Benzomorpholine Chemical Properties

Boiling point:

85°C/0.75mm

Density 

1.095±0.06 g/cm3(Predicted)

refractive index 

1.60

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

clear liquid

pka

4.37±0.20(Predicted)

color 

Colorless to Yellow to Orange

Water Solubility 

Sparingly soluble in water.(0.26 g/L) (25°C),

InChI

InChI=1S/C8H9NO/c1-2-4-8-7(3-1)9-5-6-10-8/h1-4,9H,5-6H2

InChIKey

YRLORWPBJZEGBX-UHFFFAOYSA-N

SMILES

O1C2=CC=CC=C2NCC1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2934999090

Benzomorpholine Usage And Synthesis

Uses

It is used as pharmaceutical intermediate. Benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor.

Definition

ChEBI: 3,4-Dihydro-2H-1,4-benzoxazine is a benzoxazine.

Synthesis

To a suspension of 2-aminophenol (1.0 g, 9.2 mmol) and potassium carbonate (6.36 g, 46 mmol) in anhydrous DMF (10 mL) was added 1,2-dibromoethane (2.59 g, 13.8 mmol). The reaction mixture was heated at 125 °C with stirring for 15 hours. After completion of the reaction, it was cooled to room temperature, the mixture was poured into crushed ice and extracted with ethyl acetate (3 × 20 mL). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:10, v/v) as eluent to afford 3,4-dihydro-2H-benzo[b][1,4]oxazine as a red oil (0.81 g, 65% yield). The product was analyzed by LC-MS (ES-API): retention time 7.51 min; calculated value C8H9NO [M+H]+ 136.1, measured value 136.1.

References

[1] Tetrahedron Letters, 2006, vol. 47, # 44, p. 7823 - 7826
[2] Patent: WO2011/47432, 2011, A1. Location in patent: Page/Page column 88
[3] Heterocyclic Communications, 2012, vol. 18, # 3, p. 143 - 146
[4] Patent: WO2010/51374, 2010, A1. Location in patent: Page/Page column 132
[5] Patent: EP2172453, 2010, A1. Location in patent: Page/Page column 13

Benzomorpholine(5735-53-5)Related Product Information

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