2,5-Dimethoxybenzaldehyde Chemical Properties

Melting point:

46-48 °C (lit.)

Boiling point:

146 °C/10 mmHg (lit.)

Density 

1.1708 (rough estimate)

refractive index 

1.5260 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

795mg/l

form 

Crystalline Powder, Crystals and/or Chunks

color 

Yellow to beige

Water Solubility 

Soluble in chloroform and methanol. Slightly soluble in water.

Sensitive 

Air Sensitive

BRN 

509301

InChIKey

AFUKNJHPZAVHGQ-UHFFFAOYSA-N

LogP

1.910

CAS DataBase Reference

93-02-7(CAS DataBase Reference)

NIST Chemistry Reference

Benzaldehyde, 2,5-dimethoxy-(93-02-7)

EPA Substance Registry System

Benzaldehyde, 2,5-dimethoxy- (93-02-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-43

Safety Statements 

26-36/37/39-24/25-36

WGK Germany 

2

RTECS 

CU5740500

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29124900

MSDS

• Language:English Provider:2,5-Dimethoxybenzaldehyde
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,5-Dimethoxybenzaldehyde Usage And Synthesis

Chemical Properties

yellow crystalline solid

Uses

2,5-Dimethoxybenzaldehyde is used in the preparation of 2,5-dimethoxyphenethylamine, which is utilized to prepare psychoactive drugs such as 2,5-dimethoxy-4-bromophenethylamine, 2,5-dimethoxy-4-iodophenethylamine and 4-Chloro-2,5-dimethoxy-phenethylamine. It acts as an intermediate in organic synthesis.

Application

2,5-Dimethoxybenzaldehyde, also known as 2C-H, is an organic compound and a benzaldehyde derivative. It can be used to produce 2,5-dimethoxyphenethylamine. 2C-H is also used to produce many other substituted phenethylamines such as 2C-B, 2C-I and 2C-C.

Preparation

2,5-Dimethoxybenzaldehyde synthesis: Anethole is oxidized to anisaldehyde , which after isolation is subjected to a BaeyerVilliger oxidation reaction with performic or peracetic acid. The O-formyl-4-methoxyphenol obtained this way is hydrolyzed . 4-Methoxyphenol is subsequently formylated using the Reimer-Tiemann method and the obtained 2-hydroxy-5-methoxybenzaldehyde is methylated with dimethylsulfate to 2,5-dimethoxybenzaldehyde.
Reaction
A : Anisaldehyde from anethole via oxidative cleavage: 20 g anise oil was suspended in a mixture of 150 mL water and 30 mL conc. sulfuric acid; addition of 55 g sodium bichromate at such a rate that the temperature did not exceed 40°C. The reaction mixture was extracted with 4 x 125 mL toluene and the solvent evaporated. The residual oil was vacuum distilled to yield 9.1 g anisaldehyde.
B : O-formyl-4-methoxyphenol: 6 mL anisaldehyde was dissolved in 75 mL dichloromethane (DCM). A mixture of 12 g hydrogen peroxide and 10 mL conc. formic acid was added over 30 min. The reaction mixture was gently refluxed for 21 h.
C: B 4-methoxyphenol: Evaporating the solvent from reaction mixture and taking up the residue in 100 mL aqueous NaOH (20%) (25 mL MeOH as co-solvent) yielded 4.1 g 4-methoxyphenol as a white crystalline product after the usual work-up and purification steps.
D : Reimer-Tiemann formylation of 4-methoxyphenol: 124.1 g 4-methoxyphenol was dissolved in NaOH solution (320 g NaOH in 400 mL water). In total, 161 mL chloroform was added. The usual work-up and steam distillation yielded 109.8 g of a clear yellow oil that did not solidify upon standing at room temperature (GC/MS: 94% 2-hydroxy-5-methoxybenzaldehyde).
E: D Methylation of 2-hydroxy-5-methoxybenzaldehyde: The yellow oil from was used without further purification. A 250 mL RB flask was charged with 100 mL acetone, 14 g anhydrous potassium carbonate and 10 g 2-hydroxy-5-methoxybenzaldehyde; the mixture was brought at reflux temperature and 11 g dimethyl sulfate was added. The reaction was continued for 4 hours. The solvent is evaporated and the crude end product crystallized in cold water. Recrystallization from EtOH/water yielded 8.3 g 2,5-dimethoxybenzaldehyde (GC/MS: 98%+ 2,5-dimethoxybenzaldehyde)

Definition

ChEBI: 2,5-dimethoxy-Benzaldehyde is a dimethoxybenzene.

2,5-Dimethoxybenzaldehyde(93-02-7)Related Product Information

• 1,1-Dimethoxyethane
• Benzaldehyde
• p-Anisaldehyde
• o-Anisaldehyde
• 3-(METHOXYMETHOXY)BENZALDEHYDE
• 4-Dimethylaminobenzaldehyde
• 3-Methoxybenzaldehyde
• Diphenyldimethoxysilane
• Dimethoxymethane
• 2,4-Dimethoxybenzaldehyde
• 2',5'-Dimethoxyacetophenone
• 2,4,5-Trimethoxybenzoic acid
• Veratraldehyde
• 2,3-DIMETHOXYBENZALDEHYDE
• 2,6-Dimethoxybenzaldehyde
• 2,5-DIMETHOXYBENZOYL CHLORIDE
• KHELLIN
• 3,5-Dimethoxybenzaldehyde ,98%