3,4-Dimethoxyphenylacetone Chemical Properties

Melting point:

136-139 °C

Boiling point:

154-158 °C (12 mmHg)

Density 

1.115 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5358(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

clear liquid

color 

Light yellow to Yellow to Orange

Water Solubility 

Insoluble in water.

BRN 

1107410

InChI

InChI=1S/C11H14O3/c1-8(12)6-9-4-5-10(13-2)11(7-9)14-3/h4-5,7H,6H2,1-3H3

InChIKey

UMYZWICEDUEWIM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

776-99-8(CAS DataBase Reference)

NIST Chemistry Reference

3,4-Dimethoxyphenylacetone(776-99-8)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

24/25

WGK Germany 

3

RTECS 

UC1795500

HS Code 

29145090

MSDS

• Language:English Provider:3,4-Dimethoxyphenylacetone
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3,4-Dimethoxyphenylacetone Usage And Synthesis

Chemical Properties

CLEAR YELLOW TO BROWN LIQUID

Uses

3,4-Dimethoxyphenylacetone was used as starting material in the synthesis of α-methyl-dopa, an important nonproteogenic α-amino acid for pharmaceutical applications. 3,4-Dimethoxyphenylacetone undergoes asymmetric amination catalyzed by Brevibacterium linens IFO 12141 strain to yield corresponding optically active amine

Synthesis Reference(s)

Chemistry Letters, 5, p. 1239, 1976
The Journal of Organic Chemistry, 29, p. 1424, 1964 DOI: 10.1021/jo01029a039

Synthesis

GENERAL METHOD: To a THF/water (4:1, 15 mL) solution of methyl eugenol (1 mmol) was added 10% Pd/C (0.05 mmol) and KBrO3 (3 mmol). The reaction mixture was heated to reflux temperature. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was diluted with water and filtered through Whatman 40 filter paper. The filtrate was extracted with ethyl acetate and the organic layers were combined. The organic layers were washed sequentially with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography to give 3,4-dimethoxypropiophenone.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 19, p. 2293 - 2295
[2] Tetrahedron Letters, 2009, vol. 50, # 24, p. 2893 - 2894
[3] Synthesis, 1992, # 12, p. 1229 - 1231
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1975, p. 1548 - 1551

3,4-Dimethoxyphenylacetone(776-99-8)Related Product Information

• 3,4-Dimethoxyphenol
• Diphenyldimethoxysilane
• 1,1-Dimethoxyethane
• (3,4-Dimethoxyphenyl)acetic acid
• 3'-methoxypropiophenone
• 2,6-Dimethoxybenzaldehyde
• 3,4-Dimethoxybenzoic acid
• Dimethyldimethoxysilane
• 1,3-Dimethoxybenzene
• 2-(3,4-Dimethoxyphenyl)ethanol
• (3,4-Dimethoxyphenyl)acetonitrile
• 3,4-Dimethoxyacetophenone
• Veratraldehyde
• Dimethoxymethane
• Propiophenone
• 1-Deuteriopropan-2-one
• 2,5-DIMETHOXYPROPIOPHENONE
• Rotenone