Conditions | Yield |
---|---|
Stage #1: formaldehyd With triethylamine; magnesium chloride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Reflux; Stage #2: 4-methoxy-phenol In tetrahydrofuran Reflux; | 100% |
Stage #1: formaldehyd With triethylamine; magnesium chloride In tetrahydrofuran at 20 - 25℃; for 0.166667h; Stage #2: 4-methoxy-phenol In tetrahydrofuran Reflux; | 100% |
Stage #1: formaldehyd With triethylamine; magnesium chloride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Stage #2: 4-methoxy-phenol In tetrahydrofuran for 16h; Inert atmosphere; Reflux; | 99% |
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; for 12h; Inert atmosphere; | 98% |
With aluminum (III) chloride In dichloromethane at 20℃; for 12h; Inert atmosphere; | 98% |
With beryllium(II) chloride In toluene for 7h; | 95% |
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h; | 47% |
Stage #1: 2,5-dimethoxybenzaldehyde With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 4h; Stage #2: With water In dichloromethane at 0℃; |
2-hydroxy-5-methoxybenzyl alcohol
2-hydroxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
With air; (acryl-TEMPO)-co-(allylamine-treated chlorophyll b-Co(III) complex) immobilized on SiO2-covered Fe3O4 magnetic nanoparticles In water at 25℃; for 0.416667h; | 96% |
With oxygen In ethanol at 20℃; under 760.051 Torr; for 0.5h; Catalytic behavior; Green chemistry; | 95% |
With dihydrogen peroxide at 20℃; for 3.6h; Catalytic behavior; Green chemistry; | 94% |
Conditions | Yield |
---|---|
With sodium hydroxide In water for 1h; Heating; | 72% |
With sodium hydroxide Reimer-Tiemann reaction; Heating; | 65% |
With sodium hydroxide at 70 - 80℃; for 0.5h; | 48% |
1-(o-hydroxy-5-methoxyphenyl)-3-phenylpropargylic alcohol
A
2-hydroxy-5-methoxybenzaldehyde
B
1,4-diphenyl-1,3-butadiyne
Conditions | Yield |
---|---|
With copper(II) acetate monohydrate In acetonitrile for 2h; Reflux; | A n/a B 72% |
5-methoxy-2-(prop-2-yn-1-yloxy)benzaldehyde
A
2-hydroxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate; tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide electrochem. reaction; magnesium rod anode, nickel foam grid cathode; | A 30% B 65% |
Conditions | Yield |
---|---|
Reimer-Tiemann reaction; | 60% |
Multi-step reaction with 2 steps 1: 40 percent / BF3*Et2O / CH2Cl2 / 14 h / Ambient temperature 2: 47 percent / H2O, HgO, BF3*Et2O / tetrahydrofuran / 1 h / Ambient temperature View Scheme |
2-[1,3]Dithiolan-2-yl-4-methoxy-phenol
2-hydroxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; water; mercury(II) oxide In tetrahydrofuran for 1h; Ambient temperature; | 47% |
hexamethylenetetramine
4-methoxy-phenol
A
2-hydroxy-5-methoxybenzaldehyde
B
2-hydroxy-5-methoxyisophthaldehyde
Conditions | Yield |
---|---|
In trifluoroacetic acid for 24h; | A n/a B 32% |
Conditions | Yield |
---|---|
in ein zuvor auf 165grad erhitztes Gemisch von Glycerin und Borsaeure bei 150grad und Behandeln des Reaktionsgemisches mit wss.H2SO4 bei 115grad; | |
With toluene-4-sulfonic acid In acetic acid for 5h; Duff Aldehyde Synthesis; Reflux; Inert atmosphere; |
2,5-Dihydroxybenzaldehyde
dimethyl sulfate
A
2-hydroxy-5-methoxybenzaldehyde
B
2,5-dimethoxybenzaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
(i) SOCl2, Py, PE, (ii) H2, quinoline, sulfur, Pd-BaSO4, xylene; Multistep reaction; |
tris(phenylthio)methane
4-methoxy-phenol
2-hydroxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
With dimethyl(methylthio)sulfonium tetrafluoroborate; water 1.) CH2Cl2, room temp., 2 h; Yield given. Multistep reaction; |
N,N-diethyl-O-(4-methoxyphenyl)carbamate
N,N-dimethyl-formamide
A
2-hydroxy-5-methoxybenzaldehyde
B
O-(2-formyl-4-methoxy)phenyl N,N-diethylcarbamate
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium 1.) THF, -78 deg C, 1 h, 2.) to room temp., 8 to 12 h; Yield given. Multistep reaction. Yields of byproduct given; |
2-t-butoxy-5-methoxybenzaldehyde
2-hydroxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
With trifluoroacetic acid |
Conditions | Yield |
---|---|
With hydroxide In 1,4-dioxane; water at 37℃; Rate constant; Thermodynamic data; var. temp., ΔH(excit.), ΔS)(excit.); |
Conditions | Yield |
---|---|
With ethylmagnesium bromide; triethylamine 1.) THF, RT, 20 min, 2.) C6H6, reflux, 2.5 h; Yield given. Multistep reaction; |
2-acetoxy-5-methoxybenzaldehyde
A
2-hydroxy-5-methoxybenzaldehyde
B
acetic acid
2-iodo-5-methoxybenzaldehyde
2-hydroxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 12 percent / t-BuOK, CuCl, pyridine / 1,2-dimethoxy-ethane / 3 h / Heating 2: CF3COOH View Scheme | |
Multi-step reaction with 2 steps 1: 1.) CuCl, 2.) pyridine, 1,3-dinitrobenzene / 1.) DME, 2.) reflux, 3 h 2: CF3COOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 59 percent / I2, H5IO6 / acetic acid; H2O; H2SO4 / 2 h / 80 °C 2: 12 percent / t-BuOK, CuCl, pyridine / 1,2-dimethoxy-ethane / 3 h / Heating 3: CF3COOH View Scheme | |
Multi-step reaction with 3 steps 1: 59 percent / I2, H5IO6 / acetic acid; H2O; H2SO4 / 2 h / 80 °C 2: 1.) CuCl, 2.) pyridine, 1,3-dinitrobenzene / 1.) DME, 2.) reflux, 3 h 3: CF3COOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium persulfate; NaOH-solution; alkali / 30 - 35 °C / und Erhitzen des Reaktionsprodukts mit konz.Salzsaeure auf 70grad 2: aqueous NaOH-solution View Scheme |
2-(2-hydroxy-5-methoxyphenyl)-4-phenoxymethyl-1,3-dioxolane
A
2-hydroxy-5-methoxybenzaldehyde
B
1-phenoxy-2,3-propanediol
Conditions | Yield |
---|---|
With water In methanol at 20℃; Quantum yield; Irradiation; | A n/a B 96 %Chromat. |
2-(2-hydroxy-5-methoxyphenyl)-5-phenyl-1,3-dioxane
A
2-hydroxy-5-methoxybenzaldehyde
B
2-phenylpropane-1, 3-diol
Conditions | Yield |
---|---|
With water In methanol at 20℃; Quantum yield; Irradiation; | A n/a B 59 %Chromat. |
2-(2-hydroxy-5-methoxyphenyl)-1,3-dioxolane
A
2-hydroxy-5-methoxybenzaldehyde
B
ethylene glycol
Conditions | Yield |
---|---|
With water In methanol at 20℃; Quantum yield; Irradiation; | A n/a B 100 %Spectr. |
2-(2-hydroxy-5-methoxyphenyl)-5,5-dimethyl-1,3-dioxane
A
2-hydroxy-5-methoxybenzaldehyde
B
2,2-Dimethyl-1,3-propanediol
Conditions | Yield |
---|---|
With water In methanol at 20℃; Quantum yield; Irradiation; | A n/a B 100 %Spectr. |
N,N-dimethyl-formamide
A
2-Hydroxy-4-methoxybenzaldehyde
B
2-hydroxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide; 4-methoxy-2-(trimethylsilyl)phenyl triflate With tetrabutyl ammonium fluoride at 20℃; for 3h; Inert atmosphere; Stage #2: With water |
Conditions | Yield |
---|---|
With chloroform; potassium hydroxide In water at 60℃; for 15h; Reimer-Tiemann Phenol Formylation; |
Conditions | Yield |
---|---|
With magnesium chloride In acetonitrile Reflux; |
Conditions | Yield |
---|---|
Stage #1: 2-hydroxy-5-methoxybenzaldehyde With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 1h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 2.25h; Cooling with ice; Stage #3: With hydrogenchloride In tetrahydrofuran; water pH=< 2; | 100% |
With potassium hydroxide; hydrazine In ethylene glycol at 150℃; for 19h; Wolf-Kishner reduction; Inert atmosphere; | 98% |
With palladium 10% on activated carbon; hydrogen In acetic acid; ethyl acetate at 20℃; for 20h; | 98% |
2-hydroxy-5-methoxybenzaldehyde
acrylonitrile
6-methoxy-2H-chromene-3-carbonitrile
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane for 20h; Heating; | 100% |
With 1,4-diaza-bicyclo[2.2.2]octane for 12h; Reflux; | 91.3% |
With 1,4-diaza-bicyclo[2.2.2]octane at 50℃; for 20h; Addition; condenzation; | 79% |
2-hydroxy-5-methoxybenzaldehyde
allyl bromide
2-allyloxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran Inert atmosphere; Reflux; | 100% |
With potassium carbonate In acetonitrile Heating; | 99% |
With potassium carbonate In acetonitrile for 1h; Heating; | 99% |
2-hydroxy-5-methoxybenzaldehyde
propargyl bromide
5-methoxy-2-(prop-2-yn-1-yloxy)benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In acetone Substitution; Heating; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 3h; Inert atmosphere; | 100% |
With potassium carbonate In acetonitrile at 20℃; for 24h; | 95% |
2-hydroxy-5-methoxybenzaldehyde
benzyl bromide
2-benzyloxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 60℃; Inert atmosphere; | 100% |
With caesium carbonate In acetone at 20℃; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; | 100% |
2-hydroxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane at 70℃; for 0.5h; | 100% |
5-methylisoxazol-3-ylamine
2-hydroxy-5-methoxybenzaldehyde
4-methoxy-2-[(5-methyl-3-isoxazolyl)imino]methylphenol
Conditions | Yield |
---|---|
Reflux; | 100% |
In ethanol for 2h; Reflux; | 90% |
2-hydroxy-5-methoxybenzaldehyde
{(1R,3R,4S,6S)-4-amino-4,7,7-trimethylbicyclo[4.1.0]heptan-3-yl}methanol
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 100% |
2-hydroxy-5-methoxybenzaldehyde
2-hydroxy-5-methoxybenzyl alcohol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 20℃; for 1h; | 99.7% |
With sodium tetrahydroborate | 85% |
With sodium tetrahydroborate In ethanol at 20℃; Cooling with ice; | 85% |
2-hydroxy-5-methoxybenzaldehyde
diethyl malonate
6-methoxycoumarin-3-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 2-hydroxy-5-methoxybenzaldehyde; diethyl malonate With piperidine; acetic acid In ethanol for 9h; Reflux; Stage #2: With ethanol; water; sodium hydroxide for 0.25h; Reflux; | 99.2% |
2-hydroxy-5-methoxybenzaldehyde
prenyl bromide
5-methoxy-2-(3-methylbut-2-enyloxy)benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide Ambient temperature; | 99% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 2h; | |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h; | |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h; | |
Stage #1: 2-hydroxy-5-methoxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: prenyl bromide In N,N-dimethyl-formamide at 20℃; |
2-hydroxy-5-methoxybenzaldehyde
N,N-phenylbistrifluoromethane-sulfonimide
trifluoro-methanesulfonic acid 2-formyl-4-methoxy-phenyl ester
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere; | 99% |
With potassium carbonate In tetrahydrofuran at 120℃; for 0.1h; microwave heating; | 87% |
With triethylamine | |
With potassium carbonate In tetrahydrofuran at 120℃; for 0.1h; Microwave irradiation; |
2-hydroxy-5-methoxybenzaldehyde
p-toluenesulfonyl chloride
toluene-4-sulfonic acid 2-formyl-4-methoxy-phenyl ester
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; water Inert atmosphere; | 99% |
With potassium carbonate In acetonitrile at 20℃; for 12h; | 91% |
With sodium hydroxide In dichloromethane; water at 20℃; | 71% |
2-hydroxy-5-methoxybenzaldehyde
tert-butyldimethylsilyl chloride
2-tert-butyldimethylsiloxy-5-methoxyphenyl carboxaldehyde
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 25℃; for 16h; Inert atmosphere; | 99% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; | 97% |
With 1H-imidazole In N,N-dimethyl-formamide at 80℃; for 20h; | 90% |
Conditions | Yield |
---|---|
With poly(N,N'-dibromo-N-ethyl-benzene-1,3-disulfonamide) In ethanol; water at 20℃; for 3h; | 99% |
With diethylamine In ethanol at 20℃; for 2.5h; Green chemistry; | 94% |
With piperidine In ethanol at 20℃; |
Conditions | Yield |
---|---|
With piperidine In ethanol for 2.5h; Knoevenagel condensation; Heating; | 99% |
2-hydroxy-5-methoxybenzaldehyde
4-bromoethylbutanoate
ethyl 4-(2-formyl-4-methoxyphenoxy)butanoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 1h; | 99% |
2-hydroxy-5-methoxybenzaldehyde
ethyl 5-bromovalerate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 99% |
2-hydroxy-5-methoxybenzaldehyde
(E)-5-methoxy-2-hydroxybenzaldehyde oxime
Conditions | Yield |
---|---|
With pyridine; hydroxylamine hydrochloride In ethanol at 60℃; for 3h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With [(1,5-cyclooctadiene)(OH)iridium(I)]2 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; Schlenk technique; Sealed tube; diastereoselective reaction; | 99% |
2-hydroxy-5-methoxybenzaldehyde
6-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-one
Conditions | Yield |
---|---|
With triethylamine In neat (no solvent) at 20℃; for 0.0833333h; Sonication; | 99% |
2-hydroxy-5-methoxybenzaldehyde
Cinnamyl bromide
2-allyloxy-5-methoxybenzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; | 99% |
2-hydroxy-5-methoxybenzaldehyde
4-hydroxy-1-methyl-2(1H)-quinolone
tributylphosphine
Conditions | Yield |
---|---|
With pyrrolidine; benzoic acid In tetrahydrofuran at 30℃; for 1h; Schlenk technique; Inert atmosphere; | 99% |
2-hydroxy-5-methoxybenzaldehyde
propylmaleimide
D-alanine methyl ester hydrochloride
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 125℃; for 0.5h; Microwave irradiation; Green chemistry; diastereoselective reaction; | 99% |
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; | 99% |
2-hydroxy-5-methoxybenzaldehyde
ethyl (triphenylphosphoranylidene)acetate
6-methoxycoumarin
Conditions | Yield |
---|---|
With N,N-diethylaniline Wittig reaction; Reflux; | 98% |
With N,N-diethylaniline at 210 - 215℃; for 2.5h; | 93.4% |
With N,N-diethylaniline for 2.5h; Heating; | 93% |
The 2-Hydroxy-5-methoxybenzaldehyde with cas registry number of 672-13-9 is clear yellow liquid which is sensitive to air. This chemical is also known as 5-Methoxysalicylaldehyde. Its systematic name is called Benzaldehyde, 2-hydroxy-5-methoxy-. And its IUPAC name is named as 2-hydroxy-5-methoxybenzaldehyde. This chemical belongs to the following categories: Aromatic Aldehydes & Derivatives (substituted); Benzaldehyde; Adehydes, Acetals & Ketones; Anisoles, Alkyloxy Compounds & Phenylacetates; Phenols. It has the EINECS registry number of 211-589-0.
The physical properties about this chemical are: (1)ACD/LogP: 1.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.52; (4)ACD/LogD (pH 7.4): 1.5 ; (5)#H bond acceptors: 3; (6)#H bond donors: 1; (7)#Freely Rotating Bonds: 3; (8)Index of Refraction: 1.587; (9)Molar Refractivity: 41.56 cm3; (10)Molar Volume: 123.5 cm3; (11)Surface Tension: 47.3 dyne/cm; (12)Density: 1.231 g/cm3; (13)Flash Point: 108.1 °C; (14)Enthalpy of Vaporization: 50.43 kJ/mol; (15)Boiling Point: 247.5 °C at 760 mmHg; (16)Vapour Pressure: 0.0162 mmHg at 25°C ; (17)Refractive index: 1.577-1.579.
Preparation of 2-Hydroxy-5-methoxybenzaldehyde: it can be made by 4-methoxy-phenol with 60% yield.
Uses of 2-Hydroxy-5-methoxybenzaldehyde: this chemical can react with nitroethene to give 6-methoxy-3-nitro-2H-chromene by using reagent n-Bu2NH and solvent CHCl3 at temperature 80 ℃. The reaction time is about 24 hours with 72% yield.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. Therefore, wear suitable protective clothing during using it to avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=Cc1cc(ccc1O)OC;
(2)InChI: InChI=1/C8H8O3/c1-11-7-2-3-8(10)6(4-7)5-9/h2-5,10H,1H3;
(3)InChIKey: FZHSPPYCNDYIKD-UHFFFAOYAD
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 125mg/kg (125mg/kg) | BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 228, 1954. |
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