3,5-DICHLOROSALICYLALDEHYDE Chemical Properties

Melting point:

95-97 °C (lit.)

Boiling point:

273.68°C (rough estimate)

Density 

1.4410 (rough estimate)

refractive index 

1.4590 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

ethanol: soluble5%, clear, faintly yellow to greenish-yellow

form 

Crystalline Powder

pka

6.27±0.23(Predicted)

color 

Pale yellow

Water Solubility 

Insoluble in water. Solubility in methanol is almost transparent.

Sensitive 

Air Sensitive

BRN 

973391

InChI

InChI=1S/C7H4Cl2O2/c8-5-1-4(3-10)7(11)6(9)2-5/h1-3,11H

InChIKey

FABVMBDCVAJXMB-UHFFFAOYSA-N

SMILES

C(=O)C1=CC(Cl)=CC(Cl)=C1O

CAS DataBase Reference

90-60-8(CAS DataBase Reference)

EPA Substance Registry System

Benzaldehyde, 3,5-dichloro-2-hydroxy- (90-60-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29121900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,5-DICHLOROSALICYLALDEHYDE Usage And Synthesis

Chemical Properties

pale yellow crystalline powder

Uses

3,5-Dichlorosalicylaldehyde has been used in the preparation of Schiff base ligands and (RS)-3,5-dichloro-2-[[(1-phenylethyl)imino]methyl]phenol.

Uses

3,5-Dichlorosalicylaldehyde has been used in the preparation of:

• Schiff base ligands
• (RS)-3,5-dichloro-2-[[(1-phenylethyl)imino]methyl]phenol

Synthesis

The general procedure for the synthesis of 3,5-dichlorosalicylaldehyde from urotropine and 2,4-dichlorophenol was as follows: first, 2,4-dichlorophenol (10.0 g, 61.3 mmol) and hexamethylenetetetramine (17.2 g, 122.6 mmol) were dissolved in 80 mL of methanesulfonic acid, and the reaction mixture was heated and stirred for 1.5 hours at 100 °C. After the reaction was completed, the reaction mixture was diluted with ethyl acetate, and the organic layer was washed sequentially with water and saturated sodium bicarbonate solution, and then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure to give the crude product. The crude product was purified by column chromatography using ethyl acetate/hexane gradient elution to afford the target compound 3,5-dichloro-2-hydroxybenzaldehyde (INT-01) as a yellow oil (7.5 g, 64% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ11.39 (s, 1H), 7.64 (s, 1H), 7.52 (s, 1H). Liquid chromatography (LC) analytical conditions: C-18 column, 5 min to 95% acetonitrile/water gradient elution, flow rate 1.7 mL/min, detection wavelength 254 nm, column temperature 23 ℃, retention time (tr) = 3.95 min.

References

[1] Patent: WO2015/109011, 2015, A1. Location in patent: Paragraph 0205; 0206
[2] Patent: WO2015/109014, 2015, A1. Location in patent: Paragraph 0204; 0205
[3] Patent: US2015/197500, 2015, A1. Location in patent: Paragraph 0263; 0264
[4] Chemical & Pharmaceutical Bulletin, 1983, vol. 31, # 5, p. 1751 - 1753
[5] Journal of the Chemical Society, 1941, p. 547,549

3,5-DICHLOROSALICYLALDEHYDE(90-60-8)Related Product Information

• 3,5,6-Trichlorosalicylic acid
• 6,8-DICHLORO-3-FORMYLCHROMONE
• 3,5-DICHLOROSALICYLALDEHYDE
• 3,5-Dichlorosalicylic acid
• 3',5'-DICHLORO-2'-HYDROXYACETOPHENONE
• 3,3',4',5-TETRACHLOROSALICYLANILIDE
• S(-)-RACLOPRIDE L-TARTRATE
• 3,5-DICHLORO-2,6-DIMETHOXYBENZOIC ACID
• CYS-ASP-PRO-GLY-TYR-ILE-GLY-SER-ARG
• 4,6-DICHLOROSALICYLALDEHYDE
• Salicylaldehyde
• 3,5-DICHLORO-2-METHOXYBENZOIC ACID
• 1-(3,5-DICHLORO-2-HYDROXYPHENYL)PROPAN-1-ONE
• OXALIC ACID BIS[2,4,5-TRICHLORO-6-(PENTYLOXYCARBONYL)PHENYL] ESTER
• ETHYL 2-(2,4-DICHLORO-6-FORMYLPHENOXY)ACETATE
• 6,8-Dichloro Chromone
• 6,8-DICHLORO-3-CYANOCHROMONE
• 6,8-DICHLORO-3-METHYLCHROMONE