Product Name

  • Name

    2-Hydroxy-5-methoxybenzaldehyde

  • EINECS 211-589-0
  • CAS No. 672-13-9
  • Article Data87
  • CAS DataBase
  • Density 1.232 g/cm3
  • Solubility Miscible with chloroform. Slightly miscible with water.
  • Melting Point 4 °C(lit.)
  • Formula C8H8O3
  • Boiling Point 247.499 °C at 760 mmHg
  • Molecular Weight 152.15
  • Flash Point 108.071 °C
  • Transport Information
  • Appearance clear yellow liquid
  • Safety 26-36-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 672-13-9 (2-Hydroxy-5-methoxybenzaldehyde)
  • Hazard Symbols IrritantXi
  • Synonyms m-Anisaldehyde,6-hydroxy- (6CI,7CI,8CI);2-Formyl-4-methoxyphenol;2-Hydroxy-5-methoxybenzaldehyde;3-Methoxy-6-hydroxybenzaldehyde;4-Hydroxy-3-formylanisole;5-Methoxy-2-hydroxybenzaldehyde;5-Methoxysalicylaldehyde;NSC 30116;
  • PSA 46.53000
  • LogP 1.21330

Synthetic route

formaldehyd
50-00-0

formaldehyd

4-methoxy-phenol
150-76-5

4-methoxy-phenol

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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%
2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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
41951-76-2

2-hydroxy-5-methoxybenzyl alcohol

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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%
chloroform
67-66-3

chloroform

4-methoxy-phenol
150-76-5

4-methoxy-phenol

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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
133503-46-5

1-(o-hydroxy-5-methoxyphenyl)-3-phenylpropargylic alcohol

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

1,4-diphenyl-1,3-butadiyne
886-66-8

1,4-diphenyl-1,3-butadiyne

Conditions
ConditionsYield
With copper(II) acetate monohydrate In acetonitrile for 2h; Reflux;A n/a
B 72%
5-methoxy-2-(prop-2-yn-1-yloxy)benzaldehyde
224317-65-1

5-methoxy-2-(prop-2-yn-1-yloxy)benzaldehyde

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

2-(1-hydroxybut-3-yn-1-yl)-4-methoxyphenol

2-(1-hydroxybut-3-yn-1-yl)-4-methoxyphenol

Conditions
ConditionsYield
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%
4-methoxy-phenol
150-76-5

4-methoxy-phenol

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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
80210-54-4

2-[1,3]Dithiolan-2-yl-4-methoxy-phenol

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; water; mercury(II) oxide In tetrahydrofuran for 1h; Ambient temperature;47%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

4-methoxy-phenol
150-76-5

4-methoxy-phenol

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

2-hydroxy-5-methoxyisophthaldehyde
73289-61-9

2-hydroxy-5-methoxyisophthaldehyde

Conditions
ConditionsYield
In trifluoroacetic acid for 24h;A n/a
B 32%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

4-methoxy-phenol
150-76-5

4-methoxy-phenol

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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
1194-98-5

2,5-Dihydroxybenzaldehyde

dimethyl sulfate
77-78-1

dimethyl sulfate

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

Conditions
ConditionsYield
With sodium hydroxide
5-methoxysalicylic acid
2612-02-4

5-methoxysalicylic acid

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
(i) SOCl2, Py, PE, (ii) H2, quinoline, sulfur, Pd-BaSO4, xylene; Multistep reaction;
tris(phenylthio)methane
4832-52-4

tris(phenylthio)methane

4-methoxy-phenol
150-76-5

4-methoxy-phenol

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
With dimethyl(methylthio)sulfonium tetrafluoroborate; water 1.) CH2Cl2, room temp., 2 h; Yield given. Multistep reaction;
N,N-diethyl-O-(4-methoxyphenyl)carbamate
85630-18-8

N,N-diethyl-O-(4-methoxyphenyl)carbamate

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

O-(2-formyl-4-methoxy)phenyl N,N-diethylcarbamate
85630-27-9

O-(2-formyl-4-methoxy)phenyl N,N-diethylcarbamate

Conditions
ConditionsYield
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
98751-26-9

2-t-butoxy-5-methoxybenzaldehyde

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid
2-Acetoxy-benzoic acid 2-formyl-4-methoxy-phenyl ester

2-Acetoxy-benzoic acid 2-formyl-4-methoxy-phenyl ester

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With hydroxide In 1,4-dioxane; water at 37℃; Rate constant; Thermodynamic data; var. temp., ΔH(excit.), ΔS)(excit.);
4-methoxy-phenol
150-76-5

4-methoxy-phenol

paraformaldehyde

paraformaldehyde

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
With ethylmagnesium bromide; triethylamine 1.) THF, RT, 20 min, 2.) C6H6, reflux, 2.5 h; Yield given. Multistep reaction;
2-acetoxy-5-methoxybenzaldehyde
62536-85-0

2-acetoxy-5-methoxybenzaldehyde

alkali

alkali

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

acetic acid
64-19-7

acetic acid

2-iodo-5-methoxybenzaldehyde
77287-58-2

2-iodo-5-methoxybenzaldehyde

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

2-oxy-phenylacetate sodium

2-oxy-phenylacetate sodium

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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
meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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
4-methoxy-phenol
150-76-5

4-methoxy-phenol

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

Hg

Hg

2-(2-hydroxy-5-methoxyphenyl)-4-phenoxymethyl-1,3-dioxolane
1079921-21-3

2-(2-hydroxy-5-methoxyphenyl)-4-phenoxymethyl-1,3-dioxolane

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

1-phenoxy-2,3-propanediol
538-43-2

1-phenoxy-2,3-propanediol

Conditions
ConditionsYield
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
1079921-26-8

2-(2-hydroxy-5-methoxyphenyl)-5-phenyl-1,3-dioxane

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

2-phenylpropane-1, 3-diol
1570-95-2

2-phenylpropane-1, 3-diol

Conditions
ConditionsYield
With water In methanol at 20℃; Quantum yield; Irradiation;A n/a
B 59 %Chromat.
2-(2-hydroxy-5-methoxyphenyl)-1,3-dioxolane
773101-17-0

2-(2-hydroxy-5-methoxyphenyl)-1,3-dioxolane

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

ethylene glycol
107-21-1

ethylene glycol

Conditions
ConditionsYield
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
1079921-29-1

2-(2-hydroxy-5-methoxyphenyl)-5,5-dimethyl-1,3-dioxane

A

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

B

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

Conditions
ConditionsYield
With water In methanol at 20℃; Quantum yield; Irradiation;A n/a
B 100 %Spectr.
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-methoxy-2-(trimethylsilyl)phenyl triflate

4-methoxy-2-(trimethylsilyl)phenyl triflate

A

2-Hydroxy-4-methoxybenzaldehyde
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

B

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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
ethanol
64-17-5

ethanol

4-methoxy-phenol
150-76-5

4-methoxy-phenol

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
With chloroform; potassium hydroxide In water at 60℃; for 15h; Reimer-Tiemann Phenol Formylation;
4-methoxy-phenol
150-76-5

4-methoxy-phenol

polyformaldehyde

polyformaldehyde

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
With magnesium chloride In acetonitrile Reflux;
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

1-hydroxy-4-methoxy-2-methylbenzene
5307-05-1

1-hydroxy-4-methoxy-2-methylbenzene

Conditions
ConditionsYield
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
672-13-9

2-hydroxy-5-methoxybenzaldehyde

acrylonitrile
107-13-1

acrylonitrile

6-methoxy-2H-chromene-3-carbonitrile
57543-71-2

6-methoxy-2H-chromene-3-carbonitrile

Conditions
ConditionsYield
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
672-13-9

2-hydroxy-5-methoxybenzaldehyde

allyl bromide
106-95-6

allyl bromide

2-allyloxy-5-methoxybenzaldehyde
71186-59-9

2-allyloxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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
672-13-9

2-hydroxy-5-methoxybenzaldehyde

propargyl bromide
106-96-7

propargyl bromide

5-methoxy-2-(prop-2-yn-1-yloxy)benzaldehyde
224317-65-1

5-methoxy-2-(prop-2-yn-1-yloxy)benzaldehyde

Conditions
ConditionsYield
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
672-13-9

2-hydroxy-5-methoxybenzaldehyde

benzyl bromide
100-39-0

benzyl bromide

2-benzyloxy-5-methoxybenzaldehyde
56979-57-8

2-benzyloxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
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%
9-ethyl-3-[(E)-2-nitrovinyl]-9H-carbazole

9-ethyl-3-[(E)-2-nitrovinyl]-9H-carbazole

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

9-ethyl-3-(6-methoxy-3-nitro-2H-chromen-2-yl)-9H-carbazole

9-ethyl-3-(6-methoxy-3-nitro-2H-chromen-2-yl)-9H-carbazole

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 70℃; for 0.5h;100%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

4-methoxy-2-[(5-methyl-3-isoxazolyl)imino]methylphenol
415715-07-0

4-methoxy-2-[(5-methyl-3-isoxazolyl)imino]methylphenol

Conditions
ConditionsYield
Reflux;100%
In ethanol for 2h; Reflux;90%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

{(1R,3R,4S,6S)-4-amino-4,7,7-trimethylbicyclo[4.1.0]heptan-3-yl}methanol
654680-82-7

{(1R,3R,4S,6S)-4-amino-4,7,7-trimethylbicyclo[4.1.0]heptan-3-yl}methanol

2-[(1S,3S,4R,6R)-4-hydroxymethyl-3,7,7-trimethylbicyclo[4.1.0]heptan-3-yliminomethyl]-4-methoxyphenol

2-[(1S,3S,4R,6R)-4-hydroxymethyl-3,7,7-trimethylbicyclo[4.1.0]heptan-3-yliminomethyl]-4-methoxyphenol

Conditions
ConditionsYield
In methanol at 20℃; for 24h;100%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

2-hydroxy-5-methoxybenzyl alcohol
41951-76-2

2-hydroxy-5-methoxybenzyl alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; for 1h;99.7%
With sodium tetrahydroborate85%
With sodium tetrahydroborate In ethanol at 20℃; Cooling with ice;85%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

diethyl malonate
105-53-3

diethyl malonate

6-methoxycoumarin-3-carboxylic acid
35924-44-8

6-methoxycoumarin-3-carboxylic acid

Conditions
ConditionsYield
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
672-13-9

2-hydroxy-5-methoxybenzaldehyde

prenyl bromide
870-63-3

prenyl bromide

5-methoxy-2-(3-methylbut-2-enyloxy)benzaldehyde
139579-42-3

5-methoxy-2-(3-methylbut-2-enyloxy)benzaldehyde

Conditions
ConditionsYield
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
672-13-9

2-hydroxy-5-methoxybenzaldehyde

N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

trifluoro-methanesulfonic acid 2-formyl-4-methoxy-phenyl ester
424788-79-4

trifluoro-methanesulfonic acid 2-formyl-4-methoxy-phenyl ester

Conditions
ConditionsYield
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
672-13-9

2-hydroxy-5-methoxybenzaldehyde

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

toluene-4-sulfonic acid 2-formyl-4-methoxy-phenyl ester
329235-34-9

toluene-4-sulfonic acid 2-formyl-4-methoxy-phenyl ester

Conditions
ConditionsYield
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
672-13-9

2-hydroxy-5-methoxybenzaldehyde

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2-tert-butyldimethylsiloxy-5-methoxyphenyl carboxaldehyde
441068-94-6

2-tert-butyldimethylsiloxy-5-methoxyphenyl carboxaldehyde

Conditions
ConditionsYield
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%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

malononitrile
109-77-3

malononitrile

2-(2-Amino-3-cyano-6-methoxy-4H-chromen-4-yl)-malononitrile

2-(2-Amino-3-cyano-6-methoxy-4H-chromen-4-yl)-malononitrile

Conditions
ConditionsYield
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℃;
O-Merrifield resin-bound 4-(2\-acetoacetylethyl)phenol

O-Merrifield resin-bound 4-(2\-acetoacetylethyl)phenol

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

3-acetyl-6-methoxycoumarin
13252-80-7

3-acetyl-6-methoxycoumarin

Conditions
ConditionsYield
With piperidine In ethanol for 2.5h; Knoevenagel condensation; Heating;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

ethyl 4-(2-formyl-4-methoxyphenoxy)butanoate
356039-75-3

ethyl 4-(2-formyl-4-methoxyphenoxy)butanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 1h;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

ethyl 5-bromovalerate
14660-52-7

ethyl 5-bromovalerate

ethyl 5-(2-formyl-4-methoxyphenoxy)pentanoate

ethyl 5-(2-formyl-4-methoxyphenoxy)pentanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 1h;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

benzoyl chloride
98-88-4

benzoyl chloride

2-formyl-4-methoxyphenyl benzoate

2-formyl-4-methoxyphenyl benzoate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

2-formyl-4-methoxyphenyl 4-bromobenzoate

2-formyl-4-methoxyphenyl 4-bromobenzoate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

2-formyl-4-methoxyphenyl 4-methoxybenzoate

2-formyl-4-methoxyphenyl 4-methoxybenzoate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

(E)-5-methoxy-2-hydroxybenzaldehyde oxime
66384-65-4

(E)-5-methoxy-2-hydroxybenzaldehyde oxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol at 60℃; for 3h; Inert atmosphere;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

norbornene
498-66-8

norbornene

C15H18O3

C15H18O3

Conditions
ConditionsYield
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
672-13-9

2-hydroxy-5-methoxybenzaldehyde

C15H13N3O2

C15H13N3O2

6-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-one
263364-71-2

6-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-one

Conditions
ConditionsYield
With triethylamine In neat (no solvent) at 20℃; for 0.0833333h; Sonication;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

Cinnamyl bromide
4392-24-9

Cinnamyl bromide

2-allyloxy-5-methoxybenzaldehyde
71186-59-9

2-allyloxy-5-methoxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

4-hydroxy-1-methyl-2(1H)-quinolone
1677-46-9

4-hydroxy-1-methyl-2(1H)-quinolone

tributylphosphine
998-40-3

tributylphosphine

3-((2-hydroxy-5-methoxyphenyl)(tributylphosphonio)methyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-olate

3-((2-hydroxy-5-methoxyphenyl)(tributylphosphonio)methyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-olate

Conditions
ConditionsYield
With pyrrolidine; benzoic acid In tetrahydrofuran at 30℃; for 1h; Schlenk technique; Inert atmosphere;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

propylmaleimide
21746-40-7

propylmaleimide

D-alanine methyl ester hydrochloride
14316-06-4

D-alanine methyl ester hydrochloride

methyl (1R,3S,3aR,6aS)-3-(2-hydroxy-5-methoxyphenyl)-1-methyl-4,6-dioxo-5-propyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate

methyl (1R,3S,3aR,6aS)-3-(2-hydroxy-5-methoxyphenyl)-1-methyl-4,6-dioxo-5-propyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 125℃; for 0.5h; Microwave irradiation; Green chemistry; diastereoselective reaction;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

ethyl 2-amino-3-phenylpropanoate hydrochloride
3182-93-2

ethyl 2-amino-3-phenylpropanoate hydrochloride

ethyl (E)-2-((2-hydroxy-5-methoxybenzylidene)amino)-3-phenylpropanoate

ethyl (E)-2-((2-hydroxy-5-methoxybenzylidene)amino)-3-phenylpropanoate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 24h; Inert atmosphere;99%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

6-methoxycoumarin
17372-53-1

6-methoxycoumarin

Conditions
ConditionsYield
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%

2-Hydroxy-5-methoxybenzaldehyde Specification

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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