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591-31-1 Usage

Chemical Properties

clear pale yellow to yellow liquid

Uses

3-Methoxybenzaldehyde is used to prepare 3-(3-methoxy-phenyl)-1-phenyl-propenone by reaction with benzldehyde. It is used as an eluent for mono-13C isotopomers of vanillin in normal phase silica gel chromatography. It acts as an inhibitor of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism.

Synthesis Reference(s)

Synthetic Communications, 24, p. 2011, 1994 DOI: 10.1080/00397919408010209

General Description

m-Anisaldehyde has significant antifungal activity against Candida sp., including the azole-resistant strains.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.

Purification Methods

Wash it with saturated aqueous NaHCO3, then H2O, dry it with anhydrous MgSO4 and distil it under reduced pressure under N2. Store it under N2 in sealed glass ampoules. [Beilstein 8 IV 241.]

Check Digit Verification of cas no

The CAS Registry Mumber 591-31-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 1 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 591-31:
(5*5)+(4*9)+(3*1)+(2*3)+(1*1)=71
71 % 10 = 1
So 591-31-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O2/c1-10-8-4-2-3-7(5-8)6-9/h2-6H,1H3

591-31-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • TCI America

  • (A0478)  m-Anisaldehyde  >98.0%(GC)

  • 591-31-1

  • 25mL

  • 360.00CNY

  • Detail
  • TCI America

  • (A0478)  m-Anisaldehyde  >98.0%(GC)

  • 591-31-1

  • 100mL

  • 990.00CNY

  • Detail
  • TCI America

  • (A0478)  m-Anisaldehyde  >98.0%(GC)

  • 591-31-1

  • 500mL

  • 3,450.00CNY

  • Detail
  • Alfa Aesar

  • (A13962)  3-Methoxybenzaldehyde, 98%   

  • 591-31-1

  • 25g

  • 350.0CNY

  • Detail
  • Alfa Aesar

  • (A13962)  3-Methoxybenzaldehyde, 98%   

  • 591-31-1

  • 100g

  • 1087.0CNY

  • Detail
  • Alfa Aesar

  • (A13962)  3-Methoxybenzaldehyde, 98%   

  • 591-31-1

  • 500g

  • 3794.0CNY

  • Detail

591-31-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Methoxybenzaldehyde

1.2 Other means of identification

Product number -
Other names 3-Methoxybezaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:591-31-1 SDS

591-31-1Synthetic route

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With oxygen; perruthenate modified mesoporous silicate MCM-41 In toluene at 80℃; for 3h; Oxidation;100%
With Oxone; [Mn(NO3)2(2,3,5,6-tetra(2-pyridyl)pyrazine)(H2O)]; tetrabutylammomium bromide In dichloromethane at 20℃; Catalytic behavior; Reagent/catalyst;100%
With 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane periodate In acetonitrile for 10h; Heating;99%
1,1-diacetoxy-1-(3-methoxyphenyl)methane
59184-17-7

1,1-diacetoxy-1-(3-methoxyphenyl)methane

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With sulphated zirconia In acetonitrile at 60℃; for 1h; Microwave irradiation;100%
With (NH4)3PW12O40 In methanol at 20℃; for 1h;93%
With poly(4-vinylpyridinium) hydrogen sulfate solid acid In methanol at 20℃; for 0.966667h; Irradiation;92%
m-anisoyl chloride
1711-05-3

m-anisoyl chloride

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With polymethylhydrosiloxane; trifuran-2-yl-phosphane; tetrabutyl ammonium fluoride; potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water at 20℃; for 1h;98%
With palladium; xylene at 140 - 150℃; Hydrogenation;
With sodium tris(tert-butoxo)aluminium hydride In tetrahydrofuran; diethylene glycol dimethyl ether at -78℃; for 3h; Yield given;
Stage #1: m-anisoyl chloride With aluminium hydride In tetrahydrofuran at 20℃; for 1h; Metallation;
Stage #2: With pyridinium chlorochromate In tetrahydrofuran; dichloromethane at 20℃; for 3h; Oxidation;
97 % Chromat.
(3-Methoxy-benzyloxy)-trimethyl-silane
132816-03-6

(3-Methoxy-benzyloxy)-trimethyl-silane

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With aluminium trichloride; tetramethylammonium chlorochromate In acetonitrile for 1.08333h; Heating;98%
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.166667h; Heating;96%
With aluminium trichloride; benzyltriphenylphosphonium chlorochromate In acetonitrile for 0.75h; Heating;95%
3-methoxybenzaldehyde phenylhydrazone

3-methoxybenzaldehyde phenylhydrazone

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.1h; Heating;98%
With quinolinium monofluorochromate(VI) In dichloromethane at 20℃; for 0.8h;93%
With cetyltrimethylammonium peroxodisulphate In acetonitrile for 0.333333h; Reflux;93%
m-methoxybenzyl chloride
824-98-6

m-methoxybenzyl chloride

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; for 0.05h; Microwave irradiation;98%
With 4-methylmorpholine N-oxide; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride; potassium iodide at 100℃; for 0.0333333h; Microwave irradiation; Ionic liquid;92%
With sodium nitrate; acetic acid In water for 7.5h; Reflux;81%
N-tert-butyl-1-(3-methoxyphenyl)methanimine
82632-37-9

N-tert-butyl-1-(3-methoxyphenyl)methanimine

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
Stage #1: N-tert-butyl-1-(3-methoxyphenyl)methanimine With chromium dichloride In tetrahydrofuran at 25℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: With phenylmagnesium bromide In tetrahydrofuran at 25℃; for 5h; Schlenk technique; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 25℃; for 3h; Schlenk technique; Inert atmosphere; regioselective reaction;
98%
With water
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

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

N,N-dimethyl-formamide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
Stage #1: 3-methoxyphenyl bromide With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at 0 - 5℃; for 1h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 1h; Further stages.;
96%
Ambient temperature; Mg anode, Cd coated catode, Bu4NBr electrolyte;56%
Stage #1: 3-methoxyphenyl bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 0℃;
2-(3-methoxyphenyl)-1,3-dioxolane
19693-78-8

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

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate In dichloromethane for 0.05h; Irradiation;96%
With aluminium trichloride; 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate for 0.00833333h;96%
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile at 20℃; for 0.25h;94%
With potassium dichromate; aluminium trichloride for 0.0833333h;90%
With K5 In acetone for 0.166667h; Heating;97 % Chromat.
carbon monoxide
201230-82-2

carbon monoxide

3-methoxyphenyl sulfurofluoridate

3-methoxyphenyl sulfurofluoridate

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With pyridine; 1,3-bis-(diphenylphosphino)propane; hydrogen; palladium diacetate In dimethyl sulfoxide at 120℃; under 7500.75 Torr; for 2h; Flow reactor;96%
3-methoxybenzaldehyde oxime
38489-80-4

3-methoxybenzaldehyde oxime

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With aluminium trichloride; benzyltriphenylphosphonium chlorochromate In acetonitrile for 0.666667h; Heating;95%
With potassium permanganate; 1-n-butyl-3-methylimidazolim bromide at 20℃; for 0.7h; Ionic liquid; chemoselective reaction;94%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 0.666667h; Heating;90%
2-[(3-methoxyphenyl)methylene]hydrazinecarboxamide

2-[(3-methoxyphenyl)methylene]hydrazinecarboxamide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With NTPPPODS In water; acetonitrile for 0.25h; Reflux;95%
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.166667h; Heating;94%
With quinolinium monofluorochromate(VI) In acetonitrile for 3h; Heating;93%
(E)-1-(3-methoxyphenyl)-N-phenylmethanimine
17637-72-8

(E)-1-(3-methoxyphenyl)-N-phenylmethanimine

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With hydrogenchloride; water In diethyl ether; toluene at 20℃; for 2h; Inert atmosphere;95%
C15H16N2O4S
1448723-38-3

C15H16N2O4S

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
Stage #1: C15H16N2O4S With 1H-imidazole; 1-(Trimethylsilyl)imidazole In toluene at 55℃; McFadyen-Stevens Reaction;
Stage #2: With citric acid In methanol at 20℃; McFadyen-Stevens Reaction;
95%
Stage #1: C15H16N2O4S With 1H-imidazole; 1-(Trimethylsilyl)imidazole In toluene at 55℃; Inert atmosphere;
Stage #2: With citric acid In toluene at 23℃; Inert atmosphere;
95%
1-Methoxy-3-phenethyloxymethyl-benzene
121336-27-4

1-Methoxy-3-phenethyloxymethyl-benzene

A

2-phenylethanol
60-12-8

2-phenylethanol

B

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 24h;A 80%
B 94%
3-methoxylbenzyl azide
123767-44-2

3-methoxylbenzyl azide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With iron(III) chloride; dihydrogen peroxide In dichloromethane; water for 13h; Reflux; Air;94%
meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

methyl iodide
74-88-4

methyl iodide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 25 - 30℃; for 12h; Inert atmosphere;93%
With potassium carbonate In acetone for 3h; Reflux;92%
With potassium carbonate In N,N-dimethyl-formamide91%
formic acid
64-18-6

formic acid

3-methoxy-1-iodobenzene
766-85-8

3-methoxy-1-iodobenzene

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide; sodium phosphate at 105℃; for 3h; Green chemistry;93%
With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; dicyclohexyl-carbodiimide at 100℃; for 2h; Sealed tube;85%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 2h; Sealed tube;80%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube;79%
2-(3-methoxyphenyl)-1,3-dithiane
54308-43-9

2-(3-methoxyphenyl)-1,3-dithiane

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
Stage #1: 2-(3-methoxyphenyl)-1,3-dithiane With trichloroisocyanuric acid; silica gel at 20℃; for 0.05h;
Stage #2: With water at 20℃;
92%
With p-benzoquinone; sodium iodide In water; acetonitrile at 100℃; for 24h;91%
With eosin y In water; acetonitrile at 20℃; for 2h; Irradiation;91%
With tetrachlorosilane; dimethyl sulfoxide In dichloromethane at 20℃; for 0.75h;90%
With water In 1,4-dioxane at 100℃; for 48h; Inert atmosphere;74%
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-octane-1-sulfonic acid 4-formyl-2-methoxy-phenyl ester
689247-71-0

1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-octane-1-sulfonic acid 4-formyl-2-methoxy-phenyl ester

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With formic acid; potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; acetone; toluene at 100℃; for 0.333333h; microwave irradiation;92%
2-(3-methoxy-phenyl)-[1,3]oxathiolane

2-(3-methoxy-phenyl)-[1,3]oxathiolane

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate at 90℃; for 0.133333h;92%
ethyl 3-methoxythiobenzoate
28145-59-7

ethyl 3-methoxythiobenzoate

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With triethylsilane; palladium on activated charcoal In acetone at 20℃;91%
With triethylsilane; palladium on activated charcoal In tetrahydrofuran at 20℃; for 5h; Fukuyama reduction;90%
With triethylsilane; palladium on activated charcoal In acetone Ambient temperature; Yield given;
3-methoxystyrene
626-20-0

3-methoxystyrene

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With eosin Y; oxygen In dimethyl sulfoxide at 20℃; for 9h; Irradiation; Green chemistry;91%
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In 1,2-dichloro-ethane at 70℃; under 760.051 Torr; for 6h; Green chemistry; chemoselective reaction;78%
meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

dimethyl sulfate
77-78-1

dimethyl sulfate

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In acetone for 0.0833333h; Etherification; methylation; microwave irradiation;90%
With sodium hydroxide
With sodium hydroxide
2-(3-methoxybenzyloxy)tetrahydro-2H-pyran
18483-97-1

2-(3-methoxybenzyloxy)tetrahydro-2H-pyran

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With dipotassium peroxodisulfate; molybdenum trioxide In water; acetonitrile for 0.34h; Reflux;90%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 0.5h; Heating;88%
With aluminium trichloride; benzyltriphenylphosphonium chlorochromate In acetonitrile for 0.5h; Heating;88%
sodium; hydroxy-(3-methoxy-phenyl)-methanesulfonate

sodium; hydroxy-(3-methoxy-phenyl)-methanesulfonate

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With Montmorillonite KSF clay for 0.00277778h; Elimination; microwave irradiation;90%
1-(3-Methoxyphenyl)ethanone
586-37-8

1-(3-Methoxyphenyl)ethanone

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With copper(l) iodide; oxygen In dimethyl sulfoxide at 120℃; for 26h; chemoselective reaction;90%
5-[(3-methoxyphenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione
6258-45-3

5-[(3-methoxyphenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With oxone In water; acetonitrile at 45℃; for 1h;90%
N-(2-cyanoethyl) N-(3-methoxybenzyl)-4-methylaniline
127598-74-7

N-(2-cyanoethyl) N-(3-methoxybenzyl)-4-methylaniline

A

3-(2-Dimethylaminomethyl-4-methyl-phenylamino)-propionitrile
118072-35-8

3-(2-Dimethylaminomethyl-4-methyl-phenylamino)-propionitrile

B

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With water; trichlorophosphate In N,N-dimethyl-formamide Vilsmeier reaction;A 80%
B 89%
2-(4-methoxyphenyl)-1,3-dithiane
24588-72-5

2-(4-methoxyphenyl)-1,3-dithiane

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Conditions
ConditionsYield
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 3h; Heating;89%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

methylamine
74-89-5

methylamine

N-(3-methoxybenzylidene)methanamine
16928-30-6

N-(3-methoxybenzylidene)methanamine

Conditions
ConditionsYield
at 20℃; for 12h;100%
In ethanol at 0 - 40℃;90%
In water for 10h; Ambient temperature;86%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

3-methoxybenzyl alcohol
6971-51-3

3-methoxybenzyl alcohol

Conditions
ConditionsYield
With hydrogen; Pd as electrode electrochemical reaction;100%
With sodium tetrahydroborate In methanol at 20℃; for 1h;100%
With sodium tetrahydroborate; Dowex1-x8 In tetrahydrofuran at 20℃; for 0.5h;99%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

ethyl (E)-3-(3-methoxyphenyl)acrylate
33877-04-2, 24393-55-3

ethyl (E)-3-(3-methoxyphenyl)acrylate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With lithium chloride In tetrahydrofuran at 20℃; for 0.25h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
100%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h;100%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30℃; for 4h; Glovebox;98%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

bis(3-methoxyphenyl)methanol
55360-45-7

bis(3-methoxyphenyl)methanol

Conditions
ConditionsYield
With n-butyllithium In hexane; ethyl acetate100%
With magnesium In diethyl ether for 1h; Ambient temperature;62%
With magnesium 1.) ether, ultrasound; Yield given. Multistep reaction;
Stage #1: 3-methoxyphenyl bromide With magnesium In tetrahydrofuran at 0℃; Reflux; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
Stage #3: With hydrogenchloride; water In tetrahydrofuran
Stage #1: 3-methoxyphenyl bromide With magnesium In diethyl ether at 20℃; for 2h; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde In diethyl ether at 20℃; for 2h; Inert atmosphere;
carbon tetrabromide
558-13-4

carbon tetrabromide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

1,1-dibromo-2-(3-methoxyphenyl)ethene
253684-23-0

1,1-dibromo-2-(3-methoxyphenyl)ethene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane100%
With triphenylphosphine In dichloromethane at 0℃; for 5.25h; Inert atmosphere;96%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde In dichloromethane at 0℃; for 1.08333h; Inert atmosphere;
94%
potassium cyanide
151-50-8

potassium cyanide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

m-methoxymandelonitrile
53313-94-3

m-methoxymandelonitrile

Conditions
ConditionsYield
Stage #1: 3-methoxy-benzaldehyde With hydrogenchloride; sodium sulfite In tetrahydrofuran; water at 20℃; for 0.166667h;
Stage #2: potassium cyanide In tetrahydrofuran; water for 0.5h;
100%
With sodium hydrogensulfite 1) H2O, 40 deg C, 0.5 h, 2) H2O, 0 deg C, 1 h; Multistep reaction;
With acetic acid In water
With hydrogenchloride; sodium sulfite In tetrahydrofuran at 20℃; for 0.5h;
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

acetone
67-64-1

acetone

(E)-4-(3-methoxyphenyl)but-3-en-2-one
20766-31-8, 30625-53-7

(E)-4-(3-methoxyphenyl)but-3-en-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 25℃; for 5h;100%
With 1-n-butyl-3-methylimidazolim bromide at 60℃; for 6h; Aldol condensation; Enzymatic reaction;87%
With sodium hydroxide for 1.66667h;83%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

methylamine
74-89-5

methylamine

1-(3-methoxyphenyl)-N-methylmethanamine
41789-95-1

1-(3-methoxyphenyl)-N-methylmethanamine

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; water at 0℃; for 2h;100%
With sodium tetrahydroborate In methanol; water at 0 - 20℃;99%
Stage #1: 3-methoxy-benzaldehyde; methylamine In methanol; water at 0 - 20℃; for 15.3333h;
Stage #2: With sodium tetrahydroborate In methanol; 20C at 0 - 20℃; for 2 - 3h; Product distribution / selectivity;
29%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

N'-(3-methoxybenzylidene)-4-methylbenzen sulfonohydrazide
19350-71-1

N'-(3-methoxybenzylidene)-4-methylbenzen sulfonohydrazide

Conditions
ConditionsYield
In ethanol for 8h; Reflux;100%
With polystyrene sulfonic acid In water at 100℃; for 0.0833333h; Wavelength; Reagent/catalyst; Solvent; Temperature; Microwave irradiation; Green chemistry;92%
In methanol at 20℃; for 3h;90%
diethylzinc
557-20-0

diethylzinc

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

(1S)-1-(3-methoxyphenyl)propan-1-ol
134677-28-4

(1S)-1-(3-methoxyphenyl)propan-1-ol

Conditions
ConditionsYield
(1S)-1-(9-piperidylfluoren-9-yl)ethanol In hexane; toluene at 0℃; for 4h; Addition;100%
Stage #1: diethylzinc In toluene at 0℃; for 0.5h;
Stage #2: 3-methoxy-benzaldehyde In toluene at 0 - 20℃; for 48h; Reagent/catalyst; enantioselective reaction;
99%
With (3S,4S)-2,2-dimethyl-4-[N-(9'-phenylfluoren-9'-yl)amino]pentan-3-ol In hexane; toluene at 18℃; for 1h; Addition;97%
diethylzinc
557-20-0

diethylzinc

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

1-(3-methoxyphenyl)propanol
52956-27-1

1-(3-methoxyphenyl)propanol

Conditions
ConditionsYield
With (R,R)-(2,4,6-Me3C6H2-CH=N-CH(Ph))2; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane 1.) -78 deg C, 4 h, 2.) -20 deg, 1 h;100%
With (1R,2R)-N,N'-bis[(2,4,6-trimethylphenyl)methylene]-1,2-cyclohexane-diamine; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane at -78 - -20℃; for 5h;100%
Stage #1: diethylzinc With titanium(IV) isopropylate; (1R,2R)-1,2-bis(3,5-dibromophenyl)ethane-1,2-diol In hexane; dichloromethane at 25℃; for 0.333333h; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde In hexane; dichloromethane at 0℃; for 24h; Reagent/catalyst; Inert atmosphere;
53%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

m-anisaldehyde dimethyl acetal
59276-28-7

m-anisaldehyde dimethyl acetal

Conditions
ConditionsYield
In methanol at 20℃; for 1h; Inert atmosphere;100%
With ytterbium(III) chloride hexahydrate In methanol at 20℃; for 18h;98%
With toluene-4-sulfonic acid In methanol at 20℃; for 1h; Inert atmosphere; Sealed tube;93%
(R)-2-methoxy-1-phenylethylamine
64715-85-1, 91298-74-7, 127180-88-5

(R)-2-methoxy-1-phenylethylamine

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

((R)-2-Methoxy-1-phenyl-ethyl)-[1-(3-methoxy-phenyl)-meth-(E)-ylidene]-amine

((R)-2-Methoxy-1-phenyl-ethyl)-[1-(3-methoxy-phenyl)-meth-(E)-ylidene]-amine

Conditions
ConditionsYield
In toluene Heating;100%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Ethyl isobutyrate
97-62-1

Ethyl isobutyrate

ethyl 3-hydroxy-3-(3-methoxyphenyl)-2,2-dimethylpropanoate
602304-70-1, 293769-53-6

ethyl 3-hydroxy-3-(3-methoxyphenyl)-2,2-dimethylpropanoate

Conditions
ConditionsYield
Stage #1: Ethyl isobutyrate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 3-methoxy-benzaldehyde In tetrahydrofuran at -78℃; for 1.5h;
100%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(3-methoxyphenyl)-acetonitrile

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(3-methoxyphenyl)-acetonitrile

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether; chiral salen-based titanium In dichloromethane at -40℃; for 24h;100%
With 3,3'-di-naphthalen-2-yl-biphenyl-2,2'-diol; titanium(IV) isopropylate; quinindine; isopropyl alcohol In toluene at -20℃; for 7h; Strecker reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
With chiral [(salen)TiO]2 In dichloromethane at -40℃; for 17h;94%
With chiral bimetallic titanium(salen) In dichloromethane at -40℃; for 17h;94%
With potassium cyanide; 18-crown-6 ether; titanium(salen) complex In dichloromethane at -40℃; for 24h;
4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

3,3'-((3-methoxyphenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)
10172-74-4

3,3'-((3-methoxyphenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)

Conditions
ConditionsYield
With 4-sulfophthalic acid In water at 80℃; for 0.333333h; Catalytic behavior; Green chemistry;100%
With piperidine In ethanol at 20℃; for 4h;98%
With 4-aminobenzene sulfonic acid In water at 80℃; for 0.366667h; Green chemistry;96%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

1-amino-2-propene
107-11-9

1-amino-2-propene

N-[(3-methoxyphenyl)methylidene]-N-(2-propenyl)amine
246509-60-4

N-[(3-methoxyphenyl)methylidene]-N-(2-propenyl)amine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 20h;100%
With magnesium sulfate In dichloromethane for 1h; Heating;95%
potassium cyanide

potassium cyanide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

m-methoxymandelonitrile
53313-94-3

m-methoxymandelonitrile

Conditions
ConditionsYield
With hydrogenchloride; sodium sulfite In tetrahydrofuran; water at 20℃; for 0.666667h;100%
butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

2-(3-methoxy-phenyl)-4,5-dimethyl-oxazole-3-oxide

2-(3-methoxy-phenyl)-4,5-dimethyl-oxazole-3-oxide

Conditions
ConditionsYield
Stage #1: butane-2,3-dione mono-oxime; 3-methoxy-benzaldehyde With hydrogenchloride; acetic acid In toluene at 22℃; for 16h;
Stage #2: With sodium hydroxide In water; toluene at 32℃; pH=10.6;
100%
tert-butyl 1-(2-methylallyl)hydrazinecarboxylate
1005794-49-9

tert-butyl 1-(2-methylallyl)hydrazinecarboxylate

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

tert-butyl 2-(3-methoxybenzylidene)-1-(2-methylallyl)hydrazinecarboxylate

tert-butyl 2-(3-methoxybenzylidene)-1-(2-methylallyl)hydrazinecarboxylate

Conditions
ConditionsYield
In ethanol at 20℃;100%
tert-butylamine
75-64-9

tert-butylamine

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

N-tert-butyl-1-(3-methoxyphenyl)methanimine
82632-37-9

N-tert-butyl-1-(3-methoxyphenyl)methanimine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 4h;100%
With titanium tetrachloride In diethyl ether; toluene at 0℃; for 0.25h; Glovebox; Inert atmosphere; Schlenk technique;93%
at 100℃; for 4h;86%
dimethyl <2-(tert-butyldimethylsilyl)-2-oxoethyl>-phosphonate
120943-70-6

dimethyl <2-(tert-butyldimethylsilyl)-2-oxoethyl>-phosphonate

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

(E)-1-(tert-butyldimethylsilyl)-3-(3-methoxyphenyl)prop-2-en-1-one
1204324-78-6

(E)-1-(tert-butyldimethylsilyl)-3-(3-methoxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
Stage #1: dimethyl <2-(tert-butyldimethylsilyl)-2-oxoethyl>-phosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; Horner-Wadsworth-Emmons olefination; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde In tetrahydrofuran at 20℃; for 15h; Horner-Wadsworth-Emmons olefination; Inert atmosphere;
100%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

C12H17NO2Si

C12H17NO2Si

Conditions
ConditionsYield
Stage #1: trimethylsilyl cyanide; 3-methoxy-benzaldehyde; (S,S,S)-[Ru(2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)bis(phenylglycinate)] In tetrahydrofuran; tert-butyl methyl ether at -78℃; for 0.166667h; Inert atmosphere;
Stage #2: lithium chloride In tetrahydrofuran; tert-butyl methyl ether at -78℃; for 3h; Product distribution / selectivity; Inert atmosphere;
100%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

4-methoxycarbonyl aniline
619-45-4

4-methoxycarbonyl aniline

4-[(3-methoxy-benzylidene) amino]-benzoic acid methyl ester
349456-93-5

4-[(3-methoxy-benzylidene) amino]-benzoic acid methyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 12h; Reflux;100%
In N,N-dimethyl-formamide at 100 - 150℃;
N-(4-chlorophenyl)-2,2-dimethylpropionamide
65854-91-3

N-(4-chlorophenyl)-2,2-dimethylpropionamide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

N-{4-chloro-2-[hydroxy(3-methoxyphenyl)methyl]-phenyl}-2,2-dimethylpropanamide
1292850-39-5

N-{4-chloro-2-[hydroxy(3-methoxyphenyl)methyl]-phenyl}-2,2-dimethylpropanamide

Conditions
ConditionsYield
Stage #1: N-(4-chlorophenyl)-2,2-dimethylpropionamide With sec.-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 2h;
Stage #2: 3-methoxy-benzaldehyde In tetrahydrofuran; hexane at 0℃; for 0.5h;
100%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

[(3-methoxyphenyl)methylidene]hydrazine
108087-83-8

[(3-methoxyphenyl)methylidene]hydrazine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 20℃; Cooling;100%
With hydrazine hydrate In methanol at 20℃; for 1h;99%
With hydrazine hydrate In methanol at 20℃; for 1h;99%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

methylamine
74-89-5

methylamine

2-(3-methoxyphenyl)-2-(methylamino)acetonitrile

2-(3-methoxyphenyl)-2-(methylamino)acetonitrile

Conditions
ConditionsYield
Stage #1: 3-methoxy-benzaldehyde; methylamine In methanol; water for 1h;
Stage #2: trimethylsilyl cyanide In methanol; water at 20℃; for 24h;
100%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

p-aminoethylbenzoate
94-09-7

p-aminoethylbenzoate

4-[(3-methoxy-benzylidene) amino]-benzoic acid methyl ester
349456-93-5

4-[(3-methoxy-benzylidene) amino]-benzoic acid methyl ester

Conditions
ConditionsYield
toluene-4-sulfonic acid In toluene for 12h; Reflux;100%

591-31-1Relevant articles and documents

Microwave Assisted Oxidation of Benzyl Halides to Aldehydes and Ketones with 4-Hydroxypyridinium Nitrate Functionalized Silica Gel in Aqueous Media

Ghalehbandi, Shermineh sadat,Ghazanfari, Dadkhoda,Ahmadi, Sayed Ali,Sheikhhosseini, Enayatollah

, p. 176 - 183 (2021/04/29)

-

Zirconium-based metal-organic framework as an efficiently heterogeneous photocatalyst for oxidation of benzyl halides to aldehydes

Xue, Ping,Huang, Jiming,Lin, Liguang,Li, Rong,Tang, Mi,Wang, Zhengbang

, (2021/04/12)

The development of efficient heterogeneous catalysts for fine chemical synthesis is critical for practical applications. Herein, for the first time, the zirconium-based metal-organic framework (UiO-66-NH2) is applied as an efficiently heterogeneous photocatalyst for conversion of benzyl halides to corresponding aldehydes with high selectivity (about 80 %) and conversion (up to 99 %) in the presence of oxygen and DMF as solvent. Through a series of experiments and analysis, the reaction mechanism is proposed to involve nucleophilic attack of the N-oxide. This study provides a general, environmental and high selective method to prepare benzaldehydes and broadens the application fields of UiO-66-NH2.

Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls

Li, Xue,Bai, Fang,Liu, Chaogan,Ma, Xiaowei,Gu, Chengzhi,Dai, Bin

supporting information, p. 7445 - 7449 (2021/10/02)

An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.

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