| Identification | Back Directory | [Name]
3,5-dichloro-4-formylbenzoic acid | [CAS]
153203-80-6 | [Synonyms]
Lusutrombopag Impurity 8
3,5-dichloro-4-formylbenzoic acid
Ethane,1-bromo-2-(5-methoxyethoxy)-
Benzoic acid, 3,5-dichloro-4-formyl- | [Molecular Formula]
C8H4Cl2O3 | [MDL Number]
MFCD24483956 | [MOL File]
153203-80-6.mol | [Molecular Weight]
219.02 |
| Chemical Properties | Back Directory | [Boiling point ]
366.7±42.0 °C(Predicted) | [density ]
1.592±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
DMSO (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
3.04±0.10(Predicted) | [color ]
White to Pale Beige | [InChI]
InChI=1S/C8H4Cl2O3/c9-6-1-4(8(12)13)2-7(10)5(6)3-11/h1-3H,(H,12,13) | [InChIKey]
KNZHVHRJCNWQKI-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC(Cl)=C(C=O)C(Cl)=C1 |
| Hazard Information | Back Directory | [Synthesis]
To the reactor was added 3,5-dichlorobenzoic acid (190 g, 1.0 mmol), which was dissolved with anhydrous THF (1 L) and cooled to -78 °C. Under the condition of maintaining the reaction temperature, n-butyllithium (2.5 M, 0.5 L) was slowly added dropwise. Subsequently, N,N-dimethylformamide (95 g, 1.3 mmol) was added slowly and the titration process lasted for 2 hours. The reaction mixture was slowly warmed up to room temperature until the feedstock completely disappeared. After completion of the reaction, the reaction was quenched with a half-saturated ammonium chloride solution and the organic phase was extracted with ethyl acetate. The organic phase was concentrated to give a white solid. Finally, purification by pulping using mixed petroleum ether/ethyl acetate solvent gave 3,5-dichloro-4-formylbenzoic acid (179 g, 82% yield). | [References]
[1] Patent: CN106565625, 2017, A. Location in patent: Paragraph 0073-0074
[2] Patent: CN104341316, 2017, B. Location in patent: Paragraph 0379; 0381; 0382 |
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