620-23-5

Basic information

• Product Name: m-Tolualdehyde
• Synonyms: 3-METHYLBENZALDEHYDE (STABILISED WITH HY;m-Tolualdehyde, 3-Formyltoluene;m-Tolualdehyde(stabilized with HQ);620-23-5;m-Tolualdehyde 97%;3-Methylbenzaldehyde (stabilised with hydroquinone) for synthesis;3-methyl-benzaldehyd;Benzaldehyde, 3-methyl-
• CAS NO: 620-23-5
• Molecular Formula: C₈H₈O
• Molecular Weight: 120.15
• EINECS: 210-632-0
• Product Categories: Chemical Synthesis;Organic Building Blocks;Benzene derivatives;Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Building Blocks;C8;Carbonyl Compounds
• Mol File: 620-23-5.mol
• Article Data: 351

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 199 °C(lit.)
• Flash Point: 173 °F
• Appearance: colorless to brownish-yellow/Liquid
• Density: 1.019 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.541(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: slightly soluble
• Sensitive: Air Sensitive
• BRN: 741964
• CAS DataBase Reference: m-Tolualdehyde(CAS DataBase Reference)
• NIST Chemistry Reference: m-Tolualdehyde(620-23-5)
• EPA Substance Registry System: m-Tolualdehyde(620-23-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 23-24/25-37/39-26-22
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• RTECS: CU7033700
• F: 10-23
• TSCA: T
• HazardClass: AIR SENSITIVE
• Hazardous Substances Data: 620-23-5(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to brownish liquid

Uses

Different sources of media describe the Uses of 620-23-5 differently. You can refer to the following data:
1. m-Tolualdehyde is an aromatic aldehyde used as a fragrance agent in food and cosmetics. 3-Methylbenzaldehyde is also used as a reagent in the preparation of a wide range of pharmaceutical compou nds such as anti-inflammatory agents.
2. m-Tolualdehyde is used as a fragrance agent in food and cosmetics. It is also used as a reagent in the preparation of a wide range of pharmaceutical compounds such as anti-inflammatory agents.

Definition

ChEBI: A tolualdehyde compound with the methyl substituent at the 3-position.

InChI:InChI=1/C8H8O/c1-7-3-2-4-8(5-7)6-9/h2-6H,1H3

Synthetic route

carbon monoxide (201230-82-2) + 3-Iodotoluene (625-95-6) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With triethylsilane; palladium diacetate; sodium hydrogencarbonate; sodium carbonate at 20℃; under 760.051 Torr; for 48h;	90%
With rhodium(III) chloride trihydrate; hydrogen; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 90℃; under 7500.75 Torr; for 12h; Autoclave;	90%
With sodium formate In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 5h;	86%
With sodium formate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 10h;	84%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 110℃; under 66195.7 Torr; for 2h;	68 % Chromat.

3-methylbenzaldehyde oxime (52707-50-3, 52707-55-8, 41977-54-2) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With N,N'-dichlorophenobarbital In acetonitrile at 20℃;	95%
With molybdenum(V) chloride; zinc In acetonitrile at 20℃; for 0.0833333h;	94%
With potassium permanganate; 1-n-butyl-3-methylimidazolim bromide at 20℃; for 1h; Ionic liquid; chemoselective reaction;	91%

1,1-diacetoxy-1-(3-methylphenyl)-methane (120158-57-8) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With sulphated zirconia In acetonitrile at 60℃; for 0.3h; Microwave irradiation;	100%
With sulfonated rice husk ash In acetonitrile at 60℃; for 0.0333333h;	91%
With saccharin sulfonic acid at 90℃; for 0.05h; Neat (no solvent);	90%

m-methylphenylacetic acid (621-36-3) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile at 25℃; for 10h; UV-irradiation;	92%
With potassium 12-tungstocobaltate(III) In water; acetonitrile for 0.166667h; Microwave irradiation;	90%
With dipotassium peroxodisulfate In water at 90℃; for 12h; Green chemistry;	80%
With oxygen; copper diacetate In dimethyl sulfoxide at 120℃; for 18h; Sealed tube;	71%
With iron(III) chloride; oxygen In N,N-dimethyl-formamide at 110℃;	67%

carbon dioxide (124-38-9) + 3-Iodotoluene (625-95-6) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry;	86%
With carbon supported Pd nanoparticles; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 80℃; under 7500.75 Torr; for 12h; Sealed tube; Green chemistry;	82%
With rhodium(III) iodide; hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave;	80%

formic acid (64-18-6) + 3-Iodotoluene (625-95-6) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube;	81%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 2h; Sealed tube;	77%
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; tricyclohexylphosphine In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;	67%

1-chloromethyl-3-methyl-benzene (620-19-9) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
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;	90%
With 4-methylmorpholine N-oxide In tetrahydrofuran at 20℃; for 12h; Reflux;	80%

3-methylbenzyl alcohol (587-03-1) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With iodosylbenzene; Cl-CH2-PS supported 5-amino-1,10-phenanthroline-Ru In acetonitrile at 60℃; for 2h;	100%
Stage #1: 3-methylbenzyl alcohol With iron(III) chloride hexahydrate; oxygen; silica gel In toluene for 0.0833333h; Autoclave; Stage #2: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In toluene at 80℃; under 3750.38 Torr; for 8h; Autoclave;	99%
With dihydrogen peroxide In water at 100℃; for 6.5h; chemoselective reaction;	99%

m-Toluic acid (99-04-7) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With dipotassium hydrogenphosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane; dimethyl dicarbonate In acetonitrile at 20℃; for 6h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;	90%
With potassium phosphate; sodium hypophosphite; 2,2-dimethylpropanoic anhydride; palladium diacetate; tricyclohexylphosphine In tetrahydrofuran at 60℃; for 16h;	73%
ueber <3-Methyl-α-phenylimino-benzyl>-phenyl-carbamidsaeure-aethylester;

3-Iodotoluene (625-95-6) + Glyoxilic acid (298-12-4) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 2,2'-azobis(isobutyronitrile); oxygen; triethylamine In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 4h; Schlenk technique; Sealed tube;	63%

3-Methylbenzonitrile (620-22-4) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With formic acid; platinum(IV) oxide In water at 55 - 60℃; for 3h;	92%
With C13H26B(1-)*K(1+) In tetrahydrofuran for 24h; Ambient temperature;	89%
With diisobutylaluminium hydride In diethyl ether at 20℃; for 5h;	76%

meta-bromotoluene (591-17-3) + Glyoxilic acid (298-12-4) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 2,2'-azobis(isobutyronitrile); oxygen; triethylamine In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 5h; Schlenk technique; Sealed tube;	52%

3-Methylbenzoyl chloride (1711-06-4) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With quinoline; Pd-BaSO4; xylene Hydrogenation;
With thexyl-s-butoxyborane In tetrahydrofuran at 25℃; for 120h; Yield given;
Multi-step reaction with 2 steps 1: 83 percent / pyridine / 0 °C 2: anhydrous potassium carbonate / methanol / 118 h / Heating View Scheme

3-methylbenzyl alcohol (587-03-1) → m-tolyl aldehyde (620-23-5) + m-Toluic acid (99-04-7)

Conditions	Yield
With tetra-n-butylammonium peroxomonosulfate In dichloromethane at 20℃; for 0.5h;
With oxygen In water at 80℃; under 760.051 Torr; for 8h;
With Oxone In water at 50℃; for 21h;
With potassium peroxymonosulfate sulfate; tetrabutylammomium bromide In water at 70℃; for 4h; Reagent/catalyst; Green chemistry;

1-bromomethyl-3-methyl-benzene (620-13-3) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With bis-{4-methoxy-phenyl}-selenoxyde; sodium hydrogencarbonate In acetonitrile at 75℃; for 5h;	93%
With potassium hydrogencarbonate; dimethyl sulfoxide for 0.05h; Microwave irradiation;	89%
With hexamethylenetetramine durch Behandeln mit Wasser oder verd. Alkohol;
Multi-step reaction with 3 steps 1: 99 percent / Na2CO3 2: 99 percent / permaleic acid 3: 1.) trifluoroacetic anhydride; 2.) NBS / 1.) 10 min, r.t.; 2.) 80percent CH3CN, 20 min, r.t. View Scheme
With hexamethylenetetramine durch Behandeln mit Wasser oder verd. Alkohol;

ethyl 3-methylbenzoate (120-33-2) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With sodium tris(diethylamino)aluminum hydride In tetrahydrofuran; dodecane at -78℃; for 24h;	89%
With lithium-tris(diethylamino)hydridoaluminate In tetrahydrofuran at -78℃; for 3h; Reduction;
With Na(1+)*C12H27AlNO5(1-) In tetrahydrofuran; toluene at 0 - 20℃; for 0.5h;	99 %Chromat.

carbon monoxide (201230-82-2) + meta-bromotoluene (591-17-3) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite In toluene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere;	89%
With poly-γ-(p-diphenylphosphinophenyl)propylsiloxane Pd; sodium acetate In N,N-dimethyl-formamide at 110℃; for 12h;	53%

3-methylstyrene (100-80-1) → 3-methylstyrene oxide (704898-29-3, 1195902-12-5) + m-tolyl aldehyde (620-23-5)

Conditions	Yield
With [Cu(2,2'-bipyridine)(2-hap)(ClO4)]; dihydrogen peroxide In acetonitrile at 60℃; for 8h;	A 85% B n/a
With tert.-butylhydroperoxide In acetonitrile at 65 - 68℃; for 24h;	A 63% B 23%
With tert.-butylhydroperoxide; Gd2(N3)(nic)2(OH)3(Hnic)(H2O) In acetonitrile at 68 - 70℃; for 24h;	A 60% B 35%

3,N,N-trimethylbenzamide (6935-65-5) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With lithium diisobutylmorpholinoaluminum hydride In tetrahydrofuran; hexane at 0℃; for 0.5h;	97 %Chromat.
With benzoic acid ethyl ester; copper diisobutyl-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 12h; Temperature; Solvent; Inert atmosphere; chemoselective reaction;	95 %Chromat.
With acetophenone In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;	33 %Chromat.

(E)-3,3'-dimethylstilbene (35286-92-1) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With iodine; oxygen; trifluoroacetic acid In methanol for 20h; Irradiation;	83%

m-xylene (108-38-3) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 2.5h; Irradiation; Green chemistry;	90%
With 1,4-bis(triphenylphosphonium)butane cerium nitrate In water; acetic acid for 0.5h; Reflux;	88%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 85℃; for 16h;	85%

3-methylbenzyl alcohol (587-03-1) + aniline (62-53-3) → N-(3-methylbenzylidene)aniline (6906-25-8) + N-(3-methylbenzyl)aniline (75366-13-1) + m-tolyl aldehyde (620-23-5)

Conditions	Yield
With PdAu alloy nanoparticles encapsulated inside MIL-100(Fe) cavities In acetonitrile for 24h; Irradiation; Inert atmosphere; Schlenk technique; Sealed tube;	A 14% B 77% C 36%
With Pd nanoparticles encapsulated inside a MIL100(Fe) cavity In acetonitrile for 24h; Sealed tube; Irradiation; Inert atmosphere;	A 16% B 62% C 24%

2-(m-tolyl)-1,3-dithiolane (82436-18-8) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With silica gel; ferric nitrate In hexane at 50℃; for 0.166667h;	98%
With indium (III) iodide; dihydrogen peroxide In water; toluene at 20℃; for 15h; Inert atmosphere; Sealed tube;	82 mg

carbon dioxide (124-38-9) + meta-bromotoluene (591-17-3) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With rhodium(III) iodide; dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave;	90%
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry;	76%

m-xylene (108-38-3) → 3-methylbenzyl alcohol (587-03-1) + m-tolyl aldehyde (620-23-5) + m-Toluic acid (99-04-7)

Conditions	Yield
With zinc(II) 1,8,15,22-tetrachlorophthalocyanine; C60H60BrFeN4; oxygen; nickel diacetate at 125℃; under 4500.45 - 7500.75 Torr; for 1.5h; Reagent/catalyst; Pressure; Temperature;
Stage #1: m-xylene at 220℃; under 18001.8 Torr; Stage #2: With water at 182℃; under 12001.2 Torr;
With [(copper(II))3(μ3-1κN3,2κN2O,3κN-N′-(di(pyridin-2-yl)methylene)pyrazine-2-carbohydrazide)(μ-nitrate)(nitrate)3(H2O)3]*(nitrate); dihydrogen peroxide In acetonitrile at 50℃; for 3h; Time; Reagent/catalyst; Microwave irradiation;	A 15.3 %Chromat. B 5.9 %Chromat. C 3.4 %Chromat.

1-(3'-methylphenyl)-1,2-dihydroxyethane (78649-50-0) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
With oxygen; sodium carbonate In water at 20℃; for 5h; Irradiation; Green chemistry;	79%

2-(3-methylphenyl)-1,3-dithiane (62381-20-8) → m-tolyl aldehyde (620-23-5)

Conditions	Yield
Stage #1: 2-(3-methylphenyl)-1,3-dithiane With trichloroisocyanuric acid; silica gel at 20℃; for 0.05h; Stage #2: With water at 20℃;	94%
With tetrachlorosilane; dimethyl sulfoxide In dichloromethane at 20℃; for 0.583333h;	93%

1-amino-3-(dimethylamino)propane (109-55-7) + m-tolyl aldehyde (620-23-5) → N-(3-methylbenzylidene)-N',N'-dimethyl-1,3-propanediamine

Conditions	Yield
In ethanol Heating;	100%
In benzene Heating;

propylamine + m-tolyl aldehyde (620-23-5) → N-(3-methylbenzylidene)propan-1-amine

Conditions	Yield
at 20℃; for 12h;	100%
In methanol at 25℃; Mechanism; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.), kinetic solvent isotope effect;
With sodium sulfate In dichloromethane for 2h;

diethylzinc (557-20-0) + m-tolyl aldehyde (620-23-5) → (S)-1-(3-methylphenyl)propan-1-ol (213267-92-6)

Conditions	Yield
(1S)-1-(9-piperidylfluoren-9-yl)ethanol In hexane; toluene at 0℃; for 4h; Addition;	100%
Stage #1: diethylzinc With 2,2'-(propane-2,2-diyl)bis(6,6-dimethyl-5,6,7,8-tetrahydro-5,7-methanoquinoline-8,2-diyl)bis(diphenylmethanol) In toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: m-tolyl aldehyde In toluene at -20℃; for 57h; Inert atmosphere; enantioselective reaction;	95%
Stage #1: m-tolyl aldehyde With (E,4R,5S)-N-allyl-5-cyclohexyl-5-hydroxy-4-morpholinopent-2-enamide In toluene at 20℃; for 0.333333h; Inert atmosphere; Stage #2: diethylzinc In hexane; toluene at 20℃; for 6h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;	95%

diethylzinc (557-20-0) + m-tolyl aldehyde (620-23-5) → (R)-1-(3-tolyl)-1-propanol (32019-31-1, 112777-68-1)

Conditions	Yield
Stage #1: diethylzinc; m-tolyl aldehyde With (1S,2R,3S,5S)-6,6-dimethyl-2-morpholinobicyclo[3.1.1]heptan-3-ol; (1R,2S,3R,5R)-6,6-dimethyl-2-morpholinobicyclo[3.1.1]heptan-3-ol In hexane at -15 - 0℃; for 18h; Inert atmosphere; Stage #2: With water; ammonium chloride In hexane at 0℃; optical yield given as %ee; enantioselective reaction;	100%
With 4-methyl-N-{[(1S,2S)-2-(pyrrolidin-1-yl)cyclohexyl]methyl}benzenesulfonamide In hexane at 0℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	97%
With titanium(IV) isopropylate In dichloromethane at 0℃;	96%

1-amino-2-propene (107-11-9) + m-tolyl aldehyde (620-23-5) → Allyl-[1-m-tolyl-meth-(E)-ylidene]-amine (246509-62-6)

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 20h;	100%
With 3 A molecular sieve In benzene at 65℃;

2-bromo-N,N-diphenylacetamide (6335-34-8) + m-tolyl aldehyde (620-23-5) → C22H19NO2

Conditions	Yield
With potassium hydroxide In acetonitrile at 20℃; for 4h; Darzens condensation;	100%
With potassium hydroxide In dichloromethane at 20℃; Darzens condensation;	76%

methylamine (74-89-5) + m-tolyl aldehyde (620-23-5) → N-[(3-methylphenyl)methylene]methanamine (17972-15-5)

Conditions	Yield
at 20℃; for 12h;	100%
at 20℃; for 1h;
In benzene for 2h; Reflux;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + m-tolyl aldehyde (620-23-5) → C24H30N2 (1217526-70-9)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

m-tolyl aldehyde (620-23-5) + trimethyl orthoformate (149-73-5) → 1,1-dimethoxy-1-(3-methylphenyl)methane (90470-72-7)

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 20℃; for 18h;	100%
With Pd(PhCN)2(OTf)2 at 20℃; for 0.5h; Inert atmosphere;	91%
With toluene-4-sulfonic acid In methanol at 20℃; for 2h; Molecular sieve;

N-prenyl-N-propargyltosylamide (132330-44-0) + m-tolyl aldehyde (620-23-5) → C23H27NO3S (1174503-11-7)

Conditions	Yield
Stage #1: N-prenyl-N-propargyltosylamide With ethylmagnesium bromide In tetrahydrofuran at 50℃; for 1h; Stage #2: m-tolyl aldehyde In tetrahydrofuran at 20℃; for 3h;	100%
Stage #1: N-prenyl-N-propargyltosylamide With ethylmagnesium bromide In tetrahydrofuran at 50℃; for 1h; Stage #2: m-tolyl aldehyde In tetrahydrofuran at 20℃; for 3h;

dimethyl (2-oxo-2-(1H-pyrrol-1-yl)ethyl)phosphonate (1346683-43-9) + m-tolyl aldehyde (620-23-5) → (E)-1-(1H-pyrrol-1-yl)-3-(m-tolyl)prop-2-en-1-one (1608108-44-6)

Conditions	Yield
Stage #1: dimethyl (2-oxo-2-(1H-pyrrol-1-yl)ethyl)phosphonate With N-ethyl-N,N-diisopropylamine; lithium chloride In acetonitrile at 0℃; for 0.333333h; Stage #2: m-tolyl aldehyde In acetonitrile at 20℃; for 15h;	100%

1,3-dimethylbarbituric acid (769-42-6) + diethylamine (109-89-7) + m-tolyl aldehyde (620-23-5) → 5,5'-(3-tolylmethylene)bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) diethylaminium salt (1621511-05-4)

Conditions	Yield
In water at 20℃; Inert atmosphere;	100%
With water; dimedone at 20℃; Green chemistry;	97%

dimedone (126-81-8) + diethylamine (109-89-7) + m-tolyl aldehyde (620-23-5) → Diethylammonium 2-((2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(m-tolyl)methyl)-5,5-dimethyl-3-oxocyclohex-1-enolate

Conditions	Yield
In water at 20℃; Inert atmosphere;	100%

1-ethyl-4-ethynylbenzene (40307-11-7) + m-tolyl aldehyde (620-23-5) → 1-(4′-methylphenyl)isoquinoline (101273-46-5)

Conditions	Yield
With palladium diacetate; sodium carbonate; triphenylphosphine In toluene at 80℃; for 2h; Inert atmosphere;	100%

1-ethyl-4-ethynylbenzene (40307-11-7) + m-tolyl aldehyde (620-23-5) → 3-(4-ethylphenyl)-1-(m-tolyl)prop-2-yn-1-ol

Conditions	Yield
Stage #1: 1-ethyl-4-ethynylbenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: m-tolyl aldehyde In tetrahydrofuran at -78℃; for 3h; Inert atmosphere;	100%

cyclohexylamine (108-91-8) + m-tolyl aldehyde (620-23-5) → (E)-N-cyclohexyl-1-(3-tolyl)methanimine

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 15h; Inert atmosphere;	100%

trimethyl phosphonoacetate (5927-18-4) + m-tolyl aldehyde (620-23-5) → (E)-methyl 3-methylcinnamate (82444-40-4, 118315-74-5, 95416-56-1)

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: m-tolyl aldehyde In tetrahydrofuran; paraffin oil at -78 - 20℃; Inert atmosphere;	100%

m-tolyl aldehyde (620-23-5) → 3-methylbenzyl alcohol (587-03-1)

Conditions	Yield
With alumina; isopropyl alcohol at 180℃; under 11251.1 Torr; for 0.666667h; Microwave irradiation; Sealed tube;	99%
With Candida boidinii formate dehydrogenase; Geobacillus stearothermophilus ε‐deaminating L‐lysine dehydrogenase variant 27; nicotinamide adenine dinucleotide In aq. buffer at 30℃; for 24h; pH=7; Reagent/catalyst; Enzymatic reaction;	99%
With triethylamine; isopropyl alcohol; lithium bromide at 20℃; for 48h; Meerwein-Ponndorf-Verley reaction;	98%

Upstream product

• 620-22-4 3-Methylbenzonitrile 
• 1711-06-4 3-Methylbenzoyl chloride 
• 99-04-7 m-Toluic acid 
• 509-14-8 tetranitromethane 
• 40430-79-3 1-methyl-2,4-cyclohexadiencarbaldehyd 
• 108-38-3 m-xylene 
• 4885-02-3 Dichloromethyl methyl ether 
• 108-88-3 toluene 
• 201230-82-2 carbon monoxide 
• 287-92-3 Cyclopentane 
• 6906-25-8 N-(3-methylbenzylidene)aniline 
• 7664-93-9 sulfuric acid 
• 93-61-8 N-methyl-N-phenylformamide 
• 108-24-7 acetic anhydride 

Downstream Products

• 5825-19-4 (E)-4-(3-methylstyryl)pyridine 
• 29263-66-9 α-(3-methylphenyl)-2-pyridylmethanol 
• 100-80-1 3-methylstyrene 
• 3029-79-6 3-methylcinnamic acid 
• 4601-65-4 bis-(4-dimethylamino-phenyl)-m-tolyl-methane 
• 56946-68-0 bis-(2-phenyl-acetylamino)-m-tolyl-methane 
• 6906-25-8 N-(3-methylbenzylidene)aniline 
• 16619-29-7 3-(3-methylphenyl)-1-phenyl-2-propen-1-one 
• 16619-29-7 phenyl m-methylstyryl ketone 
• 106841-03-6 3-chloro-N-(3-methyl-benzyliden)-aniline 
• 10477-84-6 3-methyl-benzaldehyde-(4-nitro-phenylhydrazone) 
• 72190-20-6 (2-m-tolyl-[1,3]dioxolan-4-yl)-methanol 
• 14064-48-3 (E)-3-methylstilbene 
• 42250-02-2 1-(m-tolyl)but-3-yn-1-ol 

Relevant articles and documents

Silica-embedded tert-butyldimethylsilyltrifluoromethanesulfonate catalysts as new solid acid catalysts

Silica-embedded tert-butyldimethylsilyltrifluoromethanesulfonate catalysts were synthesized by a sol-gel method in acidified CCl4, using hexadecyltrimethyl-ammonium bromide as a surfactant. The catalysts were characterized by nitrogen adsorption-desorption isotherms at 77 K; TG-DTA; 1H, 13C, and 29Si solid state MAS/NMR; XRD; XPS; Raman spectroscopy; and FTIR after adsorption of NH3. The characterization data indicated mesoporous solids in which most of the silyl-triflate derivative keeps its integrity. The catalytic tests performed with the methyl ester of 1-cyclopentenylacetic acid in various solvents showed that the reaction selectively leads to 3-methylbenzaldehyde and is sensitive to the solvent accepting ability.

A novel and active catalyst Ag/ZnO for oxidant-free dehydrogenation of alcohols

Nano Ag/ZnO catalysts were prepared by varying load of Ag on ZnO supports using a new and very simple method. The structure of nano Ag/ZnO has been confirmed by various techniques. The Ag/ZnO with 7.4 × 10-5 mol% of Ag has pore size distribution about 2.74 nm and this nano Ag/ZnO is found to be the best catalyst for oxidation of primary and secondary benzyl alcohols into corresponding aldehydes and ketones in oxidant-free at the atmospheric pressure. The influence of various parameters such as: solvent, base, temperature, time of reaction, etc. has been systematically studied on nano Ag/ZnO catalyst.

Selective Encapsulation and Unusual Stabilization of cis-Isomers by a Spherical Polyaromatic Cavity

To explore new cavity functions, we herein employed cis-trans stereoisomers with a N=N, C=C, or C=N unit as guest indicators for a polyaromatic capsule. Thanks to the rigid, spherical cavity with a diameter of ～1 nm, azobenzene and stilbene derivatives ar

A Magnetically Recyclable Palladium-Catalyzed Formylation of Aryl Iodides with Formic Acid as CO Source: A Practical Access to Aromatic Aldehydes

A magnetically recyclable palladium-catalyzed formylation of aryl iodides under CO gas-free conditions has been developed by using a bidentate phosphine ligand-modified magnetic nanoparticles-anchored- palladium(II) complex [2P-Fe 3O 4@SiO 2-Pd(OAc) 2] as catalyst, yielding a wide variety of aromatic aldehydes in moderate to excellent yields. Here, formic acid was employed as both the CO source and the hydrogen donor with iodine and PPh 3as the activators. This immobilized palladium catalyst can be obtained via a simple preparative procedure and can be facilely recovered simply by using an external magnetic field, and reused at least 9 times without any apparent loss of catalytic activity.

A TEMPO-Functionalized Ordered Mesoporous Polymer as a Highly Active and Reusable Organocatalyst

The properties of high stability, periodic porosity, and tunable nature of ordered mesoporous polymers make these materials ideal catalytic nanoreactors. However, their application in organocatalysis has been rarely explored. We report herein for the first time the incorporation of a versatile organocatalyst, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), into the pores of an FDU-type mesoporous polymer via a pore surface engineering strategy. The resulting FDU-15-TEMPO possesses a highly ordered mesoporous organic framework and enhanced stability, and shows excellent catalytic activity in the selective oxidation of alcohols and aerobic oxidative synthesis of 2-substituted benzoxazoles, benzimidazoles and benzothiazoles. Moreover, the catalyst can be easily recovered and reused for up to 7 consecutive cycles.