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| | 2-HYDROXY-5-(TRIFLUOROMETHOXY)BENZALDEHYDE Basic information |
| | 2-HYDROXY-5-(TRIFLUOROMETHOXY)BENZALDEHYDE Chemical Properties |
| Melting point | 31-33 °C (lit.) | | Boiling point | 82 °C/60 mmHg (lit.) | | density | 1.4251 (estimate) | | Fp | >230 °F | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 7.56±0.18(Predicted) | | form | Low Melting Solid | | color | White to pale yellow | | Sensitive | Air Sensitive | | BRN | 7023825 | | InChI | 1S/C8H5F3O3/c9-8(10,11)14-6-1-2-7(13)5(3-6)4-12/h1-4,13H | | InChIKey | WQUZBERVMUEJTD-UHFFFAOYSA-N | | SMILES | Oc1ccc(OC(F)(F)F)cc1C=O | | CAS DataBase Reference | 93249-62-8(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29130000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2-HYDROXY-5-(TRIFLUOROMETHOXY)BENZALDEHYDE Usage And Synthesis |
| Chemical Properties | White to pale yellow low melting solid | | Uses | 2-Hydroxy-5-(trifluoromethoxy)benzaldehyde may be used in the preparation of :
- 2-[(E)-2-hydroxy-5-(trifluoromethoxy)benzylideneamino]-4-methylphenol
- (E)-2-((3-fluorophenylimino)methyl)-4-(trifluoromethoxy) phenol
- 2-[(E)-(naphthalen-2-ylimino) methyl]-4-(trifluoromethoxy) phenol
| | General Description | 2-Hydroxy-5-(trifluoromethoxy)benzaldehyde is formed as intermediate during the biotransformation pathways of CP-122,721 in humans. | | Synthesis | Step A: Boron tribromide (BBr3, 85.2 g, 341 mmol) was slowly added dropwise to a solution of 2-methoxy-5-(trifluoromethoxy)benzaldehyde (50.0 g, 227 mmol) in dichloromethane (DCM, 500 mL) at -20°C and under nitrogen protection. The reaction mixture was stirred at 0°C for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of ice chips, followed by pouring the mixture into an aqueous solution of saturated sodium bicarbonate (NaHCO3, 300 mL) and extracting with dichloromethane (DCM, 3 x 400 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20:1) to afford 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (38.0 g, 81.0% yield). NMR hydrogen spectrum (400 MHz, CDCl3) δ 10.97 (s, 1H), 9.87 (s, 1H), 7.43-7.38 (m, 2H), 7.02 (d, J=8.0 Hz, 1H). | | References | [1] Patent: WO2013/148851, 2013, A1. Location in patent: Paragraph 00244
[2] Patent: US2014/275172, 2014, A1. Location in patent: Paragraph 0842 |
| | 2-HYDROXY-5-(TRIFLUOROMETHOXY)BENZALDEHYDE Preparation Products And Raw materials |
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