2-Chloroveratraldehyde Chemical Properties

Melting point:

71-74 °C (lit.)

Boiling point:

300.9±37.0 °C(Predicted)

Density 

1.245±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

form 

Solid

color 

White to Pale Yellow

Sensitive 

Air Sensitive

BRN 

2109344

InChI

InChI=1S/C9H9ClO3/c1-12-7-4-3-6(5-11)8(10)9(7)13-2/h3-5H,1-2H3

InChIKey

SAWHDJTZESXNMM-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(OC)C(OC)=C1Cl

CAS DataBase Reference

5417-17-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29124900

MSDS

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

2-Chloroveratraldehyde Usage And Synthesis

Chemical Properties

beige-yellow to beige crystalline powder

Uses

2-Chloro-3,4-dimethoxybenzaldehyde is a useful reagent in the synthesis of the human TLR4 agonist euodenine A. 2-Chloro-3,4-dimethoxybenzaldehyde is also used as a reagent in the synthesis of novel 2-methoxyacylhydrazones as potent, selective PDE10A inhibitors with activity in animal models of schizophrenia.

Synthesis

Step 2 - Formation of 2-chloro-3,4-dimethoxybenzaldehyde: To a 100 mL solution of 8.03 g (43 mmol) of 2-chloro-3-hydroxy-4-methoxybenzaldehyde in acetonitrile was added 7.7 g (55 mmol) of powdered potassium carbonate, followed by the addition of 8.3 mL (0.13 mol) of iodomethane. The reaction mixture was slowly heated to reflux and stirred continuously at this temperature for 24 hours. Upon completion of the reaction, it was cooled to room temperature, the suspension was filtered and the filtrate was evaporated under vacuum to remove the solvent to give 8.5 g (42 mmol, 98% yield) of white solid. The resulting solid was confirmed to be 2-chloro-3,4-dimethoxybenzaldehyde by 1H NMR analysis.

References

[1] Synlett, 2014, vol. 25, # 20, p. 2891 - 2894
[2] Patent: US5866513, 1999, A

2-Chloroveratraldehyde(5417-17-4)Related Product Information

• 2,5-Dimethoxybenzaldehyde
• 2,3-Dimethoxybenzaldehyde
• 3,5-Dimethoxybenzaldehyde
• Veratraldehyde
• 2,4-Dimethoxybenzaldehyde
• Diphenyldimethoxysilane
• p-Anisaldehyde
• 3-Methoxybenzaldehyde
• 4-Dimethylaminobenzaldehyde
• 2,6-Dimethoxybenzaldehyde
• Dimethyldimethoxysilane
• 1,1-Dimethoxyethane
• o-Anisaldehyde
• Difluorochloromethane
• Quincarbate
• 5-CHLORO-2 3-DIMETHOXYBENZALDEHYDE
• 2-CHLORO-4,6-DIMEHOXYBENZALDEHYDE
• ETHYL 2-CHLORO-3,4-DIMETHOXYBENZOATE