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529-20-4

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529-20-4 Usage

Chemical Properties

clear colorless to yellow liquid

Uses

o-Tolylaldehyde, is a simple aromatic aldehyde that has many industrial applications, and can also be used as a building block in different chemical synthesis.

Definition

ChEBI: A tolualdehyde compound with the methyl substituent at the 2-position.

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 7175, 1983 DOI: 10.1021/ja00362a028Tetrahedron Letters, 43, p. 1395, 2002 DOI: 10.1016/S0040-4039(02)00027-8

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Methylbenzaldehyde is incompatible with strong bases and strong reducing agents. 2-Methylbenzaldehyde is also incompatible with strong oxidizers. 2-Methylbenzaldehyde may react with ketones, sulfuric acid, nitric acid, caustics and ammonia. .

Fire Hazard

2-Methylbenzaldehyde is combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 529-20-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 9 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 529-20:
(5*5)+(4*2)+(3*9)+(2*2)+(1*0)=64
64 % 10 = 4
So 529-20-4 is a valid CAS Registry Number.

529-20-4 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (A10172)  o-Tolualdehyde, 98%, stab. with 0.1% hydroquinone   

  • 529-20-4

  • 25g

  • 348.0CNY

  • Detail
  • Alfa Aesar

  • (A10172)  o-Tolualdehyde, 98%, stab. with 0.1% hydroquinone   

  • 529-20-4

  • 100g

  • 967.0CNY

  • Detail
  • Alfa Aesar

  • (A10172)  o-Tolualdehyde, 98%, stab. with 0.1% hydroquinone   

  • 529-20-4

  • 500g

  • 3810.0CNY

  • Detail

529-20-4SDS

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 o-tolualdehyde

1.2 Other means of identification

Product number -
Other names o-Tolualdehyde

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:529-20-4 SDS

529-20-4Synthetic route

2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With iodosylbenzene; Cl-CH2-PS supported 5-amino-1,10-phenanthroline-Ru In acetonitrile at 60℃; for 2h;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 sym-collidinium chlorochromate; periodic acid In acetonitrile at 20℃; for 0.166667h; Time; Solvent;100%
2-methylbenzyl trimethylsilyl ether
80515-66-8

2-methylbenzyl trimethylsilyl ether

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With nitrogen dioxide at 20℃; for 0.0833333h;100%
With allyltriphenylphopsphonium peroxodisulfate In acetonitrile for 0.25h; Heating;98%
With trinitratocerium(IV) bromate for 0.33h; Heating;96%
2-diacetoxymethyltoluene
31675-37-3

2-diacetoxymethyltoluene

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With sulphated zirconia In acetonitrile at 60℃; for 0.45h; Microwave irradiation;100%
With rice husk supported FeCl3 nanoparticles In ethanol at 70℃; for 0.25h;96%
With indium(III) bromide In water for 0.333333h; Heating;94%
salicylaldoxime
14683-79-5

salicylaldoxime

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With water; 2-nitro-4,5-dichloropyridazin-3(2H)-one In methanol at 150℃; under 10336 Torr; for 0.166667h; Microwave irradiation;98%
With potassium permanganate; 1-n-butyl-3-methylimidazolim bromide at 20℃; for 0.683333h; Ionic liquid; chemoselective reaction;95%
With KMnO4/alumina at 50℃; for 0.666667h;90%
1-chloromethyl-2-methylbenzene
552-45-4

1-chloromethyl-2-methylbenzene

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; for 0.05h; Microwave irradiation;97%
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 4-methylmorpholine N-oxide In tetrahydrofuran at 20℃; for 15h; Reflux;75%
2-(2-methylphenyl)-1,3-dithiolane
67810-92-8

2-(2-methylphenyl)-1,3-dithiolane

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With silica gel; ferric nitrate In hexane at 50℃; for 0.166667h;97%
With indium (III) iodide; dihydrogen peroxide In water; toluene at 20℃; for 15h; Inert atmosphere; Sealed tube;86 mg
o-MeC6H4CHNNHC6H5
59473-50-6

o-MeC6H4CHNNHC6H5

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With water; silica gel; bis(trimethylsilyl)chromate In chloroform for 0.3h; Heating;97%
With cetyltrimethylammonium peroxodisulphate In acetonitrile for 0.416667h; Reflux;94%
2-Methylbenzonitrile
529-19-1

2-Methylbenzonitrile

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With iron; acetic acid; nickel dichloride In methanol; water for 0.666667h; Heating;95%
With iron; acetic acid; nickel dichloride In methanol; water for 0.666667h; Product distribution; Heating;95%
With formic acid; platinum(IV) oxide In water at 55 - 60℃; for 3h;90%
2-(2-methylphenyl)-1,3-dioxolane
64380-54-7

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

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With caro's acid; silica gel In acetonitrile at 20℃; for 0.333333h;95%
With hydrogenchloride; acetone at 20℃; for 0.5h;11.5 g
With hydrogenchloride; water In tetrahydrofuran for 2.5h;
(2-methyl-phenyl)-(morpholin-4-yl)methanone
22978-34-3

(2-methyl-phenyl)-(morpholin-4-yl)methanone

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.0333333h; Inert atmosphere;95%
Stage #1: (2-methyl-phenyl)-(morpholin-4-yl)methanone With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethanesulfonic acid ethyl ester In dichloromethane at 20℃; for 2h; Inert atmosphere;
Stage #2: With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; dichloromethane at -78℃; for 4h; Inert atmosphere;
83%
(2-methylphenyl)(1-pyrrolidinyl)methanone
347908-47-8

(2-methylphenyl)(1-pyrrolidinyl)methanone

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
Stage #1: (2-methylphenyl)(1-pyrrolidinyl)methanone With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethanesulfonic acid ethyl ester In dichloromethane at 20℃; for 2h; Inert atmosphere;
Stage #2: With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; dichloromethane at -78℃; for 4h; Inert atmosphere;
95%
2-(2-Methylphenyl)-1,3-dithian
56637-46-8

2-(2-Methylphenyl)-1,3-dithian

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
Stage #1: 2-(2-Methylphenyl)-1,3-dithian With trichloroisocyanuric acid; silica gel at 20℃; for 0.05h;
Stage #2: With water at 20℃;
94%
With quinolinium monofluorochromate(VI) In acetonitrile for 3h; Heating;94%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In neat (no solvent) at 20℃; for 1h; Milling;94%
2-<2-Methyl-benzyloxy>-tetrahydro-pyran
18483-90-4

2-<2-Methyl-benzyloxy>-tetrahydro-pyran

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With allyltriphenylphopsphonium peroxodisulfate In acetonitrile for 0.25h; Heating;94%
With dipotassium peroxodisulfate; molybdenum trioxide In water; acetonitrile for 0.34h; Reflux;90%
C20H29NO

C20H29NO

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
Stage #1: C20H29NO With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethanesulfonic acid ethyl ester In dichloromethane at 20℃; for 2h; Inert atmosphere;
Stage #2: With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; dichloromethane at -78℃; for 4h; Inert atmosphere;
94%
triformylamine
25891-31-0

triformylamine

toluene
108-88-3

toluene

A

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

B

N-[bis(4-methylphenyl)methyl]formamide
127568-35-8

N-[bis(4-methylphenyl)methyl]formamide

C

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With aluminium trichloride at 0℃; for 5h; Condensation; formylation;A n/a
B 93%
C n/a
N,N-dibenzyl-2-methylbenzamide
57409-30-0

N,N-dibenzyl-2-methylbenzamide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
Stage #1: N,N-dibenzyl-2-methylbenzamide With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethanesulfonic acid ethyl ester In dichloromethane at 45℃; for 4h; Inert atmosphere;
Stage #2: With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; dichloromethane at -78℃; for 4h; Inert atmosphere;
93%
ortho-toluoyl chloride
933-88-0

ortho-toluoyl chloride

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In benzene for 0.166667h; Ambient temperature;92%
With tri-n-butyl-tin hydride In 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere;87%
With polymethylhydrosiloxane; trifuran-2-yl-phosphane; tetrabutyl ammonium fluoride; potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water at 20℃; for 1h;83%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
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;92%
With mercury(II) fluoride; oxygen In acetonitrile at 25℃; for 24h; Irradiation;85%
2-(o-tolyl)-1,3-oxathiolane
1211405-11-6

2-(o-tolyl)-1,3-oxathiolane

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With copper(II) nitrate monohydrate at 90℃; for 0.1h;92%
N,N-dibutyl-2-methylbenzamide

N,N-dibutyl-2-methylbenzamide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
Stage #1: N,N-dibutyl-2-methylbenzamide With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethanesulfonic acid ethyl ester In dichloromethane at 20℃; for 4h; Inert atmosphere;
Stage #2: With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; dichloromethane at -78℃; for 4h; Inert atmosphere;
92%
o-xylene
95-47-6

o-xylene

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 2h; Irradiation; Green chemistry;91%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 85℃; for 16h;82%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 85℃; for 16h;82%
carbon monoxide
201230-82-2

carbon monoxide

toluene
108-88-3

toluene

A

bis(p-methylphenyl)-methanone
611-97-2

bis(p-methylphenyl)-methanone

B

4,4'-dimethylbenzhydrol
885-77-8

4,4'-dimethylbenzhydrol

C

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

D

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With hydrogen fluoride; boron trifluoride at 45℃; under 37503.8 - 60006 Torr; for 1h; Further byproducts.;A n/a
B n/a
C 91%
D 5%
2-(2-methylbenzylidene)hydrazine carboxamide
16269-44-6

2-(2-methylbenzylidene)hydrazine carboxamide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With potassium permanganate at 20℃; for 1.66667h; Ionic liquid; chemoselective reaction;91%
formic acid
64-18-6

formic acid

ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; dicyclohexyl-carbodiimide at 100℃; for 2.5h; Sealed tube;91%
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; tricyclohexylphosphine In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;85%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube;72%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 4h; Sealed tube;71%
o-Methylbenzamid
527-85-5

o-Methylbenzamid

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With samarium diiodide; phosphoric acid In tetrahydrofuran for 0.000833333h; Ambient temperature;90%
With lithium-tris(diethylamino)hydridoaluminate In tetrahydrofuran for 12h; Ambient temperature;86%
C14H13NO

C14H13NO

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With hydrogenchloride In water; N,N-dimethyl-formamide at 50℃; for 1h;90%
With hydrogenchloride; water at 50℃; for 1h;90%
ethyl 2-methylbenzoate
87-24-1

ethyl 2-methylbenzoate

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With phenylsilane; cobalt(II) diacetate tetrahydrate; sodium triethylborohydride In 1,2-dimethoxyethane; toluene at 0℃; for 15h; Inert atmosphere; Schlenk technique;89%
With naphthalene In tetrahydrofuran; hexane at 0℃; for 3h;82 % Chromat.
With sodium diisobutyl(t-butoxy)aluminum hydride In tetrahydrofuran; hexane at 0℃; for 6h;83 % Chromat.
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With palladium(II) acetylacetonate; hydrogen; 2,2-dimethylpropanoic anhydride; dicyclohexylphenylphosphine In tetrahydrofuran at 80℃; under 3750.38 Torr; for 20h; Inert atmosphere;88%
With succinic acid anhydride; methylphenylsilane; C58H82O6P2; copper(II) nitrate In tetrahydrofuran at 55℃; for 12h; Schlenk technique; Inert atmosphere;75%
With potassium phosphate; sodium hypophosphite; 2,2-dimethylpropanoic anhydride; palladium diacetate; tricyclohexylphosphine In tetrahydrofuran at 60℃; for 16h;70%
2-methylbenzyl bromide
89-92-9

2-methylbenzyl bromide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
With bis-{4-methoxy-phenyl}-selenoxyde; sodium hydrogencarbonate In acetonitrile at 75℃; for 5h;88%
With potassium hydrogencarbonate; dimethyl sulfoxide for 0.05h; Microwave irradiation;87%
With manganese(IV) oxide In chloroform at 60℃; for 6h;58%
2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

Conditions
ConditionsYield
With zirconium dioxide hydrate; isopropyl alcohol at 60℃; for 0.25h; Meerwein-Ponndorf-Verley Reduction;100%
With 2BH4(1-)*Zn(2+)*Cl2Na2 In acetonitrile at 20℃; for 0.0833333h;98%
With hydrogen In methanol at 20℃; for 5h; chemoselective reaction;98%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

1-(2-methylphenyl)-1-pentanol
73178-44-6

1-(2-methylphenyl)-1-pentanol

Conditions
ConditionsYield
With (S)-1-ethyl-3-morpholinopyrrolidine In tetrahydrofuran at -78℃; for 1h; Addition;100%
In tetrahydrofuran; diethyl ether at -78 - 20℃; for 2h;89%
With C16H18NO(1-)*Li(1+) In tetrahydrofuran at -78℃; for 2h; Solvent; Reagent/catalyst; Inert atmosphere;88%
With carbon monoxide In tetrahydrofuran; diethyl ether at -135℃; for 2h;68%
nitromethane
75-52-5

nitromethane

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

methyl-2 β-nitrostyrene
28638-59-7, 34222-71-4

methyl-2 β-nitrostyrene

Conditions
ConditionsYield
ammonium acetate at 90℃; for 2h;100%
With sodium hydroxide
1,1-dimethylhydrazine
57-14-7

1,1-dimethylhydrazine

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

2-methylbenzaldehyde N,N-dimethylhydrazone
59670-11-0

2-methylbenzaldehyde N,N-dimethylhydrazone

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;100%
With magnesium sulfate In dichloromethane at 20℃; for 16h;66%
acetic anhydride
108-24-7

acetic anhydride

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

2-diacetoxymethyltoluene
31675-37-3

2-diacetoxymethyltoluene

Conditions
ConditionsYield
With sulphated zirconia at 0℃; for 4.2h; regioselective reaction;100%
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 20℃; for 1.2h;98%
With indium(III) bromide at 20℃; for 0.1h;97%
carbon tetrabromide
558-13-4

carbon tetrabromide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

1,1-dibromo-2-(2-methylphenyl)ethene
104464-03-1

1,1-dibromo-2-(2-methylphenyl)ethene

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 1h; Inert atmosphere;
Stage #2: 2-methylphenyl aldehyde In dichloromethane at 0 - 20℃; Inert atmosphere;
100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 2-methylphenyl aldehyde In dichloromethane at 20℃; for 1h; Inert atmosphere;
98%
With triphenylphosphine In dichloromethane at 0℃; for 0.5h;91%
propylamine
107-10-8

propylamine

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

N-(2-methylbenzylidene)propan-1-amine

N-(2-methylbenzylidene)propan-1-amine

Conditions
ConditionsYield
at 20℃; for 12h;100%
With sodium sulfate In dichloromethane for 2h;
at 20℃; for 1h;
at 20℃; for 1h;
triethyl borane
97-94-9

triethyl borane

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

1-(2-methylphenyl)-1-propanol
61017-92-3

1-(2-methylphenyl)-1-propanol

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); tri-tert-butyl phosphine; 1-(Prop-2-enyl)-1,2,3,4,5-pentamethylcyclopenta-2,4-dien In hexane; toluene at 0℃;100%
With tri-tert-butyl phosphine; bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran; hexane; water at 20℃; for 20h;81%
2-bromo-N,N-diphenylacetamide
6335-34-8

2-bromo-N,N-diphenylacetamide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

C22H19NO2

C22H19NO2

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile at 20℃; for 4h; Darzens condensation;100%
With potassium hydroxide In dichloromethane at 20℃; Darzens condensation;75%
2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(2-methylphenyl)-acetonitrile

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(2-methylphenyl)-acetonitrile

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether; chiral salen-based titanium In dichloromethane at -40℃; for 24h;100%
With 2,6-dimethylpyridine; 2C2H5O4S(1-)*C72H104N4O16V2(2+) In dichloromethane at -20℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;97%
With 1H-imidazole; C2H5O4S(1-)*C36H54N2O4V(1+) In dichloromethane at -20℃; for 18h; Inert atmosphere; optical yield given as %ee;96%
With potassium cyanide; 18-crown-6 ether; titanium(salen) complex In dichloromethane at -40℃; for 24h;
2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

methylamine
74-89-5

methylamine

N-[(2-methylphenyl)methylene]methanamine
18100-53-3

N-[(2-methylphenyl)methylene]methanamine

Conditions
ConditionsYield
at 20℃; for 12h;100%
In methanol; dichloromethane for 18h; Molecular sieve;100%
In ethanol at 0 - 40℃;90%
2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

2-methylbenzoic acid (2-methylphenyl)methyl ester
55133-99-8

2-methylbenzoic acid (2-methylphenyl)methyl ester

Conditions
ConditionsYield
With C18BF16(1-)*C34H53F2NiOP2(1+) In toluene at 60℃; for 1h; Glovebox; Inert atmosphere;100%
With phenylmethanethiol; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at 65℃; for 96h; Tishchenko reaction; Inert atmosphere;87%
With Rh(PhBP3)(H)2(NCMe); hydrogen In toluene at 20℃; under 760.051 Torr; for 0.166667h; Tishchenko reaction;81%
With Me2SiCp''2Th(n-C4H9) In benzene-d6 at 25℃; for 24h; Tishchenko reaction; chemoselective reaction;70%
Th(NEtMe)4 In benzene-d6 at 20℃; for 48h; Tishchenko reaction;50 % Chromat.
2-trimethylsilyl-1-phenyl-2-propen-1-one
83845-70-9

2-trimethylsilyl-1-phenyl-2-propen-1-one

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

C20H24O2Si
1094063-87-2

C20H24O2Si

Conditions
ConditionsYield
With tris(2,4,6-trimethoxyphenyl)phosphine In propyl cyanide sila-Morita-Baylis-Hillman reaction; Inert atmosphere;100%
2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

tert-butyl (E)-3-(2'-aminophenyl)propenoate

tert-butyl (E)-3-(2'-aminophenyl)propenoate

tert-butyl (E,E)-3-[2-(2-methylbenzylideneamino)phenyl]propenoate
1147320-04-4

tert-butyl (E,E)-3-[2-(2-methylbenzylideneamino)phenyl]propenoate

Conditions
ConditionsYield
With acetic acid In benzene for 12h; Molecular sieve; Inert atmosphere; optical yield given as %de;100%
benzyl 2-amino-2,2-diphenylacetate
1204177-06-9

benzyl 2-amino-2,2-diphenylacetate

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

benzyl 2-(2-methylbenzylideneamino)-2,2-diphenylacetate
1204177-26-3

benzyl 2-(2-methylbenzylideneamino)-2,2-diphenylacetate

Conditions
ConditionsYield
In benzene Inert atmosphere; Reflux;100%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

Conditions
ConditionsYield
Stage #1: trimethylsilyl cyanide; 2-methylphenyl aldehyde; (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 1h; Product distribution / selectivity; Inert atmosphere;
100%
Conditions
ConditionsYield
at 20℃; for 12h;100%
at 20℃; for 1h;
at 20℃; for 1h;
methyl 3-((tert-butyldimethylsilyl)oxy)-3-(o-tolyl)propanoate

methyl 3-((tert-butyldimethylsilyl)oxy)-3-(o-tolyl)propanoate

Conditions
ConditionsYield
With silver hexafluoroantimonate; 2,6-bis-[1-(2,6-diethylphenylimino)ethyl]pyridine iron(II) chloride In dichloromethane at 20℃; Mukaiyama Aldol Addition; Inert atmosphere;100%
With silver hexafluoroantimonate; [RuCl2((4R)-2-[2-(diphenylphosphino)phenyl]-4-phenyl-4,5-dihydro-1,3-oxazole)2] In dichloromethane at 20℃; Mukaiyama Aldol Addition;92%
With C33H29FeNO2P(1+)*I(1-) In acetonitrile at 20℃; for 0.25h; Mukaiyama aldol reaction;70%
cis, trans-1,3-dimethylaminocyclohexane
2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

C24H30N2
1217526-75-4

C24H30N2

Conditions
ConditionsYield
In methanol at 20℃; Molecular sieve;100%
In methanol at 20℃; Molecular sieve;
propargyl bromide
106-96-7

propargyl bromide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

1-(o-tolyl)but-3-yn-1-ol
1250596-10-1

1-(o-tolyl)but-3-yn-1-ol

Conditions
ConditionsYield
With zinc In tetrahydrofuran at 0℃; for 1h;100%
With magnesium; mercury dichloride In diethyl ether Inert atmosphere;96%
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 7h; Barbier Coupling Reaction; Inert atmosphere; chemoselective reaction;90%
(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

(R)-N-(2-methylbenzylidene)-1-phenylethanamine
858371-56-9

(R)-N-(2-methylbenzylidene)-1-phenylethanamine

Conditions
ConditionsYield
In toluene at 100℃; for 2h; Inert atmosphere;100%
With magnesium sulfate In dichloromethane at 20℃; for 24h;
N-prenyl-N-propargyltosylamide
132330-44-0

N-prenyl-N-propargyltosylamide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

C23H27NO3S
1363388-68-4

C23H27NO3S

Conditions
ConditionsYield
Stage #1: N-prenyl-N-propargyltosylamide With ethylmagnesium bromide In tetrahydrofuran at 50℃; for 1h;
Stage #2: 2-methylphenyl 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: 2-methylphenyl aldehyde In tetrahydrofuran at 20℃; for 3h;
dimethyl (2-oxo-2-(1H-pyrrol-1-yl)ethyl)phosphonate
1346683-43-9

dimethyl (2-oxo-2-(1H-pyrrol-1-yl)ethyl)phosphonate

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

(E)-1-(1H-pyrrol-1-yl)-3-(o-tolyl)prop-2-en-1-one
1608108-45-7

(E)-1-(1H-pyrrol-1-yl)-3-(o-tolyl)prop-2-en-1-one

Conditions
ConditionsYield
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: 2-methylphenyl aldehyde In acetonitrile at 20℃; for 15h;
100%
2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

4-methoxycarbonyl aniline
619-45-4

4-methoxycarbonyl aniline

methyl (E)-4-((2-methylbenzylidene)amino)benzoate

methyl (E)-4-((2-methylbenzylidene)amino)benzoate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 18h; Inert atmosphere; Molecular sieve;100%

529-20-4Relevant articles and documents

Chromium trioxide supported onto wet silica gel: Rapid oxidation of alcohols to carbonyl compounds under microwave irradiation in solventless system

Heravi, Majid M.,Farhangi, Nasrin,Beheshtiha, Yahya Sh.,Assadolah, Karim,Ghassemzadeh, Mitra,Tabar-Hydar, Koroush

, p. 2883 - 2885 (2002)

In an environmentally benign system, alcohols are rapidly oxidized to carbonyl compounds using CrO3 supported onto wet silica gel as an oxidant under microwave irradiation.

Synthesis of Oxetans by Photocycloaddition of Aromatic Aldehydes to Hexamethyl(Dewar benzene)

Carless, Howard A. J.,Trivedi, Harish S.

, p. 950 - 951 (1981)

U.v. irradiation of the aldehydes (3) in the presence of hexamethyl(Dewar benzene) yields the tricyclic oxetans (4) and (5) in competition with hexamethylbenzene formation.

Palladium-Catalyzed ortho C?H Arylation of Benzaldehydes Using ortho-Sulfinyl Aniline as Transient Auxiliary

Mu, Delong,He, Gang,Chen, Gong

, p. 2423 - 2426 (2018)

A PdII-catalyzed ortho-(Csp2)–H arylation reaction of benzaldehydes using a catalytic amount of 2-(methylsulfinyl)aniline as transient auxiliary was developed. This reaction is compatible with a broad range of benzaldehyde and aryl iodide substrates. Compared with other related reaction systems, an excellent regioselectivity for ortho-C(sp2)?H bonds over benzylic C(sp3)?H bonds was obtained for ortho-alkyl-benzaldehyde substrates.

ULTRASOUND IN ORGANIC SYNTHESIS 10. SELECTIVE ORTHO-LITHIATION OF THE BOUVEAULT REACTION INTERMEDIATE

Einhorn, J.,Luche, J. L.

, p. 1793 - 1796 (1986)

The Bouveault reaction intermadiate prepared under sonochemical conditions easily undergoes orthodirected lithiation.The use of tetrahydropyran as a solvent dramatically increases the rates and yields of metallation which can be accomplished with an in situ generated alkyl-lithium.

Oxidation of o-Xylene to Phthalic Anhydride over V2O5/TiO2 Catalysts. I. Influence of Catalyst Composition, Preparation Method and Operating Conditions on Conversion and Product Selectivities

Dias, Cristina R.,Portela, M. Farinha,Bond, Geoffrey C.

, p. 344 - 352 (1995)

The oxidation of o-xylene and of o-tolualdehyde over V2O5/TiO2 (anatase) catalysts has been studied at 533-633 K under steady state conditions; catalysts were prepared either by wet impregnation employing NH4VO3 solution or by a grafting technique with VO(O-i-C4H9)3.At lower temperatures and lower contact times, for both o-xylene and o-tolualdehyde, part of the reactant feed disappeared due to the formation of an involatile polymeric residue, the formation of which was enhanced at lower temperatures, lower contact times, and higher organic reactant concentrations.At lower contact times, the part of the residue deposited on the catalyst surface constituted an important CO2 source.The catalyst prepared by grafting showed higher phthalic anhydride selectivity and less of the residue.The formation of nonselective oxidation products seems to be favoured by uncoated TiO2 since 0.6percent V2O5/TiO2 showed higher CO2 selectivity than other catalysts.Crystalline V2O5 caused greater residue formation.

Confining task-specific ionic liquid in silica-gel matrix by sol-gel technique: A highly efficient catalyst for oxidation of alcohol with molecular oxygen

Liu, Lin,Ma, Juanjuan,Xia, Jiyin,Li, Luodan,Li, Chunlong,Zhang, Xiaobo,Gong, Junyan,Tong, Zhiwei

, p. 323 - 326 (2011)

A novel catalytic system was developed through confinement of TEMPO task-specific ionic liquid (TEMPO-IL) with CuCl2 in a silica-gel matrix by sol-gel technique. The obtained TEMPO-IL/CuCl2/silica-gel catalytic system was effective f

Method for generating benzaldehyde by catalyzing alpha-monosubstituted styrene to be oxidized by N-hydroxyphthalimide

-

Paragraph 0060-0062, (2021/01/24)

The invention discloses a method for generating benzaldehyde by catalyzing alpha-mono-substituted styrene to be oxidized through N-hydroxyphthalimide. According to the method, N-hydroxyphthalimide isused as a catalyst, oxygen is used as an oxidizing agent, and an alpha mono-substituted styrene compound is oxidized in an organic solvent to obtain the benzaldehyde derivative. The method has the advantages of simple reaction operation, low cost, mild conditions, high yield, no heavy metal pollution and the like.

Aryl aldiketone and synthesis method thereof

-

Paragraph 0018, (2021/09/26)

The invention discloses an aryl aldehyde ketone and a synthesis method thereof, wherein an aryl aldehyde is synthesized from cheap olefin as a raw material. A commercially available inexpensive olefin is used as a raw material, ether is used as an additive, molecular oxygen serves as a sole oxidizing agent, water is used as a solvent, and the aldehyde and ketone are synthesized by column chromatography under a photocatalytic condition. The invention has the advantages of mild reaction conditions, green and environmental protection, simple experimental operation, good reaction selectivity, high product yield and the like.

Method for preparing aldehyde compounds by oxidative cleavage of carbon-carbon bonds of terminal alkene compounds

-

Paragraph 0037-0038; 0089-0090, (2021/06/06)

The invention discloses a method for preparing aldehyde compounds by oxidizing and breaking carbon-carbon bonds of terminal alkene compounds. The method comprises the following steps: adding an alkene-terminated compound, an additive and a nitrogen-doped mesoporous carbon-loaded monatomic catalyst into a fatty primary alcohol solvent, putting into a pressure container, sealing, introducing oxygen source gas with a certain pressure, controlling the pressure of the oxygen source gas to be 0.1-1MPa and the reaction temperature to be 80-150 DEG C, and obtaining a reaction product, namely the aldehyde compound. The nitrogen-doped mesoporous carbon-loaded monatomic catalyst adopted by the invention is high in activity, the highest separation yield of the aldehyde compound as a reaction product reaches 99%, the method is wide in application range, the reaction conditions are easy to control, the catalyst can be recycled, the post-treatment is simple, and the method is suitable for industrial production.

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