2,5-Dimethoxybenzaldehyde Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2,5-Dimethoxybenzaldehyde Chemical Properties,Usage,Production

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.