Conditions | Yield |
---|---|
With aluminium trichloride; 1-decyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate In acetonitrile for 1.4h; Heating; | 99% |
With benzyltriphenylphosphonium dichromate In acetonitrile for 0.333333h; Oxidation; Heating; | 98% |
With benzyltriphenylphosphonium chlorochromate In dichloromethane for 0.0333333h; Oxidation; microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 42h; | 99% |
Stage #1: 3-methoxy-2-hydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; | |
Stage #1: 3-methoxy-2-hydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; | |
Stage #1: 3-methoxy-2-hydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; |
3-methoxy-2-hydroxybenzaldehyde
dimethyl sulfate
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In benzene | 98.7% |
With potassium carbonate In methanol for 2.5h; Heating; | 93% |
With potassium carbonate In benzene for 26h; Heating; | 89% |
Conditions | Yield |
---|---|
With triethylamine; magnesium chloride In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 6h; | 94.4% |
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In dichloromethane; water at 20℃; for 0.166667h; | 90% |
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydroxybenzaldehyde With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: dimethyl sulfate In acetone at 20℃; for 5h; | 89% |
With sodium hydroxide In water for 1h; Heating; | 68% |
dicobalt octacarbonyl
2,3-dimethoxyphenyl triflate
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 25℃; for 16h; Schlenk technique; Inert atmosphere; | 83% |
With triethylsilane; potassium acetate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 50℃; for 12h; Schlenk technique; Inert atmosphere; Molecular sieve; | 72% |
Conditions | Yield |
---|---|
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 4h; Sealed tube; | 82% |
1,2-Dimethoxy-3-phenethyloxymethyl-benzene
A
2-phenylethanol
B
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 12.5h; | A 75% B 73% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; | 73% |
2,3-dihydroxybenzaldehyde
methyl iodide
A
3-hydroxy-2-methoxybenzaldehyde
B
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydroxybenzaldehyde With potassium hydrogencarbonate In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 28h; Inert atmosphere; | A 72% B n/a |
Stage #1: 2,3-dihydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 18h; | A 57% B 19% |
Stage #1: 2,3-dihydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 18h; | A 57% B 19% |
With sodium hydride In dimethyl sulfoxide at 25℃; for 17h; NaH : pyrocatechlol 1.1; Yields of byproduct given; | A 52% B n/a |
4-nitrophenylboronic acid
B
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With potassium phosphate; water; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 100℃; for 18h; | A 67% B n/a |
2,3-dihydroxybenzaldehyde
methyl iodide
A
3-methoxy-2-hydroxybenzaldehyde
B
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide at 25℃; for 17h; NaH : pyrocatechlol 2.2; Yields of byproduct given; | A 58% B n/a |
2-(2,3-dimethoxyphenyl)-2-hydroxyacetonitrile
A
hydrogen cyanide
B
2,3-dimethyoxybenzaldehyde
1,2-dimethoxy-3-((1E)-prop-1-en-1-yl)benzene
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With potassium dichromate; sulfuric acid; 4-aminobenzene sulfonic acid | |
With potassium dichromate; sulfuric acid | |
With ozone; ethyl acetate at -20℃; und Erhitzen des Reaktionsgemisches mit Wasserdampf; |
3-methoxy-2-hydroxybenzaldehyde
dimethyl sulfate
A
2,3-dimethoxybenzaldehyde dimethylacetal
B
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With Pd-BaSO4; xylene at 140℃; Hydrogenation; |
Conditions | Yield |
---|---|
With oxygen; copper; sodium carbonate; copper(I) chloride 1.) CH3CN; Multistep reaction; |
2,3-dimethoxybenzoic acid
A
2,3-dimethoxybenzyl alcohol
B
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; diisobutylaluminium hydride; triethylamine 1.) CH2Cl2, 0 deg C; 2.) CH2Cl2, -78 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
hydrogenchloride
A
homopiperonylamine hydrochloride
B
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With alkaline solution |
tetrachloromethane
2,3-dimethoxybenzoyl chloride
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
at 140℃; Hydrogenation; |
Conditions | Yield |
---|---|
With benzene |
2-cyano-3t-(2,3-dimethoxy-phenyl)-acrylic acid
2,3-dimethyoxybenzaldehyde
2-benzyl-3-(2,3-dimethoxyphenyl)-5-propylcarbamoyl-2,3-dihydroisoxazole-4-carboxylic acid methyl ester
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
In tetrahydrofuran Heating; |
C-(2,3-dimethoxyphenyl)-N-benzyl-nitrone
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 73 percent / benzene / 22 h / 20 °C 2: 37 percent / methanol / 3 h / 20 °C 3: tetrahydrofuran / Heating View Scheme |
2-benzyl-3-(2,3-dimethoxyphenyl)-2,3-dihydroisoxazole-4,5-dicarboxylic acid dimethyl ester
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 37 percent / methanol / 3 h / 20 °C 2: tetrahydrofuran / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / BBr3 / CHCl3 / 1. 0 deg C, 2.5 h; 2. room temperature, overnight 2: 68 percent / NaOH / H2O / 1 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chloroform; phosphorus pentachloride 2: palladium-barium sulfate; xylene / 140 °C / Hydrogenation View Scheme |
methylamine
2,3-dimethyoxybenzaldehyde
(2,3-dimethoxy-benzylidene)-methyl-amine
Conditions | Yield |
---|---|
at 20℃; for 12h; | 100% |
In ethanol at 0 - 40℃; | 90% |
With benzene zuletzt unter Erwaermen und Entfernen des gebildeten Wassers; | |
In benzene for 2h; Reflux; | |
In ethanol; water |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; for 0.166667h; | 100% |
With sodium tetrahydroborate In ethanol for 20h; Ambient temperature; | 99% |
With sodium tetrahydroborate In methanol at 20℃; for 1h; | 99% |
1-Bromotetradecane
2,3-dimethyoxybenzaldehyde
(+/-)-1-hydroxy-1-(2.3-dimethoxy-phenyl)-pentadecane
Conditions | Yield |
---|---|
Stage #1: 1-Bromotetradecane With iodine; magnesium In diethyl ether Stage #2: 2,3-dimethyoxybenzaldehyde In diethyl ether for 4h; Reflux; | 100% |
With lithium In tetrahydrofuran at 0℃; | 63% |
tert-butylisonitrile
acetic acid
1-amino-2-propene
2,3-dimethyoxybenzaldehyde
2-(acetylallylamino)-N-tert-butyl-2-(2,3-dimethoxyphenyl)acetamide
Conditions | Yield |
---|---|
In methanol at 20℃; for 6h; Ugi reaction; | 100% |
(S)-1-Aminoindane
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
In neat (no solvent, solid phase) Milling; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent, solid phase) Milling; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent, solid phase) Milling; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent, solid phase) Milling; | 100% |
nitromethane
2,3-dimethyoxybenzaldehyde
1,2-Dimethoxy-3-((E)-2-nitro-vinyl)-benzene
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid at 22℃; for 3h; ultrasound; | 99% |
81% | |
With sodium hydroxide In methanol; water for 0.5h; Cooling with ice; | 46% |
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 16h; Wittig reaction; | 99% |
Stage #1: (2-iodo-4,5-dimethoxybenzyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran at 20℃; Wittig reaction; Further stages.; | 99% |
Conditions | Yield |
---|---|
Stage #1: 3-bromopropylamine hydrochloride With triethylamine In chloroform at 20℃; for 0.0833333h; Stage #2: 2,3-dimethyoxybenzaldehyde With magnesium sulfate In chloroform at 20℃; for 16h; | 99% |
N-(4-aminophenyl)-N'-phenylurea
2,3-dimethyoxybenzaldehyde
1-[4-(2,3-dimethoxy-benzylamino)phenyl]-3-phenylurea
Conditions | Yield |
---|---|
With sodium cyanoborohydride In methanol Reflux; Inert atmosphere; | 99% |
α,α-difluoromethyl p-tolyl sulfoxide
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -30℃; for 0.666667h; Inert atmosphere; diastereoselective reaction; | 99% |
Conditions | Yield |
---|---|
piperidine In pyridine Heating; | 98% |
With piperidine; pyridine at 120 - 130℃; Knoevenagel condensation; | 89% |
Stage #1: malonic acid; 2,3-dimethyoxybenzaldehyde With pyridine at 50℃; Inert atmosphere; Stage #2: With piperidine at 80 - 115℃; for 4h; Inert atmosphere; Stage #3: With hydrogenchloride In water | 84% |
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol at 20℃; under 760.051 Torr; for 0.75h; | 98% |
With potassium hydroxide; hydrazine In diethylene glycol at 90 - 100℃; for 1.5h; | 81% |
With hydrogenchloride; amalgamated zinc; ethanol |
benzyloxy-trimethylsilane
(2R,3R)-(E)-Methyl 2-acetoxy-3-(dimethylphenylsilyl)-hex-4-enoate
2,3-dimethyoxybenzaldehyde
(E)-(2S,5S,6R)-Methyl 2-acetoxy-6-(benzyloxy)-6-(2,3-dimethoxyphenyl)-5-methylhex-3-enoate
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 10h; | 98% |
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 18h; | 97% |
Conditions | Yield |
---|---|
With lithium chloride In N,N-dimethyl-formamide for 22h; Heating; | 98% |
With aluminum (III) chloride In dichloromethane at -5 - 25℃; | 94% |
With cerium(III) chloride; sodium iodide In acetonitrile for 7h; dealkylation; Heating; | 89% |
With magnesium iodide for 10h; neat (no solvent); | 80% |
With n-butyllithium; lithium 4-methylpiperazin-1-ide In toluene 1.) 15 deg C, 20 min, 2.) 65-70 deg C; | 55% |
Conditions | Yield |
---|---|
With acetic acid at 60℃; for 0.333333h; Green chemistry; | 98% |
With nano-AlPO4(SO3H) In acetonitrile at 50℃; for 0.25h; | 89% |
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
Stage #1: diethyl 3-(allyloxy)-5-methoxybenzylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Horner-Wadsworth-Emmons Olefination; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran at 0℃; Reflux; | 98% |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 20℃; Claisen-Schmidt Condensation; | 98% |
3-fluoro-1-diethylphosphonomethyl-benzene
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 3-fluoro-1-diethylphosphonomethyl-benzene With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.5h; Horner-Wadsworth-Emmons Olefination; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran at 0 - 20℃; for 20h; Horner-Wadsworth-Emmons Olefination; | 98% |
2-Hydroxy-1,4-naphthoquinone
methyl 2-cyanoacetate
2,3-dimethyoxybenzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate In ethanol; water at 20℃; for 0.116667h; Sonication; | 98% |
(1S,2S)-trans-2-amino-1-indanol
2,3-dimethyoxybenzaldehyde
(+)-(1S,2S)-2-(2,3-dimethoxybenzylideneamino)indan-1-ol
Conditions | Yield |
---|---|
In benzene for 10h; | 97.1% |
morpholine
Sesamol
2,3-dimethyoxybenzaldehyde
6-((2,3-dimethoxyphenyl)(morpholino)methyl)benzo[d][1,3]dioxol-5-ol
Conditions | Yield |
---|---|
In methanol Heating; | 97% |
In neat (no solvent) at 125℃; for 0.166667h; Solvent; Reagent/catalyst; Microwave irradiation; | 87% |
In ethanol Reflux; | 57% |
Methyltriphenylphosphonium bromide
2,3-dimethyoxybenzaldehyde
1-ethenyl-2,3-dimethoxybenzene
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With sodium amide In diethyl ether at 20℃; for 10h; Inert atmosphere; Stage #2: 2,3-dimethyoxybenzaldehyde In diethyl ether at -10 - 20℃; Wittig reaction; Inert atmosphere; | 97% |
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at -30℃; for 1h; Wittig Olefination; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran at -5 - 20℃; Wittig Olefination; | 91% |
With Amberlite IR-400 In N,N-dimethyl-formamide at 95℃; for 10h; Inert atmosphere; | 86% |
Stage #1: Methyltriphenylphosphonium bromide With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 3h; Wittig Olefination; Inert atmosphere; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran for 18h; Wittig Olefination; Inert atmosphere; Reflux; | 72% |
Stage #1: Methyltriphenylphosphonium bromide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Alkaline conditions; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran at 0℃; for 12h; Inert atmosphere; |
2-amino-1-tert-butyl-4-cyanopyrrole
dimedone
2,3-dimethyoxybenzaldehyde
C26H31N3O3
Conditions | Yield |
---|---|
With L-proline In ethanol for 6h; Reflux; | 97% |
3-aminoethyl-2-[(p-trifluoromethoxy)anilino]quinazolin-4(3H)-one
2,3-dimethyoxybenzaldehyde
C26H23F3N4O4
Conditions | Yield |
---|---|
In ethanol at 75℃; for 3h; | 97% |
Structure of 2,3-Dimethoxybenzaldehyde (CAS NO.86-51-1):
IUPAC Name: 2,3-Dimethoxybenzaldehyde
Molecular Formula: C9H10O3
Molar mass: 166.1739 g/mol
Density: 1.114 g/cm3
Melting Point: 48-52 °C(lit.)
Flash Point: 105.8 °C
Boiling Point: 266.7 °C at 760 mmHg
Sensitive: air sensitive
Index of Refraction: 1.534
Molar Refractivity: 46.36 cm3
Molar Volume: 149.1 cm3
Surface Tension: 36.1 dyne/cm
Vapour Pressure: 0.00849 mmHg at 25 °C
XLogP3: 1.1
H-Bond Acceptor: 3
Rotatable Bond Count: 3
Exact Mass: 166.062994
MonoIsotopic Mass: 166.062994
Topological Polar Surface Area: 35.5
Heavy Atom Count: 12
Canonical SMILES: COC1=CC=CC(=C1OC)C=O
InChI: InChI=1S/C9H10O3/c1-11-8-5-3-4-7(6-10)9(8)12-2/h3-6H,1-2H3
InChIKey: JIVGSHFYXPRRSZ-UHFFFAOYSA-N
EINECS: 201-677-7
Product Categories: Aromatic Aldehydes & Derivatives (substituted); BenzaldehydeDerivative; Benzaldehyde; Aldehydes; C9; Carbonyl Compounds
2,3-Dimethoxybenzaldehyde (CAS NO.86-51-1) can be used as the materials for the organic synthesis intermediates. It also can be used in pharmaceutical industry for the synthesis of berberine and others.
2,3-Dimethoxybenzaldehyde has been derived from the reaction 2- methoxy-3-hydroxybenzaldehyde (o-vanillin) with dimethyl sulfate .
1. | orl-rat TDLo:7.3 mg/kg | BIPBU* Biological & pharmaceutical bulletin. 24 (2001),1277. |
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: CU5732000
Hazard Note: Irritant
HS Code: 29124900
A poison by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
2,3-Dimethoxybenzaldehyde (CAS NO.86-51-1) is also named as AI3-00141 ; NSC 403661 ; Benzaldehyde, 2,3-dimethoxy- (9CI) ; o-Veratraldehyde (8CI) . 2,3-Dimethoxybenzaldehyde (CAS NO.86-51-1) is white to brown crystalline powder.
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