Ethyl 1,4-Benzodioxan-2-carboxylate Chemical Properties

Boiling point:

88-95 °C/0.3 mmHg (lit.)

Density 

1.208 g/mL at 25 °C

refractive index 

n20/D 1.523

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

color 

Colorless to Yellow to Orange

InChI

InChI=1S/C11H12O4/c1-2-13-11(12)10-7-14-8-5-3-4-6-9(8)15-10/h3-6,10H,2,7H2,1H3

InChIKey

DDIGEMWIKJMEIU-UHFFFAOYSA-N

SMILES

O1C2=CC=CC=C2OCC1C(OCC)=O

CAS DataBase Reference

4739-94-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

2

HazardClass 

IRRITANT

HS Code 

2916399090

MSDS

• Language:English Provider:SigmaAldrich

Ethyl 1,4-Benzodioxan-2-carboxylate Usage And Synthesis

Uses

2,3-Dihydro-1,4-benzodioxin-2-carboxylic Acid Ethyl Ester is an intermediate used to prepare presynaptic α2-adrenoreceptor antagonists and potential antidepressants. It is also used to prepare aminoalkylbenzodioxins as calcium antagonists.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 5373, 1955 DOI: 10.1021/ja01625a050

Synthesis

GENERAL METHOD: A mixture of 12 g (0.11 mol) of catechol, 17.9 g (0.1 mol) of ethyl 2,3-dibromopropionate, and 41.4 g (0.3 mol) of anhydrous K2CO3 was refluxed for 18 hours in 200 mL of anhydrous acetone. Upon completion of the reaction, acetone was removed by distillation under reduced pressure and the residue was dissolved in dichloromethane. The organic phase was washed sequentially with water, 5% NaOH solution, 5% HCl solution and saturated NaCl solution and finally dried with anhydrous Na2SO4. After evaporating the solvent under reduced pressure, the residue was distilled to give 15.4 g (74% yield) of ethyl 1,4-benzodioxane-2-carboxylate.

References

[1] Sangita M. Kasture. “Novel enzymatic route for kinetic resolution of (±)1,4-benzodioxan-2-carboxylic acid.” Biochemical Engineering Journal 27 1 (2005): Pages 66-71.

Ethyl 1,4-Benzodioxan-2-carboxylate(4739-94-0)Related Product Information

• 1,4-Benzodioxan-2-carboxylic acid
• 1,4-Benzodioxan
• ETHYL 1,4-BENZODIOXAN-2-CARBOXYLATE
• 2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBOXYLIC ACID BUTYL ESTER
• 2-HYDROXYMETHYL-1,4-BENZODIOXANE
• ETHYL 2-METHOXYPHENOXYACETATE
• METHYL 1,4-BENZODIOXAN-2-CARBOXYLATE
• 1,4-Benzodioxane-2-carboxylic acid
• 1,4-Benzodioxan-2-carboxylic acid, 3-phenyl-, 2-(2-(diethylamino)ethox y)ethyl ester, citrate, (E)-
• CHEMBRDG-BB 5144041
• trans-2-(Diethylamino)ethyl 2,3-dihydro-3-phenyl-1,4-benzodioxin-2-car boxylate citrate