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3,4-Dimethoxyphenylacetone

Product Name3,4-Dimethoxyphenylacetone
CAS776-99-8
MFC11H14O3
MW194.23
EINECS212-285-0
MOL File776-99-8.mol

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

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

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

93-15-2

776-99-8

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

Chemical Properties

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