|
|
| | 5-Fluorosalicylaldehyde Basic information |
| | 5-Fluorosalicylaldehyde Chemical Properties |
| Melting point | 82-85 °C (lit.) | | Boiling point | 56 °C / 1mmHg | | density | 1.350±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | 8.18±0.18(Predicted) | | form | Powder or Flakes | | color | White to Orange to Green | | Sensitive | Air Sensitive | | InChI | InChI=1S/C7H5FO2/c8-6-1-2-7(10)5(3-6)4-9/h1-4,10H | | InChIKey | FDUBQNUDZOGOFE-UHFFFAOYSA-N | | SMILES | C(=O)C1=CC(F)=CC=C1O | | CAS DataBase Reference | 347-54-6(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 29130000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 5-Fluorosalicylaldehyde Usage And Synthesis |
| Chemical Properties | White solid | | Uses | 5-Fluorosalicylaldehyde may be used to synthesize:
- managanese (III) complex [MnLa(μ1,3-N3)]n [H2La = N,N′-bis(5-fluorosalicylidene)-1,2-diaminoethane]
- enantiopure 4-amino-6-fluoro-3-(hydroxymethyl)chromanes
- 4,4′-difluoro-2,2′-[(hydrazine-1,2-diylidene)bis(methanylylidene)]-diphenol
- N,N′-bis(5-fluoro-2-hydroxybenzylidene)ethylenediamine
- N,N′-(2-hydroxypropane-1,3-diyl)-bis(salicylaldimine (H2L)
| | General Description | 5-Fluorosalicylaldehyde can be synthesized from 4-fluorophenol. | | Synthesis | The general procedure for the synthesis of 5-fluorosalicylaldehyde from 4-fluorophenol and trichloromethane is as follows:
Step A: To a solution of water (400mL) containing NaOH (78g, 1950mmol) was added a mixture of 4-fluorophenol (50g, 446.43mmol) in water (200mL) and ethanol (150mL). After heating the mixture to 70°C, trichloromethane (110 mL) was slowly added dropwise through the addition funnel (approximately 2 hours to complete the drop) and the reaction mixture was continuously stirred at this temperature overnight (approximately 16 hours). Upon completion of the reaction, the mixture was cooled to room temperature and acidified with 3M HCl solution. Subsequently, the reaction mixture was partitioned between saturated saline and dichloromethane, the organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography (eluent: 3% ethyl acetate/hexane) to afford 13.6 g of 5-fluorosalicylaldehyde (22% yield, white solid). | | References | [1] Journal of the American Chemical Society, 1998, vol. 120, # 33, p. 8340 - 8347
[2] Patent: WO2005/37763, 2005, A1. Location in patent: Page/Page column 126
[3] Patent: US2017/37038, 2017, A1. Location in patent: Paragraph 0372; 0373; 0374
[4] Journal of the American Chemical Society, 1946, vol. 68, p. 2502
[5] European Journal of Medicinal Chemistry, 1996, vol. 31, # 6, p. 449 - 460 |
| | 5-Fluorosalicylaldehyde Preparation Products And Raw materials |
|