529-20-4

Basic information

• Product Name: 2-Methylbenzaldehyde
• Synonyms: o-Tolualdehyde, 98%, stab. with 0.1% hydroquinone;O-Tolualdehyde, 98%, stabilized;o-Tolualdehyde,2-Methylbenzaldehyde;2-Formyltoluene, o-Tolualdehyde;o-Tolualdehyde, stabilized, 98% 100GR;o-Tolualdehyde, stabilized, 98% 25GR;2-METHYLBENZALDEHYDE (STABILISED WITH HY;o-Tolualdehyde, Stabilized with 0.1 Percent Hydroquinone
• CAS NO: 529-20-4
• Molecular Formula: C₈H₈O
• Molecular Weight: 120.15
• EINECS: 208-452-2
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Pyridines ,Halogenated Heterocycles
• Mol File: 529-20-4.mol
• Article Data: 549

Chemical Properties

• Melting Point: -35 °C
• Boiling Point: 199-200 °C(lit.)
• Flash Point: 153 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.039 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.315mmHg at 25°C
• Refractive Index: n20/D 1.546(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• Water Solubility: slightly soluble
• Sensitive: Air Sensitive
• Merck: 14,9527
• BRN: 605841
• CAS DataBase Reference: 2-Methylbenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylbenzaldehyde(529-20-4)
• EPA Substance Registry System: 2-Methylbenzaldehyde(529-20-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/38
• Safety Statements: 26-39-37/39
• RIDADR: 1993
• WGK Germany: 3
• F: 2-10
• HazardClass: AIR SENSITIVE
• PackingGroup: Ⅲ
• Hazardous Substances Data: 529-20-4(Hazardous Substances Data)

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

General Description

Clear liquid.

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.

Synthetic route

2-methyl-benzyl alcohol (89-95-2) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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 aldehyde (529-20-4)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4)

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

C20H29NO → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) + toluene (108-88-3) → 4-methyl-benzaldehyde (104-87-0) + N-[bis(4-methylphenyl)methyl]formamide (127568-35-8) + 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) → 2-methylphenyl aldehyde (529-20-4)

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;	92%
With mercury(II) fluoride; oxygen In acetonitrile at 25℃; for 24h; Irradiation;	85%

2-(o-tolyl)-1,3-oxathiolane (1211405-11-6) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
With copper(II) nitrate monohydrate at 90℃; for 0.1h;	92%

N,N-dibutyl-2-methylbenzamide → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) + toluene (108-88-3) → bis(p-methylphenyl)-methanone (611-97-2) + 4,4'-dimethylbenzhydrol (885-77-8) + 4-methyl-benzaldehyde (104-87-0) + 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4)

Conditions	Yield
With potassium permanganate at 20℃; for 1.66667h; Ionic liquid; chemoselective reaction;	91%

formic acid (64-18-6) + ortho-methylphenyl iodide (615-37-2) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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 → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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) → 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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-methyl-benzyl alcohol (89-95-2)

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → 1-(2-methylphenyl)-1-pentanol (73178-44-6)

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → methyl-2 β-nitrostyrene (28638-59-7, 34222-71-4)

Conditions	Yield
ammonium acetate at 90℃; for 2h;	100%
With sodium hydroxide

1,1-dimethylhydrazine (57-14-7) + 2-methylphenyl aldehyde (529-20-4) → 2-methylbenzaldehyde N,N-dimethylhydrazone (59670-11-0)

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → 2-diacetoxymethyltoluene (31675-37-3)

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → 1,1-dibromo-2-(2-methylphenyl)ethene (104464-03-1)

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → N-(2-methylbenzylidene)propan-1-amine

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → 1-(2-methylphenyl)-1-propanol (61017-92-3)

Conditions	Yield
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-methylphenyl aldehyde (529-20-4) → C22H19NO2

Conditions	Yield
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) + ethyl cyanoformate (623-49-4) → (2S)-O-ethoxycarbonyl-2-hydroxy-2-(2-methylphenyl)-acetonitrile

Conditions	Yield
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) + methylamine (74-89-5) → N-[(2-methylphenyl)methylene]methanamine (18100-53-3)

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

Conditions	Yield
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-methylphenyl aldehyde (529-20-4) → C20H24O2Si (1094063-87-2)

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

2-methylphenyl aldehyde (529-20-4) + tert-butyl (E)-3-(2'-aminophenyl)propenoate → tert-butyl (E,E)-3-[2-(2-methylbenzylideneamino)phenyl]propenoate (1147320-04-4)

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → benzyl 2-(2-methylbenzylideneamino)-2,2-diphenylacetate (1204177-26-3)

Conditions	Yield
In benzene Inert atmosphere; Reflux;	100%

trimethylsilyl cyanide (7677-24-9) + 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
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	Yield
at 20℃; for 12h;	100%
at 20℃; for 1h;
at 20℃; for 1h;

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

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → C24H30N2 (1217526-75-4)

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

propargyl bromide (106-96-7) + 2-methylphenyl aldehyde (529-20-4) → 1-(o-tolyl)but-3-yn-1-ol (1250596-10-1)

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → (R)-N-(2-methylbenzylidene)-1-phenylethanamine (858371-56-9)

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → C23H27NO3S (1363388-68-4)

Conditions	Yield
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) + 2-methylphenyl aldehyde (529-20-4) → (E)-1-(1H-pyrrol-1-yl)-3-(o-tolyl)prop-2-en-1-one (1608108-45-7)

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

2-methylphenyl aldehyde (529-20-4) + 4-methoxycarbonyl aniline (619-45-4) → methyl (E)-4-((2-methylbenzylidene)amino)benzoate

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

Upstream product

• 5292-03-5 diethyl [phenyl(phenylamino)methylidene]phosphoramidate 
• 52920-02-2 (1R,2R)-rel-2-(Methoxycarbonyl)cyclopropanecarboxylic acid 
• 52920-01-1 Cyclopropanecarboxylic acid, 2-formyl-, methyl ester, (1R,2S)-rel- (9CI) 
• 5291-99-6 N-[5-(3,5-dichlorobenzyl)-1,3-thiazol-2-yl]-2-(pyrimidin-2-ylsulfanyl)acetamide 
• 5291-98-5 N-cyano-3-nitrobenzamide 
• 5291-97-4 N-cyano-4-nitrobenzamide 
• 5291-95-2 N-cyano-3-(dimethylamino)benzamide 
• 52919-42-3 2-methylenesuccinic acid, ester with propane-1,2-diol (1:2) 
• 529-19-1 o-Tolunitrile 
• 52919-08-1 (5S,7aR)-N,N-diethyl-1,3-dioxo-2-phenylhexahydro-1H-pyrrolo[1,2-c]imidazole-5-carboxamide 
• 5291-90-7 3,4-Dimethylenecyclobut-1-ene 
• 52918-93-1 1,4:3,6-Dianhydro-D-mannitol mono-9-octadecenoate 
• 52918-92-0 CHENODEOXYCHOLIC ACID-24-13C 
• 52918-86-2 1,4-DIBROMOADAMANTANE 

Downstream Products

• 22084-89-5 3-(2-METHYLPHENYL)PROPIONIC ACID 
• 19564-40-0 3-O-TOLYL-PROPIONALDEHYDE 
• 74239-96-6 [2-[4-(dihexylamino)-2-methylbenzylidene]benzo[b]thien-3(2H)-ylidene]malononitrile S,S-dioxide 
• 62882-00-2 8-METHYL-ISOQUINOLINE 

Recommend Products

• 103987-51-5  (E)-2-methyl-3-(o-tolyl)acrylic acid 
• 110-89-4  piperidine 
• 516-05-2  methyl-propanedioic acid 
• 106-57-0  Glycine anhydride 
• 128-09-6  N-chloro-succinimide 
• 89-95-2  2-methyl-benzyl alcohol 
• 123-73-9  trans-Crotonaldehyde 
• 75-17-2  formaldoxime 
• 17333-74-3  2-methylbenzene diazonium 
• 100381-58-6  (3,5-dimethyl-1H-pyrazol-1-yl) (o-tolyl)methanone 
• 2373-76-4  2-methylcinnamic acid 
• 108-24-7  acetic anhydride 
• 53219-32-2  diethyl 2,6-dimethyl-4-(o-tolyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 141-97-9  ethyl acetoacetate