journal of the American Chemical Society, 1954, vol. 76, p. 5065,5067

6-CHLOROCHROMAN-4-ONE(37674-72-9)Related Product Information

• 7-Chloro-4-chromanone
• 6-Chloro-3-chromanone
• 8-CHLOROCHROMAN-4-ONE
• 6-CHLOROCHROMAN-4-ONE
• 5'-Chloro-2'-hydroxy-3'-nitroacetophenone
• 6-CHLORO-4'-METHYLFLAVANONE
• 6-CHLORO-3',4'-DIMETHOXYFLAVANONE
• (E)-3-BENZYLIDENE-6-CHLOROCHROMAN-4-ONE
• 6-CHLORO-5-METHYLCHROMANONE
• ethyl 6-chlorochroman-4-one-2-carboxylate
• 6,8-DICHLORO-2,3-DIHYDRO-4H-CHROMEN-4-ONE
• RARECHEM BW GA 0352
• (E)-3-(4-METHYLBENZYLIDENE)-6-CHLORO-2,3-DIHYDROCHROMEN-4-ONE
• (E)-3-(4-FLUOROBENZYLIDENE)-6-CHLORO-2,3-DIHYDROCHROMEN-4-ONE
• (E)-3-(4-CHLOROBENZYLIDENE)-6-CHLORO-2,3-DIHYDROCHROMEN-4-ONE
• (E)-3-(4-BROMOBENZYLIDENE)-6-CHLORO-2,3-DIHYDROCHROMEN-4-ONE
• (E)-3-(4-METHOXYBENZYLIDENE)-6-CHLORO-2,3-DIHYDROCHROMEN-4-ONE
• BUTTPARK 83\07-45