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| | 4-Chloro-2-hydroxybenzaldehyde Basic information |
| | 4-Chloro-2-hydroxybenzaldehyde Chemical Properties |
| Melting point | 45.0 to 49.0 °C | | Boiling point | 229.1±20.0 °C(Predicted) | | density | 1.404±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | Chloroform (Sparingly), Methanol (Slightly) | | form | Solid | | pka | 7.21±0.10(Predicted) | | color | Off-White to Pale Brown | | InChI | InChI=1S/C7H5ClO2/c8-6-2-1-5(4-9)7(10)3-6/h1-4,10H | | InChIKey | QNZWAJZEJAOVPN-UHFFFAOYSA-N | | SMILES | C(=O)C1=CC=C(Cl)C=C1O | | CAS DataBase Reference | 2420-26-0 |
| Hazard Codes | Xn | | Risk Statements | 22 | | HS Code | 2913000090 |
| | 4-Chloro-2-hydroxybenzaldehyde Usage And Synthesis |
| Uses | 4-Chloro-2-hydroxybenzaldehyde is an intermediate used to prepare benzodiazepine diones as Hdm2 antagonists. It is also used to synthesize hydroxy-dimethyl-oxo-cyclohexenyl-dimethyl-tetrahydro-xanthenone as oral neuropeptide Y5 receptor antagonist. | | Synthesis | To a 1L three-necked round-bottomed flask was added 3-chlorophenol (33.6 g, 0.3 mol), anhydrous MgCl2 (85.7 g, 0.9 mmol), triethylamine (75.9 g, 0.75 mol) and anhydrous acetone (340 mL). The resulting solution was stirred at 25 °C for 30 min, followed by the addition of paraformaldehyde (45 g, 1.5 mol). The reaction mixture was heated to reflux for 5 h under nitrogen protection. When TLC monitoring showed complete consumption of the feedstock, the acetone was evaporated under reduced pressure. The residue was acidified to pH 3 with 10% hydrochloric acid solution and extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a brownish-red oil (18.1 g, 43.1% yield), which can be used directly in subsequent reactions without further purification (Byun et al., 2008; Uini and Lars, 1999). | | References | [1] Applied Organometallic Chemistry, 2018, vol. 32, # 2,
[2] Drug Metabolism and Disposition, 2017, vol. 45, # 12, p. 1354 - 1363
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 6, p. 1530 - 1536
[4] Organic Letters, 2015, vol. 17, # 23, p. 5824 - 5827
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 30, p. 7268 - 7274 |
| | 4-Chloro-2-hydroxybenzaldehyde Preparation Products And Raw materials |
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