3,5-Dichlorosalicylaldehyde
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3,5-Dichlorosalicylaldehyde
structure -
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CAS No:
90-60-8
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Formula:
C7H4Cl2O2
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Chemical Name:
3,5-Dichlorosalicylaldehyde
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Synonyms:
Benzaldehyde,3,5-dichloro-2-hydroxy-;Salicylaldehyde,3,5-dichloro-;3,5-Dichloro-2-hydroxybenzaldehyde;3,5-Dichlorosalicylaldehyde;2-Hydroxy-3,5-dichlorobenzaldehyde;NSC 96393;2,4-Dichloro-6-formylphenol
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CAS No:
3,5-Dichlorosalicylaldehyde Basic Attributes
191.007
191.01
202-005-5
96393
DTXSID2059011
2913000090
Characteristics
37.3
2.8
pale yellow crystalline powder
1.5±0.1 g/cm3
95 °C
236.7ºC at 760 mmHg
96.9±25.9 °C
1.644
Insoluble in water. Solubility in methanol is almost transparent.
Safety Information
NONH for all modes of transport
3
R36/37/38
S26-S36
Xi: Irritant;
P261-P305 + P351 + P338
H315-H319-H335
|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 43 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3,5-Dichlorosalicylaldehyde Use and Manufacturing
Chromene acids are made starting from phenols via salicylic aldehydes. 2, 4- Dichlorophenol (10.0 g, 61.3 mmol) and hexamethylenetetramine (17.2 g, 122.6 mmol) were dissolved in 80 mL methanesulfonic acid and heated at 100 C for 1.5 h. The reaction was diluted with ethyl acetate and the organic layer was washed with water, followed by saturated sodium bicarbonate, dried over magnesium sulfate, and evaporated. The product 3, 5-dichloro-2- hydroxybenzaldehyde (INT-01) was purified by chromatography using ethyl acetate/hexane gradient to give a yellow oil (7.5 g, 64percent yield). 1H NMR (400 MHz, CDC10205] Chromene acids are made starting from phenols via salicylic aldehydes. 2, 4- Dichlorophenol (10.0 g, 61.3 mmol) and hexamethylenetetramine (17.2 g, 122.6 mmol) were dissolved in 80 mL methanesulfonic acid and heated at 100 C for 1.5 h. The reaction was diluted with ethyl acetate and the organic layer was washed with water, followed by saturated sodium bicarbonate, dried over magnesium sulfate, and evaporated. The product 3, 5-dichloro-2- hydroxybenzaldehyde (INT-01) was purified by chromatography using ethyl acetate/hexane gradient to give a yellow oil (7.5 g, 64percent yield). 1H NMR (400 MHz, CDC1Step 1: 3, 5-Dichloro-2-hydroxybenzaldehyde (INT-01)Chromene acids are made starting from phenols via salicylic aldehydes. 2, 4-Dichlorophenol (10.0 g, 61.3 mmol) and hexamethylenetetramine (17.2 g, 122.6 mmol) were dissolved in 80 mE methanesulfonic acid and heated at 1000 C. for 1.5 h. The reaction was diluted with ethyl acetate and the organic layer was washed with water, followed by saturated sodium bicarbonate, dried over magnesium sulfate, and evaporated. The product 3, 5-dichioro-2-hydroxy- benzaldehyde (INT-Ol) was purified by chromatography using ethyl acetate/hexane gradient to give a yellow oil (7.564percent yield). ‘H NMR (400 MHz, CDC13) ö 11.39 (s, 1H), 7.64 (s, 1H), 7.52 (s, 1H). EC tr=3.95 mm (C-18 column, 5 to 95percent acetonitrile/water over 6 mm at 1.7 mE/mm with detection 254 nm, at 23° C.).To a three-neckflask, equipped with a reflux condenser, thermometer, anitrogen source, and magnetic stirrer, was added 2, 4-dichlorophenol (12 mmol), urotropine (24 mmol), andTFA (12.4 mL). The mixture was heated to 115 °C andto refluxed for 20 h. The reaction mixture was cooled to60 °C and added 33percent sulfuric acid (6.2 mL), then thereaction mixture was heated to 130 °C and refluxed for1 h. After cooling, the reaction mixture was acidified topH 6–7 with sodium bicarbonate, and extracted withethyl acetate. The reaction was monitored by TLC. Theethyl acetate extract was treated with vacuum distillation, to give crude 3, 5-dichlorosalicylaldehyde. Thecrude product was purified by column chromatographygave pale yellow product (1.218 g, 51.9percent).
Benzaldehyde, 3,5-dichloro-2-hydroxy-: ACTIVE
Computed Properties
Molecular Weight:191.01
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:189.9588348
Monoisotopic Mass:189.9588348
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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