5779-72-6

Basic information

• Product Name: 2,4,5-TRIMETHYLBENZALDEHYDE
• Synonyms: 2,4,5-TRIMETHYLBENZALDEHYDE;Trimethylbenzaldehyde;duryl aldehyde;2,4,5-TRIMETHYLBENZALDEHYDE 97+%;Duraldehyde;2,4,5-Trimethylbenzaldehyde 90%
• CAS NO: 5779-72-6
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.2
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C10 to C21;Carbonyl Compounds
• Mol File: 5779-72-6.mol
• Article Data: 34

Chemical Properties

• Melting Point: 41-46 °C(lit.)
• Boiling Point: 243°C
• Flash Point: 230 °F
• Appearance: /
• Density: 0.988 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• Merck: 14,9839
• CAS DataBase Reference: 2,4,5-TRIMETHYLBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-TRIMETHYLBENZALDEHYDE(5779-72-6)
• EPA Substance Registry System: 2,4,5-TRIMETHYLBENZALDEHYDE(5779-72-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 5779-72-6(Hazardous Substances Data)

Usage

General Description

Dipole moments of 2,4,5-trimethylbenzaldehyde (TMB) isolated in a durene host crystal have been reported to be 1.65 ± 0.09D (difference between the ground state and the lowest singlet) and 1.05 ± 0.06D (difference between the ground state and triplet excited states). TMB has been identified as one of the major volatile constituent present in the leave extracts of Eryngium foetidum L. Based on the phosphorescence excitation and Stark spectral data, it has been observed that a change in temperature and electric field causes a change in the dipole moment of the compound.

Synthetic route

carbon monoxide (201230-82-2) + 1,2,4-Trimethylbenzene (95-63-6) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 3-Formyl-2,5,6-trimethylbenzenesulfonyl fluoride

Conditions	Yield
With antimony pentafluoride; fluorosulphonic acid at 0℃; for 1h;	A 90% B 1%
With antimony pentafluoride; fluorosulphonic acid at 0℃; for 1h; Yields of byproduct given. Title compound not separated from byproducts;	A 90 % Chromat. B n/a

1-bromo-2,4,5-trimethylbenzene (5469-19-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
Stage #1: 1-bromo-2,4,5-trimethylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 6h; Inert atmosphere;	85%
Stage #1: 1-bromo-2,4,5-trimethylbenzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 6h;	85%
With lithium

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With pyridinium chlorochromate In acetonitrile for 4h; Heating;	76%
With 9-mesityl-2,7,10-trimethylacridinium perchlorate; oxygen In acetonitrile at 24.84℃; for 1.33333h; Quantum yield; Reagent/catalyst; Irradiation;	37%
With 9-(benzoyl(cyclohexyl)carbamoyl)-10-phenylacridinium perchlorate In water; acetonitrile at 20℃; for 18h; Irradiation; Green chemistry; chemoselective reaction;	19%

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,4,5-trimethyl-benzyl alcohol (4393-05-9)

Conditions	Yield
With sulfuric acid; water; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile for 1.33333h; Quantum yield; Reagent/catalyst; Irradiation;	A 75% B 15%
With naphthalene-1,4-dicarbonitrile; oxygen In acetonitrile Quantum yield; Irradiation;
With oxygen; 2,6,9,10-tetracyanoanthracene In acetonitrile at 22℃; Product distribution; Mechanism; Quantum yield; Irradiation; photooxidation, other sensitizers, solvents and products;
With oxygen for 24h; Ambient temperature; Irradiation; Yield given. Yields of byproduct given;

1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide (33070-58-5) + 1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,4,5-trimethyl-benzyl alcohol (4393-05-9)

Conditions	Yield
at 135℃; for 2h;	A 22% B 70%

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 1,1',2,3',4,4',5-(heptamethyldiphenyl)methane (23946-68-1) + 2,4,5-trimethyl-benzyl alcohol (4393-05-9) + (2,4,5-trimethylphenyl)nitromethane (60368-03-8) + 2,4,5-Trimethylbenzyl nitrate (60367-99-9)

Conditions	Yield
With Nitrogen dioxide In dichloromethane at 20℃; for 4h; Product distribution; Irradiation; without irradiation;	A 7% B 0.7% C 0.5% D 19.9% E 69.5%

carbon monoxide (201230-82-2) + 1,2,4-Trimethylbenzene (95-63-6) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 3-Formyl-2,5,6-trimethylbenzenesulfonyl fluoride

Conditions	Yield
With antimony pentafluoride; fluorosulphonic acid at 0℃; for 1h;	A 90% B 1%
With antimony pentafluoride; fluorosulphonic acid at 0℃; for 1h; Yields of byproduct given. Title compound not separated from byproducts;	A 90 % Chromat. B n/a

1-bromo-2,4,5-trimethylbenzene (5469-19-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
Stage #1: 1-bromo-2,4,5-trimethylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 6h; Inert atmosphere;	85%
Stage #1: 1-bromo-2,4,5-trimethylbenzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 6h;	85%
With lithium

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With pyridinium chlorochromate In acetonitrile for 4h; Heating;	76%
With 9-mesityl-2,7,10-trimethylacridinium perchlorate; oxygen In acetonitrile at 24.84℃; for 1.33333h; Quantum yield; Reagent/catalyst; Irradiation;	37%
With 9-(benzoyl(cyclohexyl)carbamoyl)-10-phenylacridinium perchlorate In water; acetonitrile at 20℃; for 18h; Irradiation; Green chemistry; chemoselective reaction;	19%

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,4,5-trimethyl-benzyl alcohol (4393-05-9)

Conditions	Yield
With sulfuric acid; water; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile for 1.33333h; Quantum yield; Reagent/catalyst; Irradiation;	A 75% B 15%
With naphthalene-1,4-dicarbonitrile; oxygen In acetonitrile Quantum yield; Irradiation;
With oxygen; 2,6,9,10-tetracyanoanthracene In acetonitrile at 22℃; Product distribution; Mechanism; Quantum yield; Irradiation; photooxidation, other sensitizers, solvents and products;
With oxygen for 24h; Ambient temperature; Irradiation; Yield given. Yields of byproduct given;

1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide (33070-58-5) + 1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,4,5-trimethyl-benzyl alcohol (4393-05-9)

Conditions	Yield
at 135℃; for 2h;	A 22% B 70%

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 1,1',2,3',4,4',5-(heptamethyldiphenyl)methane (23946-68-1) + 2,4,5-trimethyl-benzyl alcohol (4393-05-9) + (2,4,5-trimethylphenyl)nitromethane (60368-03-8) + 2,4,5-Trimethylbenzyl nitrate (60367-99-9)

Conditions	Yield
With Nitrogen dioxide In dichloromethane at 20℃; for 4h; Product distribution; Irradiation; without irradiation;	A 7% B 0.7% C 0.5% D 19.9% E 69.5%

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,4,5-trimethyl-benzyl alcohol (4393-05-9) + (2,4,5-trimethylphenyl)nitromethane (60368-03-8) + 2,4,5-Trimethylbenzyl nitrate (60367-99-9)

Conditions	Yield
With Nitrogen dioxide In dichloromethane at 20℃; for 0.5h; in the dark; Further byproducts given. Title compound not separated from byproducts;	A 4.9% B 2.6% C 21.8% D 67.6%
With Nitrogen dioxide In dichloromethane at 20℃; for 1h; in the dark; Further byproducts given. Title compound not separated from byproducts;	A 4.3% B 2.5% C 23% D 67%
With Nitrogen dioxide In dichloromethane at 20℃; for 4h; in the dark; Further byproducts given. Title compound not separated from byproducts;	A 5.6% B 1.2% C 22.7% D 67.6%
With Nitrogen dioxide In dichloromethane at 20℃; for 2h; in the dark; Further byproducts given. Title compound not separated from byproducts;	A 7.5% B 1.7% C 21.6% D 66.1%

1,2,4,5-tetramethylbenzene (95-93-2) → acetic acid 2,4,5-trimethyl-benzyl ester (18543-92-5) + 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With air; copper diacetate; cobalt(II) acetate; acetic acid; sodium bromide at 150℃; under 15200 Torr; for 1h;	A 63% B 10%

1,2,4,5-tetramethylbenzene (95-93-2) + acetic acid (64-19-7) → acetic acid 2,4,5-trimethyl-benzyl ester (18543-92-5) + 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With air; copper diacetate; cobalt(II) acetate; sodium bromide at 150℃; under 15200 Torr; for 1h;	A 63% B 10%
With sodium nitrate; H5PV2Mo10O40 at 80℃; for 14h;

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,3,5,6-tetramethylnitrobenzene (3463-36-3) + 1,1',2,3',4,4',5-(heptamethyldiphenyl)methane (23946-68-1) + 2,4,5-trimethyl-benzyl alcohol (4393-05-9)

Conditions	Yield
With tetranitromethane In various solvent(s) at 20℃; for 0.5h; Irradiation; Further byproducts given;	A 8.8% B 60% C 4.5% D 10.2%

mesitylglyoxylic acid (3112-46-7) + methyl methacrylate (97-63-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + C16H20O3

Conditions	Yield
With 2,6-dimethylpyridine; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; Co(dmgBF2)2(H2O)2 In acetonitrile at 20℃; Inert atmosphere; Sealed tube; Irradiation;	A 34% B 55%

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 1,1',2,3',4,4',5-(heptamethyldiphenyl)methane (23946-68-1) + (2,4,5-trimethylphenyl)nitromethane (60368-03-8) + 2,4,5-Trimethylbenzyl nitrate (60367-99-9)

Conditions	Yield
With dinitrogen tetraoxide In dichloromethane at 25℃; for 1.5h; Further byproducts given;	A 1% B 3% C 41% D 49%

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,3,5,6-tetramethylnitrobenzene (3463-36-3) + 1,1',2,3',4,4',5-(heptamethyldiphenyl)methane (23946-68-1) + (2,4,5-trimethylphenyl)nitromethane (60368-03-8)

Conditions	Yield
With dinitrogen tetraoxide In dichloromethane at 25℃; for 1.5h; Further byproducts given;	A 1% B 4% C n/a D 41%
With dinitrogen tetraoxide In various solvent(s) at -78℃; for 48h; Irradiation; Further byproducts given;	A 1% B 20% C 8% D 12%
With dinitrogen tetraoxide In dichloromethane at 25℃; Product distribution; Mechanism; Quantum yield; further polymethylarenes, other solvent and temperatures, also in the presence of Lewis acid or under photochemical nitration conditions;

3,4-dimethylbenzaldehyde (5973-71-7) + potassium trifluoro(methyl)boranuide → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With palladium diacetate; 1-fluoro-2,4,6-trimethylpyridin-1-ium tetrafluoroborate; trifluoroacetic acid at 90℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;	37%

carbon monoxide (201230-82-2) + 1,3,5-trimethyl-benzene (108-67-8) → mesytaldehyde (487-68-3) + 2,4,5-trimethylbenzaldehyde (5779-72-6) + 3-Formyl-2,4,6-trimethylbenzenesulfonyl fluoride (139650-07-0)

Conditions	Yield
With antimony pentafluoride; fluorosulphonic acid at 0℃; under 760 Torr; for 48h; Yields of byproduct given;	A n/a B n/a C 34%

carbon monoxide (201230-82-2) + 1,2,3-trimethylbenzene (526-73-8) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,3,4-trimethylbenzaldehyde (34341-28-1) + 2,3,4-Trimethylbenzesulfonyl fluoride (87589-10-4) + 5-Formyl-2,3,4-trimethylbenzenesulfonyl fluoride

Conditions	Yield
With antimony pentafluoride; fluorosulphonic acid at 0℃; for 1h; Yields of byproduct given;	A n/a B n/a C n/a D 25%
With antimony pentafluoride; fluorosulphonic acid at 0℃; for 1h; Product distribution; various SbF5 concentrations;
With antimony pentafluoride; fluorosulphonic acid at 0℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1,2,4,5-tetramethylbenzene (95-93-2) + acetonitrile (75-05-8) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 1,1'-(1,2-ethanediyl)bis-(2,4,5-trimethylbenzene) (18779-88-9) + N-(2,4,5-trimethyl-benzyl)-acetamide (10519-73-0) + 3-(2,4,5-Trimethylphenyl)propanonitrile

Conditions	Yield
With titanium(IV) oxide; silver sulfate for 6h; Ambient temperature; Irradiation; TiO2-photosensitized oxidation;	A 3% B 16% C 7% D 23%

1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,4,5-trimethyl-benzyl alcohol (4393-05-9) + 2,4,5-trimethylbenzoic acid (528-90-5)

Conditions	Yield
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate In acetic acid at 25℃; under 760 Torr; for 3h;	A 17% B 11% C 6%

para-xylene (106-42-3) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,4-dimethylbenzaldehyde (15764-16-6)

Conditions	Yield
With sodium cyanide; aluminium trichloride at 95 - 100℃; Einleiten von HCl und Eintragen des Reaktionsgemisches in Eis und wss. HCl;

1,2,4-Trimethylbenzene (95-63-6) → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With zinc(II) cyanide; aluminium trichloride; benzene at 40 - 45℃; Einleiten von HCl und Behandeln des Reaktionsgemisches mit wss. HCl;
With trifluorormethanesulfonic acid In ice-water

hexamethylenetetramine (100-97-0) + 2,4,5-trimethylbenzyl chloride (10340-77-9) → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With formaldehyd; ethanol

β-chloro-2,4,5-trimethyl-styrene → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
bei der Oxydation; 52-chloro-1.2.4-trimethyl-5-vinyl-benzene;

2,4,5-trimethyl-benzoic acid-(N-methyl-anilide) (857536-54-0) → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride

m-xylene (108-38-3) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 2,4-dimethylbenzaldehyde (15764-16-6)

Conditions	Yield
With sodium cyanide; aluminium trichloride at 95 - 100℃; Einleiten von HCl und Eintragen des Reaktionsgemisches in Eis und wss. HCl;

3,4,6-trimethyl-3-cyclohexene-1-carbaldehyde (13702-58-4) → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With sulfur at 220 - 230℃;
With 5percentPd-5percentFeOx/SiO2 In toluene at 260℃; for 12h; Reagent/catalyst;

4,5-Dimethyl-2-benzyloxymethyl-cyclohexa-1,4-dien-1-carbaldehyd (94823-92-4) → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With toluene-4-sulfonic acid In xylene

2,4,5-Trimethylbenzyl nitrate (60367-99-9) → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With sulfuric acid; acetic acid Heating;

C17H21N3O → 2,4,5-trimethylbenzaldehyde (5779-72-6)

Conditions	Yield
With sulfuric acid; benzene-1,2-dicarboxylic acid In ethylene glycol

naphthalene (91-20-3) + 1,2,4,5-tetramethylbenzene (95-93-2) → 2,4,5-trimethylbenzaldehyde (5779-72-6) + 1,1',2,3',4,4',5-(heptamethyldiphenyl)methane (23946-68-1) + 2,4,5-trimethylbenzylnaphthalene + 2-(2,4,5-Trimethyl-benzyl)-naphthalene

Conditions	Yield
With sulfuric acid In water; acetic acid at 90℃; for 3h; Product distribution; Mechanism;	A 7 % Chromat. B 6 % Chromat. C n/a D n/a

2,4,5-trimethylbenzaldehyde (5779-72-6) → 2,4,5-trimethyl-benzyl alcohol (4393-05-9)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 16h; Inert atmosphere;	100%
Multi-step reaction with 2 steps 1: zinc; aqueous acetic acid 2: aq.-ethanolic NaOH View Scheme

2,4,5-trimethylbenzaldehyde (5779-72-6) → 3-bromo-2,4,5-trimethylbenzaldehyde (485814-90-2)

Conditions	Yield
Stage #1: 2,4,5-trimethylbenzaldehyde With aluminum (III) chloride In dichloromethane at 0 - 20℃; Stage #2: With bromine In dichloromethane at 20℃; for 4h;	100%
With aluminum (III) chloride; bromine In dichloromethane at 20℃; for 4h;	100%

2,4,5-trimethylbenzaldehyde (5779-72-6) + (E)-2,4-dimethyl-6-(4-methylstyryl)aniline → 5,7-dimethyl-3-(4-methylbenzyl)-2-(2,4,5-trimethylphenyl)-1H-indole

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); ethanol; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 120℃; for 6h; Inert atmosphere; regioselective reaction;	94%

2,4,5-trimethylbenzaldehyde (5779-72-6) + (E)-2,4-dimethyl-6-styrylaniline (132589-34-5) → 3-benzyl-5,7-dimethyl-2-(2,4,5-trimethylphenyl)-1H-indole

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); ethanol; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 120℃; for 3h; Inert atmosphere; regioselective reaction;	94%

2,4,5-trimethylbenzaldehyde (5779-72-6) + (E)-2-methyl-6-(4-methylstyryl)aniline → 7-methyl-3-(4-methylbenzyl)-2-(2,4,5-trimethylphenyl)-1H-indole

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); ethanol; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 120℃; for 3h; Inert atmosphere; regioselective reaction;	93%

2,4,5-trimethylbenzaldehyde (5779-72-6) + 1-bromo-2,4,5-trimethylbenzene (5469-19-2) → bis(2,4,5-trimethylphenyl)methanol (871896-64-9)

Conditions	Yield
Stage #1: 1-bromo-2,4,5-trimethylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2,4,5-trimethylbenzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 6h; Inert atmosphere;	92.8%

2,4,5-trimethylbenzaldehyde (5779-72-6) + N-phenylacetoacetamide (102-01-2) + ethyl 2-cyanoacetate (105-56-6) → C23H23N3O2

Conditions	Yield
With ammonium acetate In ethanol at 50℃; Microwave irradiation; Green chemistry;	91%

2,4,5-trimethylbenzaldehyde (5779-72-6) → 1,2,4,5-benzenetetracarboxylic acid (89-05-4)

Conditions	Yield
Stage #1: 2,4,5-trimethylbenzaldehyde With air at 220℃; under 24002.4 Torr; Stage #2: With air at 220℃; under 21752.2 Torr;	82.4%
With oxygen; oxidation catalyst In water at 180 - 280℃; under 11251.1 - 45004.5 Torr;
With potassium permanganate; sodium hydroxide In water at 100℃; for 8h; Reagent/catalyst; Temperature;

2-acetylpyridine (1122-62-9) + 2,4,5-trimethylbenzaldehyde (5779-72-6) → C17H17NO

Conditions	Yield
With sodium hydroxide In methanol; water at 0 - 20℃; Kroehnke Pyridine Synthesis;	79%

2,4,5-trimethylbenzaldehyde (5779-72-6) → (E)-2,2',4,4',5,5'-hexamethylstilbene (138151-98-1)

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran for 16h; Heating;	74%
With titanium tetrachloride; zinc In tetrahydrofuran for 17h; Heating;

tert-butylisonitrile (119072-55-8, 7188-38-7) + 2,4,5-trimethylbenzaldehyde (5779-72-6) + 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (152460-10-1) → N1-[(1-(tert-butyl)-1H-tetrazol-5-yl)(2,4,5-trimethylphenyl)methyl]-4-methyl-N3-[4-(pyridin-3-yl)pyrimidin-2-yl]-benzene-1,3-diamine

Conditions	Yield
With trimethylsilylazide In methanol at 95℃; for 0.166667h; Ugi Condensation; Microwave irradiation; Sealed tube;	73%

Cyclohexyl isocyanide (931-53-3) + 2,4,5-trimethylbenzaldehyde (5779-72-6) + 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (152460-10-1) → N1-[(1-cyclohexyl-1H-tetrazol-5-yl)(2,4,5-trimethylphenyl)-methyl]-4-methyl-N3-[4-(pyridin-3-yl)pyrimidin-2-yl]-benzene-1,3-diamine

Conditions	Yield
With trimethylsilylazide In methanol at 95℃; for 0.166667h; Ugi Condensation; Microwave irradiation; Sealed tube;	70%

tert-butylisonitrile (119072-55-8, 7188-38-7) + trimethylsilylazide (4648-54-8) + 2,4,5-trimethylbenzaldehyde (5779-72-6) + Propargylamine (2450-71-7) → N-((1-(tert-butyl)-1H-tetrazol-5-yl)(2,4,5-trimethylphenyl)methyl)prop-2-yn-1-amine

Conditions	Yield
In neat (no solvent) at 20℃; for 24h; Ugi Condensation;	70%

2,4,5-trimethylbenzaldehyde (5779-72-6) + phenylacetylene (536-74-3) → 1-(2,4,5-trimethylphenyl)-3-phenylprop-2-yn-1-ol

Conditions	Yield
With titanium(IV) isopropylate; diethylzinc; (S)-3,3'-bis(morpholinomethyl)-2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl In tetrahydrofuran at 20℃; for 4h;	68%
With titanium(IV) isopropylate; diethylzinc; (S)-3,3'-bis(morpholinomethyl)-2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl In tetrahydrofuran at 20℃; for 4h;	68%

2,4,5-trimethylbenzaldehyde (5779-72-6) + acetic acid (64-19-7) → C12H14O3

Conditions	Yield
With dipotassium peroxodisulfate; water; palladium diacetate; acetic acid hydrazide at 110℃; for 48h; Molecular sieve;	64%

ethyl (E)-3-iodopropenoate (31930-36-6, 31930-37-7) + 2,4,5-trimethylbenzaldehyde (5779-72-6) → C15H20O3

Conditions	Yield
With chromium chloride; manganese; chloro-trimethyl-silane; nickel dichloride In tetrahydrofuran at 0℃; for 36h; enantioselective reaction;	62%

2,4,5-trimethylbenzaldehyde (5779-72-6) + (E)-4-methoxy-2-(4-methylstyryl)aniline → 5-methoxy-3-(4-methylbenzyl)-2-(2,4,5-trimethylphenyl)-1H-indole

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); ethanol; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 120℃; for 3h; Inert atmosphere; regioselective reaction;	61%

2,4,5-trimethylbenzaldehyde (5779-72-6) + (E)-4-methyl-2-(4-methylstyryl)aniline → 5-methyl-3-(4-methylbenzyl)-2-(2,4,5-trimethylphenyl)-1H-indole

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); ethanol; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 120℃; for 6h; Inert atmosphere; regioselective reaction;	60%

2,4-imidazolidinedione (461-72-3) + 2,4,5-trimethylbenzaldehyde (5779-72-6) → 5-[1-(2,4,5-Trimethyl-phenyl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione

Conditions	Yield
With sodium hydrogencarbonate; ethanolamine In ethanol at 120℃; pH=7.0;	58.5%

2-iodonaphthalene (612-55-5) + 2,4,5-trimethylbenzaldehyde (5779-72-6) → 9,10-dimethyl-1,2-benzanthracene (58429-99-5)

Conditions	Yield
With trifluorormethanesulfonic acid; palladium diacetate; silver trifluoroacetate; acetic acid; glycine at 100℃; for 24h; Sealed tube;	58%

Upstream product

• 857536-54-0 2,4,5-trimethyl-benzoic acid-(N-methyl-anilide) 
• 33070-58-5 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide 
• 95-93-2 1,2,4,5-tetramethylbenzene 
• 64-19-7 acetic acid 
• 75-05-8 acetonitrile 
• 201230-82-2 carbon monoxide 
• 95-63-6 1,2,4-Trimethylbenzene 
• 526-73-8 1,2,3-trimethylbenzene 
• 108-67-8 1,3,5-trimethyl-benzene 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 106-42-3 para-xylene 
• 143-33-9 sodium cyanide 
• 13702-58-4 trans-1,2,4-trimethyl-5-formylcyclohex-1-ene 

Downstream Products

• 97023-14-8 4-<2.4.5-Trimethyl-phenyl>-buten-(3)-on-(2) 
• 75279-58-2 (2,4,5-trimethyl-phenyl)-acetonitrile 
• 4393-05-9 2,4,5-trimethyl-benzyl alcohol 
• 3167-01-9 (2,4,5-trimethyl-phenyl)-acetic acid 
• 10340-77-9 2,4,5-trimethylbenzyl chloride 
• 544697-03-2 (2,4,5-trimethyl-3,6-dinitro-phenyl)-acetic acid 
• 89-05-4 1,2,4,5-benzenetetracarboxylic acid 
• 34240-10-3 5-methyl-1,2,4-benzenetricarboxylic acid 
• 528-44-9 1,2,4-benzene tricarboxylic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 4957-16-8 2,2,4,4',5,5'-hexamethyldiphenylmethane 
• 5766-30-3 bis(2,4,5-trimethylphenyl)methanone 
• 871896-64-9 bis(2,4,5-trimethylphenyl)methanol 
• 97115-92-9 1,4-Di-(2,4,5-trimethyl-phenyl)-1,4-dihydroxy-butin-⁽²⁾ 

Relevant articles and documents

A Desaturative Approach for Aromatic Aldehyde Synthesis via Synergistic Enamine, Photoredox and Cobalt Triple Catalysis

Aromatic aldehydes are fundamental intermediates that are widely utilised for the synthesis of important materials across the broad spectrum of chemical industries. Accessing highly substituted derivatives can often be difficult as their functionalizations are generally performed via electrophilic aromatic substitution, SEAr. Here we provide an alternative and mechanistically distinct approach whereby aromatic aldehydes are assembled from saturated precursors via a desaturative process. This novel strategy harnesses the high-fidelity of Diels–Alder cycloadditions to quickly construct multi-substituted cyclohexenecarbaldehyde cores which undergo desaturation via the synergistic interplay of enamine, photoredox and cobalt triple catalysis.

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Methods for preparing benzene-ring-containing compounds from pinacol

The invention relates to methods for preparing durene, 1,2,3-trimethylbenzene, o-xylene, pyromellitic acid and trimellitic acid from pinacol. Durene, 1,2,3-trimethylbenzene and o-xylene are prepared through three steps of reaction, and pyromellitic acid and trimellitic acid are prepared through four steps of reaction. A catalytic system used in the invention is green and environment-friendly, andcan be recycled. The raw materials of method, i.e., pinacol, crotonaldehyde, acrolein and crotonate can all be derived from biomass, and are cheap and easily available. All the reaction processes aresimple and are high in activity and selectivity in the dehydration of pinacol and the dehydrogenation, decarbonylation and oxidation of D-A products. The invention provides novel methods for preparingfine chemicals including durene, 1,2,3-trimethylbenzene, o-xylene, pyromellitic acid and trimellitic acid from lignocellulose-based platform chemicals.