104-87-0

Basic information

• Product Name: p-Tolualdehyde
• Synonyms: p-Toluic aldehyde;p-Tolualdehyde ,98%;4-Formyltoluene, p-Tolualdehyde;p-Tolualdehyde, 97% 100GR;p-Tolualdehyde, 99+% 100GR;4-METHYLPIPERIDINE FOR SYNTHESIS;4-METHYLBENZALDEHYDE FOR SYNTHESIS;p-Tolualdehyde 97%
• CAS NO: 104-87-0
• Molecular Formula: C₈H₈O
• Molecular Weight: 120.15
• EINECS: 203-246-9
• Product Categories: Aldehydes;Building Blocks;C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Aromatic Aldehydes & Derivatives (substituted);API intermediates;Benzaldehyde (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials
• Mol File: 104-87-0.mol
• Article Data: 1436

Chemical Properties

• Melting Point: -6 °C
• Boiling Point: 204-205 °C(lit.)
• Flash Point: 176 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.019 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.263mmHg at 25°C
• Refractive Index: n20/D 1.545(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: water: soluble0.25 g/L at 25°C
• Explosive Limit: 0.9-5.6%(V)
• Water Solubility: 0.25 g/L (25 ºC)
• Sensitive: Air Sensitive
• BRN: 385772
• CAS DataBase Reference: p-Tolualdehyde(CAS DataBase Reference)
• NIST Chemistry Reference: p-Tolualdehyde(104-87-0)
• EPA Substance Registry System: p-Tolualdehyde(104-87-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-36/38
• Safety Statements: 26-36-37/39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 1
• RTECS: CU7034500
• F: 9-23
• TSCA: Yes
• Hazardous Substances Data: 104-87-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to pale yellow liquid

Uses

Different sources of media describe the Uses of 104-87-0 differently. You can refer to the following data:
1. p-Tolualdehyde is made by the Vilsmeier reaction employing toluene and dimethylformamide or the Guttermann–Koch reaction employing toluene and carbon monoxide.
2. p-Tolualdehyde is used as an intermediate for the synthesis of pharmaceuticals, dyes perfumes and agrochemicals. It is also used as a fixative of flavorings. It is also used as an important organic intermediates, used for spices, triphenylmethane dye synthesis, etc.
3. p-Tolualdehyde may be used as an analytical reference standard for the quantification of the analyte in the following:Air samples using high-performance liquid chromatography with UV detection (HPLC-UV).Mango cultivars using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS).

Definition

ChEBI: A tolualdehyde compound with the methyl substituent at the 4-position.

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 7175, 1983 DOI: 10.1021/ja00362a028Tetrahedron Letters, 29, p. 6265, 1988 DOI: 10.1016/S0040-4039(00)82321-7

General Description

p-Tolualdehyde (4-Methylbenzaldehyde) is an aromatic aldehyde. It has been generated as major oxygenated product during the UV light irradiated oxygenation of p-xylene, via photoinduced electron transfer mechanism. It undergoes condensation reaction with diiron μ-ethylidyne complex to afford μ-vinylcarbyne complex (92% yield).

Flammability and Explosibility

Notclassified

Purification Methods

Steam distil the aldehyde, dry it with CaSO4, then fractionally distil it. [Beilstein 7 IV 672.]

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

Synthetic route

4-Methylbenzyl alcohol (589-18-4) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With dinitrogen tetraoxide; ferric nitrate In dichloromethane Ambient temperature; further oxidizing agent, further conditions and solvents;	100%
In ethanol at 40℃; for 9h;	100%
With TGSE; sodium hydrogencarbonate; sodium carbonate In water for 1.66667h; Electrochemical reaction;	100%

para-xylene (106-42-3) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With oxygen; 10-methyl-9-phenylacridin-10-ium perchlorate In chloroform at 24.84℃; for 10h; Oxidation; Pyrolysis; visible light;	100%
With sulfuric acid; 9-mesityl-2,7,10-trimethylacridinium perchlorate; water; oxygen In acetonitrile at 24.84℃; for 1.33333h; Quantum yield; Reagent/catalyst; Irradiation;	100%
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate; acetic acid at 20℃; under 760.051 Torr; chemoselective reaction;	100%

4-methylbenzaldehyde semicarbazone (120445-48-9, 3030-95-3) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With hydrogenchloride; Tonsil In ethyl acetate for 2h; Heating;	100%
With copper(II) sulfate In tetrahydrofuran; methanol; water for 48h; Heating;	95%
With potassium permanganate; montmorillonite K-10 for 0.25h;	94%

p-tolylmethylenediacetate (2929-93-3) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With [NO(1+)*18-crown-6*H(NO3)2(1-)]; silica gel In dichloromethane at 20℃; for 0.0833333h;	100%
With sulphated zirconia In acetonitrile at 60℃; for 0.3h; Microwave irradiation;	100%
With Montmorillonite K10 In dichloromethane for 0.333333h; Heating;	99%

p-tolualdehyde p-toluenesulfonylhydrazone (40739-81-9) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 48h; Heating;	100%
With Cr-MCM-41 zeolite on silica gel for 0.15h; microwave irradiation;	98%
Amberlyst 15 In water; acetone at 80℃; for 24h;	86%
With polymer-supported phenyliodine(III) diacetate; water In dichloromethane at 20℃; for 2h; Oxidation;	78%

4-methylbenzaldehyde phenylhydrazone (2829-25-6) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 6.5h; Heating;	100%
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.133333h; Heating;	95%
With CuCl*Kieselghur; oxygen In dichloromethane at 20℃; for 0.5h;	94%

N,N-diethyl-4-methylselenobenzamide (160594-72-9) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 3h;	100%

trimethyl(4-methylbenzyloxy)silane (89200-92-0) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With nitrogen dioxide at 20℃; for 0.0833333h;	100%
With phosphomolybdic acid In toluene for 0.166667h; Heating;	97%
With allyltriphenylphopsphonium peroxodisulfate In acetonitrile for 0.25h; Heating;	96%

1-ethenyl-4-methylbenzene (622-97-9) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With sodium periodate; C31H29Br2N3Ru*CH2Cl2 In water; ethyl acetate; acetonitrile at 25℃; for 0.5h; Inert atmosphere; Schlenk technique;	100%
With tert.-butylhydroperoxide; manganese(II,III) oxide In acetonitrile at 70℃; for 3h;	98%
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; Reagent/catalyst; Solvent; Green chemistry; chemoselective reaction;	96%

N-(2-hydroxyl-1-(2-pyridyl)-2-(4-methylphenyl)ethyl)benzenecarbothioamide (1203650-44-5) → bis(3-phenyl-1-imidazo[1,5-a]pyridyl)-4-methylphenylmethane (1203650-52-5) + 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With pyridine; iodine In tetrahydrofuran at 20℃; for 0.5h;	A 100% B n/a

6-hydroxy-4-methylcyclohex-1-enecarbaldehyde → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether In chloroform at 20℃; for 24h; regioselective reaction;	100%

carbon monoxide (201230-82-2) + toluene (108-88-3) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With trifluorormethanesulfonic acid at 24.85℃; under 56886.3 Torr; for 0.5h; Product distribution; Further Variations:; Pressures; Temperatures;	99.1%
With 1,10-Phenanthroline; triphenylphosphine; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; scandium tris(trifluoromethanesulfonate); 1-n-butyl-3-methylimidazolium hexafluoroantimonate; cerium triflate at 50℃; under 15001.5 Torr; for 5h; Reagent/catalyst; Autoclave; Inert atmosphere;	76.8%
With trifluorormethanesulfonic acid under 95000.1 Torr; for 4h; Ambient temperature;	72 % Chromat.

4-methylbenzoic acid ethyl ester (94-08-6) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
Stage #1: 4-methylbenzoic acid ethyl ester With morpholine; diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 3.16667h; Inert atmosphere; Stage #2: With diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere;	99%
With sodium tris(diethylamino)aluminum hydride In tetrahydrofuran; dodecane at 0℃; for 24h;	93%
With phenylsilane; cobalt(II) diacetate tetrahydrate; sodium triethylborohydride In 1,2-dimethoxyethane; toluene at 25℃; for 15h; Inert atmosphere; Schlenk technique;	92%

1,2-di-p-tolyl-ethanone (51490-06-3) + aniline (62-53-3) → 4-methyl-N-phenylbenzamide (6833-18-7) + 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With 1,10-Phenanthroline; copper(II) chloride dihydrate; oxygen In acetonitrile under 760.051 Torr; for 24h; Reflux;	A 99% B n/a

para-xylene (106-42-3) → terephthalic acid (100-21-0) + 4-methyl-benzaldehyde (104-87-0) + 4-Carboxybenzaldehyde (619-66-9) + p-Toluic acid (99-94-5)

Conditions	Yield
With hydrogen bromide; oxygen; acetic acid; cobalt(II) acetate; manganese(II) acetate In water at 190℃; under 16501.7 Torr; for 1h; Product distribution / selectivity;	A 98.1% B 0.2% C 0.4% D 0.4%
With oxygen; acetic acid; palladium diacetate; antimony(III) acetate In water at 182 - 195℃; under 16501.7 - 20929.4 Torr; for 1 - 1.5h; Product distribution / selectivity;	A 50.3% B 7.2% C 6.4% D 6.2%
With hydrogen bromide; oxygen; acetic acid; zirconium oxyacetate; cobalt(II) acetate In water at 190℃; under 16501.7 Torr; for 1h; Product distribution / selectivity;	A 4.9% B 3% C 1.9% D 36.9%

4-Methylbenzyl chloride (104-82-5) → 4-methyl-benzaldehyde (104-87-0)

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;	94%
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 1.5h;	93%

p-methylbenzaldehyde oxime (3235-02-7, 3717-15-5, 3717-16-6, 140461-26-3, 140461-27-4) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With CuCl*Kieselghur; oxygen In dichloromethane at 20℃; for 0.333333h;	98%
Stage #1: p-methylbenzaldehyde oxime With hexachlorodisilane; silica gel In toluene at 110℃; for 0.5h; Stage #2: With water In toluene for 0.5h;	97%
In dichloromethane at 20℃; for 4h;	96%

2-((4-methylbenzyl)oxy)tetrahydro-2H-pyran (18484-04-3) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With zeofen (zeolite HZSM-5, Fe(NO3)3*9H2O) In dichloromethane for 6h; Heating;	98%
With chromium(VI) oxide; HZSM-5 zeolite for 0.0333333h; microwave irradiation;	95%
With NTPPPODS In acetonitrile for 0.166667h; Reflux;	94%

C16H18OSe (79439-44-4) → 4-methylbenzyl nitrate (13527-05-4) + p-methylbenzeneseleninic acid (66361-14-6) + 4-methyl-benzaldehyde (104-87-0) + C16H18OSe*HNO3 + seleninous acid

Conditions	Yield
With nitric acid In dichloromethane at -5 - 0℃; for 1h;	A 98% B n/a C n/a D n/a E n/a
With nitric acid In dichloromethane at -5 - 0℃; for 1h;	A n/a B 98% C n/a D n/a E n/a

4-methylethylbenzene (622-96-8) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-methyl-N-[3-(4-diacetoxyiodo)phenoxy-1-propyl]pyrrolidinium 4-methylbenzenesulfonate In dichloromethane at 20℃; for 1.5h; Inert atmosphere;	98%

Sodium; 6-{[1-p-tolyl-meth-(E)-ylidene]-amino}-hexanoate → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;	97.1%

para-methylbenzonitrile (104-85-8) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With lithium diisobutylmorpholinoaluminum hydride In tetrahydrofuran; hexane at 0℃; for 0.5h;	97%
With calcium bis(hypophosphite); calcium acetate; nickel(II) acetate tetrahydrate In ethanol; water at 100℃; for 7h; Sealed tube;	94%
With C13H26B(1-)*K(1+) In tetrahydrofuran for 24h; Ambient temperature;	83%

4-Methylbenzyl bromide (104-81-4) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With water; sodium hydroxide at 20℃; for 0.0666667h; Microwave irradiation;	97%
With dihydrogen peroxide In ethanol for 4h; Reflux; Green chemistry;	95%
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 1.5h;	93%

1-((phenylthio)(p-tolyl)methylthio)benzene (71778-40-0) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With sodium perborate In acetic acid at 25℃; for 2h;	97%
With oxygen; 2,4,6-tris(p-chlorophenyl)pyrylium perchlorate In dichloromethane for 0.2h; Irradiation;	83%

4-methylcinnamic acid (1866-39-3) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With potassium permanganate; Amberlite IR-120; water In dichloromethane at 20℃; for 0.333333h;	97%
With sulfuric acid; quinolinium dichromate(VI) In acetic acid at 29.9℃; Rate constant; Thermodynamic data; ΔHact, ΔSact, ΔGact; var. concentration of reagents;
Multi-step reaction with 2 steps 1: magnesium chloride; ATP / 20 h / pH 7.5 / Enzymatic reaction 2: water / 14 h / 30 °C / Enzymatic reaction View Scheme

N-methoxy-N,4-dimethylbenzamide (122334-36-5) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With lithium diisobutyl-tert-butoxyaluminum hydride In tetrahydrofuran; hexane at 0℃; Reagent/catalyst; Inert atmosphere; chemoselective reaction;	97%
With benzoic acid ethyl ester; copper diisobutyl-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; chemoselective reaction;	96 %Chromat.

4-methylbenzylthiol (4498-99-1) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With dipotassium peroxodisulfate; tetrakis(pyridine)silver(II) peroxodisulfate; oxygen In N,N-dimethyl-formamide at 23℃; under 760.051 Torr; Irradiation;	97%

2-(4-methylphenyl)-1,3-dioxolane (2403-51-2) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With polyaniline-sulfate salt; water for 0.5h; Heating;	96%
With silica-OSO3H; silica gel In toluene at 60 - 70℃; for 1h;	94%
In(OSO2CF3)3 In acetone at 20℃; for 4h;	92%

2-(4-methylphenyl)-1,3-dithiolane (23229-29-0) → 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With tetrachlorosilane; dimethyl sulfoxide In dichloromethane at 20℃; for 0.583333h;	96%
With silica gel In neat (no solvent) at 20℃; for 0.05h;	96%
With sodium nitrate; sulfuric acid; silica gel; 4-nitrobenzylidene diacetate In dichloromethane at 20℃; for 0.25h;	93%

para-xylene (106-42-3) → 4-methylbenzyl nitrate (13527-05-4) + 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile at 40℃; for 0.5h; Irradiation;	A 96% B n/a
With ammonium cerium(IV) nitrate In acetonitrile at 40℃; for 0.5h; Mechanism; Irradiation;	A 96% B n/a
ammonium cerium(IV) nitrate; sodium dodecyl-sulfate In water at 25℃; for 3h;	A 3.95 mmol B 3.10 mmol
With ammonium cerium(IV) nitrate; sodium dodecyl-sulfate In water at 25℃; for 3h; Title compound not separated from byproducts;	A 3.95 mmol B 3.10 mmol
With sodium dodecyl-sulfate; ammonium cerium(IV) nitrate In water at 25℃; for 3h; Product distribution; other reagents, solvents, reac. time;	A 3.95 mmol B 3.1 mmol

Nitroethane (79-24-3) + 4-methyl-benzaldehyde (104-87-0) → 1-(p-tolyl)-2-nitropropene (52287-56-6, 29816-55-5)

Conditions	Yield
With ammonium acetate at 110℃; for 16h;	100%
With (2-hydroxyethyl)ammonium formate at 20℃; for 4.1h; Knoevenagel condensation; Ionic liquid;	95%
With ammonium acetate at 120℃; for 2h;	95%

nitromethane (75-52-5) + 4-methyl-benzaldehyde (104-87-0) → 4-methyl-β-nitrostyrene (7559-36-6)

Conditions	Yield
With C62H54N2O2; copper diacetate In ethanol at 10℃; for 48h; Henry Nitro Aldol Condensation; enantioselective reaction;	100%
With C62H48CuN2O2; copper diacetate; benzaldehyde In ethanol at 10℃; for 48h; Reagent/catalyst; Henry Nitro Aldol Condensation;	100%
With (2-hydroxyethyl)ammonium formate at 20℃; for 0.8h; Knoevenagel condensation; Ionic liquid;	95%

4-methyl-benzaldehyde (104-87-0) + ethane-1,2-dithiol (540-63-6) → 2-(4-methylphenyl)-1,3-dithiolane (23229-29-0)

Conditions	Yield
With silica gel; toluene-4-sulfonic acid In dichloromethane for 1.5h; Heating;	100%
With Cu(OTf)2-SiO2 for 0.5h; Ambient temperature;	99%
With PPA; silica gel In 1,2-dichloro-ethane at 20℃; for 0.5h;	99%

4-methyl-benzaldehyde (104-87-0) + phenylhydrazine (100-63-0) → 4-methylbenzaldehyde phenylhydrazone (2829-25-6)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane	100%
In neat (no solvent) at 20℃; for 0.00277778h;	97%
With oxidized single-walled carbon nanotubes(SWCNs-COOH) In ethanol at 80℃; for 1.25h;	96%

4-methyl-benzaldehyde (104-87-0) + methylamine (74-89-5) → p-methylbenzylidene-methylamine (17972-13-3, 29086-13-3, 53699-34-6)

Conditions	Yield
at 20℃; for 12h;	100%
In methanol; dichloromethane for 18h; Molecular sieve;	86%

4-methyl-benzaldehyde (104-87-0) + benzylamine (100-46-9) → N-benzyl-p-tolylmethanimine (24431-15-0)

Conditions	Yield
In chloroform at 20℃; for 1h;	100%
for 6h; Kinetics; Molecular sieve; Reflux;	100%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;	65%

4-methyl-benzaldehyde (104-87-0) → 4-Methylbenzyl alcohol (589-18-4)

Conditions	Yield
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.133333h;	100%
With sodium tetrahydroborate In methanol at 20℃; for 1h;	100%
With hydrogen at 30℃; under 22502.3 Torr; for 10h; Temperature; Autoclave; Sealed tube; Ionic liquid; chemoselective reaction;	100%

4-methyl-benzaldehyde (104-87-0) → 1,2-di-p-tolylethane-1,2-diol (5173-28-4, 5173-29-5, 24133-59-3, 66749-58-4, 66768-19-2)

Conditions	Yield
With aluminium; potassium hydroxide In methanol at 0℃; for 1h; Inert atmosphere;	100%
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; acetic acid In dichloromethane at 25℃; for 16h; Michael Addition; Inert atmosphere; Irradiation;	99%
With naphthalene; lithium; manganese(ll) chloride In tetrahydrofuran at 22 - 26℃; for 1h; sonication;	98%

4-methyl-benzaldehyde (104-87-0) → p-Toluic acid (99-94-5)

Conditions	Yield
With phosphate-buffered silica gel supported KMnO4 In cyclohexane at 65℃;	100%
With periodic acid; tripropylammonium fluorochromate (VI) In acetonitrile at 0℃; for 1.5h;	100%
With [Cu2C6H4(CHNCH2CH2N(CH2C5H4N)2)2](2+)*2ClO4(1-)=C36H38Cu2N8(ClO4)2; oxygen In acetone at -90.16℃;	100%

4-methyl-benzaldehyde (104-87-0) + allyl bromide (106-95-6) → 1-p-tolyl-3-buten-1-ol (24165-63-7)

Conditions	Yield
With hydrogenchloride; antimony In water for 16h;	100%
With titanium(III) chloride; tin(ll) chloride In water at 20℃; for 8h; Barbier reaction;	100%
With tin(ll) chloride In water at 20℃; for 24h;	99%

4-methyl-benzaldehyde (104-87-0) + ethyl 2-cyanoacetate (105-56-6) → ethyl (E)-2-cyano-3-p-tolylacrylate (2017-88-1)

Conditions	Yield
With L-proline for 0.0833333h; Knoevenagel condensation; microwave irradiation;	100%
With 1,4-diaza-bicyclo[2.2.2]octane In neat liquid at 20℃; for 0.0166667h; Knoevenagel Condensation; Green chemistry;	100%
With ASCPEI In ethanol at 43℃; for 3h; Knoevenagel condensation;	99%

4-methyl-benzaldehyde (104-87-0) + malononitrile (109-77-3) → 2-(4-methylbenzylidene)malononitrile (2826-25-7)

Conditions	Yield
With L-arginine at 20℃; for 0.0833333h; Knoevenagel condensation; Ionic liquid;	100%
With 1,4-diaza-bicyclo[2.2.2]octane In water at 20℃; for 0.0333333h; Knoevenagel Condensation; Green chemistry;	100%
With 2C9H3O6(3-)*2C27H18N6*3Ni(2+)*15H2O*5C2H6O In dichloromethane at 60℃; for 2h; Knoevenagel Condensation; Inert atmosphere;	100%

2,3-dihydro-4H-[1]benzothiopyran-4-one (3528-17-4) + 4-methyl-benzaldehyde (104-87-0) → (Z)-3-(4-methylbenzylidene)thiochroman-4-one (69964-53-0, 135521-92-5, 101001-08-5)

Conditions	Yield
With hydrogenchloride In methanol for 3h;	100%
With sulfuric acid In acetic acid at 20℃; for 0.333333h;	89%
With hydrogenchloride In ethanol for 0.0833333h; Ambient temperature;	64.1%
With piperidine In chloroform for 5h; Reflux;
With sodium hydroxide In ethanol; water at 0℃; for 0.5h;

diethyl (morpholinomethyl)phosphonate (27353-29-3) + 4-methyl-benzaldehyde (104-87-0) → (2-Hydroxy-1-morpholin-4-yl-2-p-tolyl-ethyl)-phosphonic acid diethyl ester

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃; for 1.25h;	100%

1.3-propanedithiol (109-80-8) + 4-methyl-benzaldehyde (104-87-0) → 2-(4-methylphenyl)-1,3-dithiane (56637-44-6)

Conditions	Yield
With lithium tetrafluoroborate at 25℃; for 1h;	100%
With amberlyst-15 In acetonitrile for 1h;	99.97%
With nickel dichloride In dichloromethane	99%

3-methyl-butan-2-one (563-80-4) + 4-methyl-benzaldehyde (104-87-0) → 4-methyl-1-p-tolyl-pent-1-en-3-one (67962-11-2)

Conditions	Yield
barium dihydroxide In ethanol for 1h; Heating;	100%
With sodium hydroxide In water Heating;

N-methylpropargylamine (35161-71-8) + 4-methyl-benzaldehyde (104-87-0) → N-methyl-N-(4-methylbenzyl)prop-2-yn-1-amine (709-86-4)

Conditions	Yield
Stage #1: 4-methyl-benzaldehyde With acetic acid In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: methyl(propargyl)amine In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #3: With sodium tris(acetoxy)borohydride In dichloromethane at 0℃; Inert atmosphere;	100%
With hydrogenchloride; sodium cyanoborohydride 1.) methanol, 15 min, 2.) MeOH, 24 h; Multistep reaction;

propylamine (107-10-8) + 4-methyl-benzaldehyde (104-87-0) → N-((4-methylphenyl)methylene)-1-propanamine (99484-07-8)

Conditions	Yield
at 20℃; for 12h;	100%
With 1-hydrosilatrane In neat (no solvent) at 70℃; for 23h; Sealed tube; Green chemistry;	99%
In methanol at 25℃; Mechanism; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.);

carbon tetrabromide (558-13-4) + 4-methyl-benzaldehyde (104-87-0) → 1-(2,2-dibromovinyl)-4-methylbenzene (60512-56-3)

Conditions	Yield
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-methyl-benzaldehyde In dichloromethane at 0℃; for 2h; Inert atmosphere;	100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-methyl-benzaldehyde In dichloromethane at 0℃; for 2h; Inert atmosphere;	100%
With triphenylphosphine In dichloromethane at 0℃; for 0.5h;	98%

trimethylsilyl cyanide (7677-24-9) + 4-methyl-benzaldehyde (104-87-0) → 2-(4-methylphenyl)-2-(trimethylsilyloxy)acetonitrile (66985-49-7)

Conditions	Yield
With Na(1+)*C7H3NO4(2-)*Cu(2+)*C7H4NO4(1-) at 20℃; for 3h;	100%
Stage #1: 4-methyl-benzaldehyde With scandium tris(trifluoromethanesulfonate); 1-n-butyl-3-methylimidazolium hexafluoroantimonate at 20℃; for 0.166667h; Stage #2: trimethylsilyl cyanide at 20℃; for 0.0833333h; Inert atmosphere;	99%
With C7H3O8S2(3-)*5H2O*Pr(3+) In neat (no solvent) at 40℃; for 0.5h; Inert atmosphere;	99%

diethyl cyanophosphonate (2942-58-7) + 4-methyl-benzaldehyde (104-87-0) → Phosphoric acid cyano-p-tolyl-methyl ester diethyl ester (123346-48-5)

Conditions	Yield
With lithium cyanide In tetrahydrofuran Ambient temperature;	100%

4-acetyltropolone (1738-16-5) + 4-methyl-benzaldehyde (104-87-0) → 4-(4-methylcinnamoyl)tropolone

Conditions	Yield
With potassium hydroxide In methanol at 0℃;	100%

diethylzinc (557-20-0) + 4-methyl-benzaldehyde (104-87-0) → (S)-1-(4-methylphenyl)propan-1-ol (25574-04-3, 112777-65-8, 138809-38-8, 73854-03-2)

Conditions	Yield
(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: 4-methyl-benzaldehyde In toluene at 0 - 20℃; for 48h; Reagent/catalyst; enantioselective reaction;	99%
Stage #1: diethylzinc; 4-methyl-benzaldehyde With diphenyl-((S)-1-((S)-1-phenylethyl)aziridin-2-yl)-methanol In hexane; toluene at 0 - 25℃; for 48.5h; Inert atmosphere; Stage #2: With ammonium chloride In hexane; water; toluene Saturated solution; optical yield given as %ee; enantioselective reaction;	98%

trimethyl(allyl)stannane (762-73-2) + 4-methyl-benzaldehyde (104-87-0) → C14H22OSn

Conditions	Yield
In diethyl ether under 7500600 Torr; for 168h; Product distribution; Ambient temperature;	100%

4-methyl-benzaldehyde (104-87-0) + 2-Pentanone (107-87-9) → (E)-1-(4-tolyl)hex-1-en-3-one (100765-39-7)

Conditions	Yield
barium dihydroxide In ethanol for 1h; Heating;	100%

Upstream product

• 106-42-3 1,4-Dimethylbenzene 

Downstream Products

• 1505-50-6 3-(4-METHYLPHENYL)PROPIONIC ACID 
• 82571-53-7 Ozagrel 
• 54004-38-5 7-methylisoquinoline 
• 158654-75-2 Isoquinoline, 7-(bromomethyl)- (9CI) 
• 42398-73-2 6-Methylisoquinoline 
• 752183-00-9 Isoquinoline, 6-(bromomethyl)- (9CI) 

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