| Identification | Back Directory | [Name]
4-Chloro-2-hydroxybenzaldehyde | [CAS]
2420-26-0 | [Synonyms]
4-Chlorosalicylaldehy
4-chlorosalicylaldehyde
4-Chlorosalicylaldehyde >
4-chloro-2-hydoxybenzaldehye
4-chloro-2-hydoxybenzaldehyde
2-hydroxy-4-chlorobenzaldehyde
4-CHLORO-2-HYDROXY-BENZALDEHYDE
Benzaldehyde, 4-chloro-2-hydroxy-
4-Chloro-2-hydroxy-benzaldehyde ,97%
4-Chloro-2-hydroxybenzaldehyde, 95+%
4-Bromo-2-fluoro-7-hydroxyacetophenone
4-Chlorosalicylaldehyde, 5-Chloro-2-formylphenol | [EINECS(EC#)]
695-765-6 | [Molecular Formula]
C7H5ClO2 | [MDL Number]
MFCD06252499 | [MOL File]
2420-26-0.mol | [Molecular Weight]
156.57 |
| Chemical Properties | Back Directory | [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. ]
Inert atmosphere,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 Information | Back Directory | [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 |
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