2,3-Dihydro-1,4-benzodioxine-5-carboxylic acid Chemical Properties

Melting point:

90-94 °C(lit.)

Boiling point:

334.1±41.0 °C(Predicted)

Density 

1.376±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

4.09±0.20(Predicted)

color 

Light yellow to Brown

InChI

1S/C9H8O4/c10-9(11)6-2-1-3-7-8(6)13-5-4-12-7/h1-3H,4-5H2,(H,10,11)

InChIKey

VCLSWKVAHAJSFL-UHFFFAOYSA-N

SMILES

OC(=O)c1cccc2OCCOc12

CAS DataBase Reference

4442-53-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39-36/37/38

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29329900

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich

2,3-Dihydro-1,4-benzodioxine-5-carboxylic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Synthesis

The general procedure for the synthesis of 2,3-dihydro-1,4-benzodioxane-5-carboxylic acid from 2,3-dihydrobenzo[b][1,4]dioxane-5-carboxaldehyde was as follows: 2,3-dihydrobenzo[b][1,4]dioxane-5-carboxaldehyde (0.500 g, 3.04 mmol) was dissolved in acetone (10 mL) and mixed with an aqueous solution of sulfamic acid at 0-5 °C ( 0.455 g, 4.5 mmol) was mixed and stirred. After the reaction mixture was stirred for 20 minutes, aqueous sodium chlorite (0.421 g, 4.5 mmol) was added and the reaction was continued for 18 hours at room temperature. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and quenched with water. The resulting solid was collected by filtration and dried under vacuum to afford the target product 2,3-dihydro-1,4-benzodioxane-5-carboxylic acid (0.332 g). The product was characterized as follows: 1H NMR (DMSO-d6): δ 4.27 (s, 4H), 6.84 (t, J = 7.2 Hz, 1H), 7.02 (d, J = 7.8 Hz, 1H), 7.20 (d, J = 7.5 Hz, 1H), 12.5 (bs, 1H); MS [M + H]+: 181.12.

References

[1] Patent: WO2013/153535, 2013, A1. Location in patent: Page/Page column 63

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