776-99-8

Basic information

• Product Name: 3,4-Dimethoxyphenylacetone
• Synonyms: Veratone;Veratrum ketone;3,4-DIMETHOXYPHENYLACETONE / METHYL VERATRYL KETONE;3,4-DIMETHOXYPHENYLACETONE 97+%;VERATRYL ACETONE;1-(3,4-dimethoxyphenyl)acetone;1-(3,4-DIMETHOXYPHENYL)-2-PROPANONE;1-ACETONYL-3,4-DIMETHOXYBENZENE
• CAS NO: 776-99-8
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• EINECS: 212-285-0
• Product Categories: Building Blocks;C11 to C12;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Aromatic Ketones (substituted);C11 to C12;Carbonyl Compounds;Ketones
• Mol File: 776-99-8.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 154-158 °C (12 mmHg)
• Flash Point: >230 °F
• Appearance: colorless transparent liquid
• Density: 1.115 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00349mmHg at 25°C
• Refractive Index: n20/D 1.5358(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• BRN: 1107410
• CAS DataBase Reference: 3,4-Dimethoxyphenylacetone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dimethoxyphenylacetone(776-99-8)
• EPA Substance Registry System: 3,4-Dimethoxyphenylacetone(776-99-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: UC1795500
• Hazardous Substances Data: 776-99-8(Hazardous Substances Data)

Usage

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

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

Synthetic route

methylmagnesium bromide (75-16-1) + 3,4-dimethoxyphenylacetic acid N,O-dimethylhydroxyamide (155955-78-5) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
In tetrahydrofuran at 0℃;	93%

bis(acetonitrile)palladium(II) dichloride + 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) → 3,4-dimethoxyphenylacetone (776-99-8) + 1-(3,4-dimethoxyphenyl)-2,2-dimethoxypropane

Conditions	Yield
	A 91% B n/a

4-Bromoveratrole (2859-78-1) + acetone (67-64-1) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; caesium carbonate at 90℃; for 16h; Inert atmosphere; sealed vial;	88%

methanol (67-56-1) + 3,4-dimethoxy-β-methyl-β-nitrostyrene (122-47-4, 37629-53-1) → 3,4-dimethoxyphenylacetone (776-99-8) + 1-(3,4-dimethoxy-phenyl)-1-methoxy-propan-2-one oxime

Conditions	Yield
With indium; chloro-trimethyl-silane at 25℃; for 3.5h; Reduction; Addition;	A n/a B 87%

C18H20O3N2 + benzaldehyde (100-52-7) → 3,4-dimethoxyphenylacetone (776-99-8) + (Z)-N'-benzylidenebenzohydrazide (14850-88-5)

Conditions	Yield
With chloro-trimethyl-silane; sodium iodide In acetonitrile	A n/a B 30%

C13H18O4N2 + 4-bromo-benzaldehyde (1122-91-4) → C9H9N2O2Br + 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
With chloro-trimethyl-silane; sodium iodide In acetonitrile	A 25% B n/a

diazomethane (186581-53-3, 908094-01-9) + 1-(3,4-dihydroxyphenyl)-2-propanone (2503-44-8) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
With diethyl ether

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
With lead acetate

4-isopropenyl-1,2-dimethoxybenzene (30405-75-5) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
With hypoiodous acid Einw. von AgNO3 oder HgO auf das gebildete Jodhydrin;

dimethylcadmium (506-82-1) + 3,4-dimethoxyphenylacetyl chloride (10313-60-7) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
With diethyl ether

1,2-dimethoxy-4-(E)-propenylbenzene (6379-72-2) + lead(IV) tetraacetate (546-67-8) + acetic acid (64-19-7) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
at 60℃; Kochen des Reaktionsprodukts mit wss. H2SO4;

α-(3,4-dimethoxyphenyl)acetoacetonitrile (18133-46-5, 63895-79-4) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
With sulfuric acid

Methylisoeugenol (93-16-3) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
With lead(II,IV) oxide; acetic acid
With lead(IV) acetate; acetic acid at 50 - 60℃; Durch Erhitzen des Reaktionsprodukts mit wss. H2SO4;

((Z)-2-Bromo-1-methyl-vinyloxy)-trimethyl-silane (61668-34-6) + 3,4-dimethoxyphenylmagnesium bromide (89980-69-8) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
(i) Ni catalyst, (ii) aq. HCl; Multistep reaction;

1,2-epoxy-3-(3,4-dimethoxyphenyl)propane (27602-80-8) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
lithium iodide In various solvent(s) at 130℃; for 5h; Yield given;

(-)-Saucerneol (88497-86-3) → 3,4-dimethoxyphenylacetone (776-99-8) + (S)-8-(4-Hydroxy-3-methoxy-phenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ol (36531-08-5, 78341-26-1, 88034-60-0, 88547-66-4, 95782-56-2)

Conditions	Yield
hydrogen cation constitution;

manassantin B (88497-88-5) → 3,4-dimethoxyphenylacetone (776-99-8) + 1-(1,3-benzodioxol-5-yl)-2-propanone (4676-39-5) + (S)-8-(4-Hydroxy-3-methoxy-phenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ol (36531-08-5, 78341-26-1, 88034-60-0, 88547-66-4, 95782-56-2)

Conditions	Yield
hydrogen cation constitution;

manassantin A (88497-87-4) → 3,4-dimethoxyphenylacetone (776-99-8) + (S)-8-(4-Hydroxy-3-methoxy-phenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ol (36531-08-5, 78341-26-1, 88034-60-0, 88547-66-4, 95782-56-2)

Conditions	Yield
toluene-4-sulfonic acid In benzene constitution;

N-Butyl-N'-tert-butyl-N-[(E)-2-(3,4-dimethoxy-phenyl)-1-methyl-vinyl]-formamidine (95018-66-9) → 3,4-dimethoxyphenylacetone (776-99-8)

Conditions	Yield
With boron trifluoride diethyl etherate; acetic acid; hydrazine 1.) EtOH, H2O, 2.) acetone, RT, 24 h; Yield given. Multistep reaction;

3,4-dimethoxyphenylacetone (776-99-8) → 1-(3,4-dimethoxyphenyl)-2-propanol (19578-92-8)

Conditions	Yield
With zirconium dioxide hydrate; isopropyl alcohol at 130℃; for 0.666667h; Meerwein-Ponndorf-Verley Reduction;	100%
With sodium tetrahydroborate In methanol at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;	96%
With sodium tetrahydroborate In ethanol at 20℃; for 0.5h;	95%

3,4-dimethoxyphenylacetone (776-99-8) → 2-(3,4-dimethoxyphenyl)-1-methylethylamine (120-26-3)

Conditions	Yield
Stage #1: 3,4-dimethoxyphenylacetone With ammonium acetate; sodium acetate; sodium cyanoborohydride; acetic acid In methanol at 20℃; for 18h; pH=6 - 7; Stage #2: With sodium hydroxide In methanol; water pH=14;	99%
With sodium cyanoborohydride In methanol; water	67%
With sodium cyanoborohydride In methanol; water	67%

3,4-dimethoxyphenylacetone (776-99-8) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → 3-Hydroxy-2-methyl-3-veratryl-buttersaeureaethylester (4676-40-8)

Conditions	Yield
With zinc In benzene for 4h; Reformatsky Reaction; Inert atmosphere; Reflux;	98.2%

3,4-dimethoxyphenylacetone (776-99-8) + malononitrile (109-77-3) → 2-(1-(3,4-dimethoxyphenyl)propan-2-ylidene)malononitrile

Conditions	Yield
With ammonium acetate; acetic acid In benzene at 120℃; Knoevenagel Condensation; Dean-Stark;	97%
Knoevenagel Condensation;

3,4-dimethoxyphenylacetone (776-99-8) + methyl iodide (74-88-4) → 3-(3',4'-dimethoxyphenyl)butan-2-one (4156-24-5)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique;	96%
With sodium hydride In tetrahydrofuran 1.) 0 deg C to room temperature, 30 min, 2.) 0 deg C, 1 h; room temperature, 4 h;	92%
(i) NaOiPr, iPrOH, (ii) /BRN= 969135/; Multistep reaction;

3,4-dimethoxyphenylacetone (776-99-8) → veratronitrile (2024-83-1)

Conditions	Yield
With iron; sodium nitrite In dimethyl sulfoxide at 90℃; for 20h; Reagent/catalyst; Solvent; Sealed tube; Inert atmosphere;	95%

3,4-dimethoxyphenylacetone (776-99-8) → (S)-1-(3,4-dimethoxyphenyl)propan-2-ol (161121-02-4)

Conditions	Yield
With Rhodococcus ruber alcohol dehydrogenase; NAD; isopropyl alcohol; magnesium chloride In aq. phosphate buffer at 30℃; for 48h; pH=7; Catalytic behavior; Reagent/catalyst; Time; Inert atmosphere; Schlenk technique; Enzymatic reaction; enantioselective reaction;	94%
With lyophilized-rehydrated Debaryomyces hansenii cells; isopropyl alcohol In water at 28℃; for 1h;	64%
With D-glucose In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Reagent/catalyst; Temperature; pH-value; Enzymatic reaction; stereoselective reaction;	63.9%

3,4-dimethoxyphenylacetone (776-99-8) + methyl iodide (74-88-4) → 3-(3,4-dimethoxyphenyl)-3-methylbutan-2-one (4461-99-8)

Conditions	Yield
Stage #1: 3,4-dimethoxyphenylacetone With sodium hydride In tetrahydrofuran; mineral oil at -5 - 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 3h; Inert atmosphere;	93%

3,4-dimethoxyphenylacetone (776-99-8) + methylamine (74-89-5) → 1-(3,4-dimethoxyphenyl)-N-methylpropan-2-amine (33236-61-2)

Conditions	Yield
Stage #1: 3,4-dimethoxyphenylacetone; methylamine With sodium tetrahydroborate In methanol; water at 4℃; for 0.5h; Stage #2: With hydrogenchloride In methanol; water pH=1; Stage #3: With sodium hydroxide In methanol; water pH=13;	92%
Stage #1: 3,4-dimethoxyphenylacetone; methylamine In methanol; water at 0℃; for 0.5h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol; water at 0 - 20℃; for 1.5h; Inert atmosphere;	69%
With hydrogen; palladium on activated charcoal In ethanol
With hydrogenchloride; sodium cyanoborohydride In methanol

3,4-dimethoxyphenylacetone (776-99-8) + 2-Amino-1-phenylethanol (7568-93-6) → N-[2-(3,4-dimethoxyphenyl)-1-methylethyl]-2-hydroxy-2-phenylethylamine (62717-86-6)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol at 25℃; for 15h;	92%

3,4-dimethoxyphenylacetone (776-99-8) + 4-Chlorobutanoyl chloride (4635-59-0) → 1-(3-chloropropyl)-6,7-dimethoxy-3-methylbenzo[c]pyrylium hexachlorostannate

Conditions	Yield
With tin(IV) chloride In dichloromethane for 3h; Heating;	92%

3,4-dimethoxyphenylacetone (776-99-8) + ethylamine (75-04-7) → [2-(3,4-dimethoxy-phenyl)-1-methyl-ethyl]-ethyl amine (33236-62-3)

Conditions	Yield
Stage #1: 3,4-dimethoxyphenylacetone; ethylamine With sodium cyanoborohydride; acetic acid In methanol at 0 - 20℃; for 96h; pH=6.5 - 7; Stage #2: With hydrogenchloride In methanol; water pH=1;	92%

3,4-dimethoxyphenylacetone (776-99-8) + ethyl iodide (75-03-6) → 3-(3,4-dimethoxyphenyl)pentan-2-one

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide; sodium hydroxide In methanol at 10 - 60℃; for 6.25h;	91%

3,4-dimethoxyphenylacetone (776-99-8) + methyl 2-cyano-3,3-bis(methylsulfanyl)acrylate (3490-92-4) → 5-(3,4-dimethoxyphenyl)-6-methyl-4-(methylsulfanyl)-2-oxo-2H-pyran-3-carbonitrile (136358-76-4)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide	89%
With potassium hydroxide In N,N-dimethyl-formamide

3,4-dimethoxyphenylacetone (776-99-8) + 1,1'-((4-chlorophenyl)methylene)diurea (55718-52-0) → 4-(4-chlorophenyl)-5-(3,4-dimethoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

Conditions	Yield
With caesium carbonate In ethanol at 70℃; for 24h;	89%

2-aminopyridine (504-29-0) + 3,4-dimethoxyphenylacetone (776-99-8) → 3-(3,4-dimethoxyphenyl)-2-methylimidazo[1,2-a]pyridine

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile at 80℃; for 5h;	86%

3,4-dimethoxyphenylacetone (776-99-8) + 4-(4-methyl-1-piperidinyl)-6-(1-naphthyl)-2-oxo-2H-pyran-3-carbonitrile (454703-36-7) → 3',4'-dimethoxy-2-methyl-4-(4"-methylpiperidin-1"-yl)-6-(naphthalen-1'''-yl)biphenyl-3-carbonitrile

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 6h; Michael Addition;	85%

3,4-dimethoxyphenylacetone (776-99-8) + ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate (17823-58-4) → 5-(3,4-dimethoxyphenyl)-6-methyl-4-(methylsulfanyl)-2-oxo-2H-pyran-3-carbonitrile (136358-76-4)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 10h;	84%
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 10h;

3,4-dimethoxyphenylacetone (776-99-8) + thiourea (17356-08-0) → 5-(3,4-dimethoxyphenyl)-4-methylthiazol-2-amine

Conditions	Yield
With cesium bicarbonate; Bromotrichloromethane In acetonitrile at 80℃; for 2h;	83%

Upstream product

• 27602-80-8 4-(2,3-epoxypropyl)-1,2-dimethoxybenzene 
• 60-29-7 diethyl ether 
• 30405-75-5 4-isopropenyl-1,2-dimethoxybenzene 
• 7553-56-2 iodine 
• 67-56-1 methanol 
• 122-47-4 3,4-dimethoxy-β-methyl-β-nitrostyrene 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 10535-17-8 1-(3,4-dimethoxyphenyl)-2-(methoxyphenoxy)propane-1,3-diol 
• 19578-92-8 1-(3,4-dimethoxyphenyl)-2-propanol 
• 107951-82-6 1,2-Dimethoxy-4-[2-methylsulfanyl-2-(toluene-4-sulfonyl)-propyl]-benzene 
• 95018-66-9 N-Butyl-N'-tert-butyl-N-[(E)-2-(3,4-dimethoxy-phenyl)-1-methyl-vinyl]-formamidine 
• 17639-93-9 2-chloro-propionic acid methyl ester 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 88497-86-3 (-)-Saucerneol 

Downstream Products

• 4676-42-0 α,β-dimethyl-γ-(3,4-dimethoxyphenyl) butyrolactone 
• 892-02-4 5-(3,4-dimethoxy-benzyl)-5-methyl-imidazolidine-2,4-dione 
• 2543-46-6 (±)-3-(3,4-dimethoxyphenyl)-2-amino-2-methylpropanenitrile 
• 19578-92-8 1-(3,4-dimethoxyphenyl)-2-propanol 
• 38007-20-4 1-acetoxy-1-(3,4-dimethoxy-phenyl)-acetone 
• 25083-95-8 1-bromo-1-(3',4'-methoxyphenyl)propan-2-one 
• 115247-49-9 (4,5-dimethoxy-2-nitro-phenyl)-acetone 
• 102550-50-5 N,N'-bis-[2-(3,4-dimethoxy-phenyl)-1-methyl-ethyl]-hydrazine 
• 856374-60-2 2-[2-(3,4-dimethoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 146655-87-0 1-(3,4-dimethoxoxyphenyl)-4-phenyl-3-buten-2-one 
• 128340-60-3 (Z)-3-(3,4-Dimethoxy-phenyl)-4-morpholin-4-yl-but-3-en-2-one 
• 68081-10-7 1,5-Bis(3,4-dimethoxyphenyl)-2-methyl-2-pentanol 
• 58379-92-3 N-(1-methyl-2-(3,4-dimethoxy-phenyl)-ethyl)-N-methyl-hydroxylamine 
• 53751-40-9 veratryl acetate 

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