4-Chloro-2-hydroxybenzaldehyde
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4-Chloro-2-hydroxybenzaldehyde
structure -
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CAS No:
2420-26-0
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Formula:
C7H5ClO2
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Chemical Name:
4-Chloro-2-hydroxybenzaldehyde
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Synonyms:
4-chlorosalicylaldehyde;4-chloro-2-hydoxybenzaldehye;4-chloro-2-hydoxybenzaldehyde;2-hydroxy-4-chlorobenzaldehyde;4-CHLORO-2-HYDROXY-BENZALDEHYDE;4-Chloro-2-hydroxy-benzaldehyde,97%;4-Chloro-2-hydroxybenzaldehyde,95+%;4-Chlorosalicylaldehyde,5-Chloro-2-formylphenol
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CAS No:
Characteristics
37.3
2.4
1.4±0.1 g/cm3
45.0 to 49.0 °C
229.1°C at 760 mmHg
92.4±21.8 °C
1.632
0.0468mmHg at 25°C
Safety Information
Xn
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-Chloro-2-hydroxybenzaldehyde Use and Manufacturing
General procedure: Into a 1 L 3-necked round-bottomflask was added 3-fluorophenol (33.6 g, 0.3 mol), anhydrous MgCl2 (85.7 g, 0.9mmol), triethylamine (75.9 g, 0.75 mol) and anhydrous acetone (340 mL). Theresulting solution was stirred at 25 °C for 30 min, followed by the addition ofparaformaldehyde (45 g, 1.5 mol). Then the reaction mixture was heated to refluxfor 5 h under a nitrogen atmosphere. Once TLC showed the consumption of startingmaterial, acetone was evaporated under vacuum. The residue was acidified to pH 3with 10percent hydrochloride and extracted with ethyl acetate (3 × 150 mL). Thecombined organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated in vacuum to afford an oily brownish red oil (18.1 g, 43.1percent in yield)which was used directly in the next reaction (Byun et al. 2008; Uini and Lars 1999).2, 3-Dichloro-5, 6-dicyano-1-4-benzoquinone (DDQ, 9.92 g, 43.7 mmol) was added to a solution of 5-chloro-2-hydroxymethylphenol in dichloromethane (65 mL) and tetrahydrofuran (15 mL), . The reaction mixture was stirred at room temperature for 4 h. Then, the solvent was evaporated under vacuum and the crude was purified by chromatography on silica to afford the title compound (72percent): 2, 3-Dichloro-5, 6-dicyano-1-4-benzoquinone (DDQ, 9.92 g, 43.7 mmol) was added to a solution of 5-chloro-2-hydroxymethylphenol in dichloromethane (65 mL) and tetrahydrofuran (15 mL).
Computed Properties
Molecular Weight:156.56
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:155.9978071
Monoisotopic Mass:155.9978071
Topological Polar Surface Area:37.3
Heavy Atom Count:10
Complexity:127
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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