| Identification | More | [Name]
(R)-1,4-Benzodioxane-2-carboxylic acid | [CAS]
70918-53-5 | [Synonyms]
(R)-1,4-BENZODIOXAN 2-CARBOXYLIC ACID
(R)-1,4-BENZODIOXANE-2-CARBOXYLIC ACID
(R)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-CARBOXYLIC ACID
(R)-2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBOXYLIC ACID
(R)-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylic acid | [Molecular Formula]
C9H8O4 | [MDL Number]
MFCD00239407 | [Molecular Weight]
180.16 | [MOL File]
70918-53-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
96-99 °C | [alpha ]
83 º (c=1.5% in chloroform) | [Boiling point ]
347.2±41.0 °C(Predicted) | [density ]
1.379±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
solid | [pka]
2.69±0.20(Predicted) | [color ]
Pale yellow | [Optical Rotation]
[α]20/D +83±2°, c = 1.5% in chloroform | [BRN ]
5742837 | [InChI]
1S/C9H8O4/c10-9(11)8-5-12-6-3-1-2-4-7(6)13-8/h1-4,8H,5H2,(H,10,11)/t8-/m1/s1 | [InChIKey]
HMBHAQMOBKLWRX-MRVPVSSYSA-N | [SMILES]
OC(=O)[C@H]1COc2ccccc2O1 | [CAS DataBase Reference]
70918-53-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
2932990090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline powder | [Uses]
(R)-1,4-Benzodioxane-2-carboxylic acid is a chiral synthon mostly used in the preparation of doxazosin mesylate, a drug treating benign prostatic hyperplasia. | [Synthesis]
General procedure for the synthesis of 4-benzodioxane-2-carboxylic acid from (2,3-dihydrobenzo[b][1,4]dioxohexen-2-yl)methanol: Accurately weigh (2,3-dihydrobenzo[b][1,4]dioxohexen-2-yl)methanol, and dissolve it in 0.3 N aqueous KOH (1.3 equiv). Potassium permanganate (KMnO4, 2.0 eq.) was slowly added under ice bath conditions at 0 °C. The reaction mixture was first stirred at low temperature for about 10 minutes, then brought to room temperature and continued to stir overnight. Upon completion of the reaction, the organic phase was extracted with dichloromethane, the organic phase was washed with water sequentially, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a white solid, i.e., the crude product of 4-benzodioxane-2-carboxylic acid. The crude product was purified by silica gel fast column chromatography, and the final pure product was obtained in 92.5% yield. | [References]
[1] Patent: CN105985328, 2016, A. Location in patent: Paragraph 0063; 0071; 0072 |
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