Conditions | Yield |
---|---|
Stage #1: difluoromethyl phenyl sulfide; 1,2,4-trimethoxy-benzene With tin(IV) chloride In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dichloromethane; water; dimethyl sulfoxide at 20℃; for 2h; | 98% |
(2,4,5-trimethoxyphenyl)methanol
asaraldehyde
Conditions | Yield |
---|---|
With copper(l) iodide; TEMPOL; N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine In acetonitrile at 20℃; for 2h; Inert atmosphere; | 97% |
With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In dichloromethane at 0℃; for 1.5h; Molecular sieve; Inert atmosphere; | 96% |
With tert.-butylhydroperoxide; eosin y In decane; acetonitrile at 25℃; for 36h; Inert atmosphere; Irradiation; Molecular sieve; Green chemistry; chemoselective reaction; | 87% |
Conditions | Yield |
---|---|
With sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran; water microwave irradiation; | 84% |
With sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran; water Microwave irradiation; | 82% |
asarone
asaraldehyde
Conditions | Yield |
---|---|
With sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran; water at 100℃; Microwave irradiation; | 83% |
With chromium(VI) oxide | |
With potassium permanganate |
Conditions | Yield |
---|---|
With sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran; water at 100℃; Microwave irradiation; | 83% |
With sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran; water for 0.0138889h; microwave irradiation; | 82% |
With dipyridinium dichromate; acetic acid In 1,4-dioxane for 0.333333h; Heating; Microwave irradiation; | |
With potassium permanganate; sodium hydrogencarbonate at 20℃; |
Conditions | Yield |
---|---|
With trichlorophosphate at 20℃; for 1h; Vilsmeier reaction; | 81% |
With trichlorophosphate at 0 - 80℃; for 3h; Vilsmeier-Haack Formylation; Inert atmosphere; | 80% |
With trichlorophosphate |
asaraldehyde
Conditions | Yield |
---|---|
With ammonium acetate for 0.0125h; microwave irradiation; | 77% |
C16H18N2O3
A
asaraldehyde
B
4,5-bis(2,4,5-trimethoxyphenyl)-2-phenyl-2H-1,2,3-triazole
Conditions | Yield |
---|---|
With copper(II) acetate monohydrate In toluene at 60℃; for 7h; | A n/a B 66% |
N-(chloromethyl)diformamide
1,2,4-trimethoxy-benzene
A
asaraldehyde
B
tris(2,4,5-trimethoxyphenyl)methane
Conditions | Yield |
---|---|
With aluminum (III) chloride In chlorobenzene at 0 - 18℃; for 22h; | A 56% B 24% |
5-ethenyl-1,2,4-trimethoxybenzene
asaraldehyde
Conditions | Yield |
---|---|
With 1-hydroxy-pyrrolidine-2,5-dione; graphitic carbon nitride; oxygen In acetonitrile at 20℃; Inert atmosphere; Irradiation; | 52% |
1,2,4-trimethoxy-benzene
trimethyl orthoformate
A
asaraldehyde
B
tris(2,4,5-trimethoxyphenyl)methane
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In neat liquid at 20℃; for 1h; Friedel-Crafts Alkylation; | A 30% B 46% |
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at 20℃; for 2h; Inert atmosphere; | A 37% B 6% C 42% |
With aluminum (III) chloride In dichloromethane at 20℃; for 2h; Inert atmosphere; | A 7% B 23% C 6% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; palladium diacetate; 3-trifluoromethylaniline In dichloromethane at 60℃; for 24h; Sealed tube; | 33% |
difluoromethyl phenyl sulfide
1,2,4-trimethoxy-benzene
A
asaraldehyde
B
tris(2,4,5-trimethoxyphenyl)methane
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 20℃; for 2h; Inert atmosphere; | A 20% B 3% C 24% D 25% |
Conditions | Yield |
---|---|
With hydrogenchloride; aluminium trichloride; benzene at 40 - 50℃; Zersetzung des Reaktionsgemisches mit Eiswasser; |
Conditions | Yield |
---|---|
With potassium permanganate; water |
Conditions | Yield |
---|---|
With sodium hydroxide; dipotassium peroxodisulfate | |
Multi-step reaction with 3 steps 1: Br2; NaClO3 2: CuCl 3: NaOH View Scheme |
Conditions | Yield |
---|---|
With potassium carbonate; acetone |
Conditions | Yield |
---|---|
With potassium carbonate; acetone |
Conditions | Yield |
---|---|
With potassium carbonate; acetone |
methanol
α-asarone
A
C12H16O3
B
asaraldehyde
C
3-Methoxy-3-(2,4,5-trimethoxyphenyl)-propan
Conditions | Yield |
---|---|
for 4h; Irradiation; |
C12H16O3
A
α-asarone
B
asaraldehyde
C
andamanicin
D
(Z)-3-(2,4,5-trimethoxyphenyl)acrylaldehyde
Conditions | Yield |
---|---|
for 720h; Irradiation; Further byproducts given; | A 0.26 g B 1.18 g C 0.28 g D 46 mg |
C12H16O3
A
α-asarone
B
asaraldehyde
C
andamanicin
D
(Z)-3-(2,4,5-trimethoxyphenyl)acrylaldehyde
E
trans 2,4,5-trimethoxy cinnamaldehyde
Conditions | Yield |
---|---|
for 720h; Mechanism; Irradiation; | A 0.26 g B 1.18 g C 0.28 g D 46 mg E 0.19 g |
C12H16O3
A
α-asarone
B
asaraldehyde
C
andamanicin
D
trans 2,4,5-trimethoxy cinnamaldehyde
Conditions | Yield |
---|---|
for 720h; Irradiation; Further byproducts given; | A 0.26 g B 1.18 g C 0.28 g D 0.19 g |
Conditions | Yield |
---|---|
With sodium dichromate In acetic acid; benzene for 6h; Heating; |
asaraldehyde
Conditions | Yield |
---|---|
With sodium hydrogensulfite beim Stehen an der Luft; | |
With water; sodium hydrogensulfite |
2-acetyl-6-allylphenol
asaraldehyde
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 191h; | 100% |
With potassium hydroxide In ethanol for 191h; aldol condensation; |
asaraldehyde
1,2,4-trimethoxy-5-methylbenzene
Conditions | Yield |
---|---|
With triethylsilane; chloro-trimethyl-silane In acetonitrile | 100% |
Multi-step reaction with 2 steps 1: hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 0.12 h / Irradiation 2: KOH / bis-(2-hydroxy-ethyl) ether / 0.28 h / Irradiation View Scheme |
Conditions | Yield |
---|---|
at 20℃; for 12h; | 100% |
diethoxyphosphoryl-acetic acid ethyl ester
asaraldehyde
2,4,5-trimethoxycinnamic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran for 20h; Horner-Wadsworth-Emmons reaction; Reflux; | 100% |
Nitroethane
asaraldehyde
2,4,5-trimethoxy-β-methyl-β-nitrostyrene
Conditions | Yield |
---|---|
With ammonium acetate for 0.75h; Reflux; | 99.5% |
With ammonium acetate | |
With ammonium acetate In acetic acid |
asaraldehyde
2-hydroxy-4,5-dimethoxybenzaldehyde
Conditions | Yield |
---|---|
Stage #1: asaraldehyde With boron trichloride In dichloromethane at -78 - 20℃; for 3h; Stage #2: With hydrogenchloride; water In dichloromethane at 0℃; | 99% |
With boron tribromide In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; | 99% |
With boron trichloride In dichloromethane at -78 - 20℃; for 3h; | 98% |
Conditions | Yield |
---|---|
Stage #1: asaraldehyde; 2-iodophenylamine With acetic acid In methanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol at 0 - 20℃; for 95h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With indium(III) bromide In water at 20℃; for 3h; | 98% |
N,N'-diacetylpiperazin-2,5-dione
asaraldehyde
1-Acetyl-3-[1-(2,4,5-trimethoxy-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione
Conditions | Yield |
---|---|
With potassium tert-butylate; tert-butyl alcohol In dichloromethane at 20℃; for 4h; | 98% |
asaraldehyde
4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
1-methyl-3-propyl-5-(2,4,5-trimethoxyphenyl)-1H-pyrazolo[4,3-d]pyrimidin-7-(6H)-one
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate In water; dimethyl sulfoxide at 100℃; for 0.05h; Sealed tube; Microwave irradiation; | 98% |
Stage #1: asaraldehyde; 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide In ethanol at 60℃; for 0.5h; Stage #2: With oxygen; copper dichloride In ethanol at 75℃; for 0.5h; | 87% |
asaraldehyde
(2,4,5-trimethoxyphenyl)methanol
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique; | 97% |
With sodium tetrahydroborate In methanol for 0.5h; | 84% |
With ethanol; platinum Hydrogenation; |
Conditions | Yield |
---|---|
97% | |
With toluene-4-sulfonic acid In toluene for 3h; Heating / reflux; | 96% |
With toluene-4-sulfonic acid In toluene for 3h; Heating / reflux; | 96% |
asaraldehyde
1-hydroxy-1-(2,4,5-trimethoxyphenyl)propan-2-one
Conditions | Yield |
---|---|
Stage #1: (1-methoxyethyl)triphenylphosphonium tetrafluoroborate With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #2: asaraldehyde In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With hydrazine hydrate In water at 60℃; for 0.666667h; Green chemistry; | 97% |
Conditions | Yield |
---|---|
With indium(III) bromide In dichloromethane at 20℃; for 1h; | 96% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol for 2h; Heating; | 96% |
asaraldehyde
4-bromo-4'-acetylbiphenyl
1-[(4-(4-bromophenyl)phenyl)]-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
Conditions | Yield |
---|---|
In methanol at 75℃; Claisen-Schmidt condensation; Ionic liquid; Microwave irradiation; | 96% |
asaraldehyde
1-(2,4,6-trimethoxyphenyl)ethanone
(2E)-1-(2,4,6-trimethoxyphenyl)-3-(2,4,5-trimethoxyphenyl)-2-propen-1-one
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation; | 96% |
With lithium hydroxide monohydrate In ethanol at 20℃; for 168h; Claisen-Schmidt Condensation; | 78% |
With lithium hydroxide monohydrate In ethanol at 20℃; for 168h; Claisen-Schmidt Condensation; | 78% |
With potassium hydroxide at 20℃; for 0.0833333h; Claisen-Schmidt Condensation; Inert atmosphere; | 68% |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 20℃; for 0.5h; | 95% |
With potassium hydroxide In methanol at 20℃; for 1h; |
3-(3',4',5'-trimethoxyphenyl)-4,5,6-trimethoxy-indan-1-one
asaraldehyde
3-(3',4',5'-trimethoxyphenyl)-4,5,6-trimethoxy-2-(2'',4'',5''-trimethoxybenzylidene)-indan-1-one
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 20℃; | 95% |
asaraldehyde
acetophenone
(2E)‑1‑phenyl‑3‑(2,4,5‑trimethoxyphenyl)prop‑2‑en‑1‑one
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation; | 95% |
With sodium hydroxide In ethanol at 20℃; for 3h; Claisen-Schmidt Condensation; | 82% |
With potassium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation; | 79% |
With sodium hydroxide In ethanol at 20℃; for 48h; Claisen-Schmidt Condensation; | 74% |
With sodium hydroxide at 20℃; for 48h; Claisen-Schmidt Condensation; | 31% |
asaraldehyde
2,5-diacetoxyacetophenone
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation; | 95% |
Conditions | Yield |
---|---|
With hydrazine hydrate In water at 60℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Green chemistry; | 95% |
cycl-isopropylidene malonate
asaraldehyde
5-(2,4,5-trimethoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 12h; Ambient temperature; | 94% |
In methanol at 20℃; for 6h; | 46% |
In methanol at 20℃; Knoevenagel condensation; | |
In N,N-dimethyl-formamide |
asaraldehyde
methyl 2-naphthyl ketone
(2E)-1-(2-naphthyl)-3-(2,4,5-trimethoxyphenyl)-2-propen-1-one
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 20℃; for 24h; | 94% |
With potassium hydroxide In methanol at 20℃; for 24h; |
asaraldehyde
para-bromoacetophenone
1-(4-bromophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
Conditions | Yield |
---|---|
In methanol at 75℃; Claisen-Schmidt condensation; Ionic liquid; Microwave irradiation; | 94% |
With sodium hydroxide In ethanol for 2h; |
asaraldehyde
1-(4-methoxyphenyl)ethanone
(E)-1-(4-methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
Conditions | Yield |
---|---|
Stage #1: 1-(4-methoxyphenyl)ethanone With sodium hydroxide In ethanol; water at 20℃; for 0.0833333h; Claisen-Schmidt Condensation; Stage #2: asaraldehyde at 20℃; Claisen-Schmidt Condensation; | 94% |
With lithium hydroxide monohydrate In ethanol at 20℃; for 15h; Claisen-Schmidt Condensation; | 92% |
With lithium hydroxide monohydrate In ethanol at 20℃; for 15h; Claisen-Schmidt Condensation; | 92% |
N-hydroxyphthalimide
asaraldehyde
1,3-dioxoisoindolin-2-yl 2,4,5-trimethoxybenzoate
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In decane; ethyl acetate at 20 - 70℃; for 8h; | 94% |
1. Introduction of 2,4,5-Trimethoxy Benzaldehyde
2,4,5-Trimethoxy Benzaldehyde is pharmaceutical intermediates used for the preparation of asarone.
2. Properties of 2,4,5-Trimethoxy Benzaldehyde
Melting point: 112-114 °C
Index of Refraction: 1.524
Molar Refractivity: 53.04 cm3
Molar Volume: 173.1 cm3
Surface Tension: 35.4 dyne/cm
Density: 1.133 g/cm3
Flash Point: 149 °C
Enthalpy of Vaporization: 57.77 kJ/mol
Boiling Point: 334.7 °C at 760 mmHg
Vapour Pressure: 0.000125 mmHg at 25°C
Classification Code: Mutation data
3. Toxicity of 2,4,5-Trimethoxy Benzaldehyde
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 422mg/kg (422mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. |
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