4925-88-6

Basic information

• Product Name: 2,5-DIMETHOXY-4-METHYLBENZALDEHYDE
• Synonyms: 2,5-DiMethoxy-p-tolualdehyde;4-Methyl-2,5-diMethoxybenzaldehyde;Benzaldehyde, 2,5-diMethoxy-4-Methyl-
• CAS NO: 4925-88-6
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 4925-88-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: 82-86℃
• Boiling Point: 307.5°C at 760 mmHg
• Flash Point: 130.7°C
• Appearance: Off-white/Solid
• Density: 1.089g/cm³
• Vapor Pressure: 0.000723mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Soluble in dichloromethane, dimethyl sulfoxide and methanol. Slightly soluble in water.
• CAS DataBase Reference: 2,5-DIMETHOXY-4-METHYLBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHOXY-4-METHYLBENZALDEHYDE(4925-88-6)
• EPA Substance Registry System: 2,5-DIMETHOXY-4-METHYLBENZALDEHYDE(4925-88-6)

Safety Data

• Hazardous Substances Data: 4925-88-6(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

2,5-Dimethoxy-4-methylbenzaldehyde is used in the preparation of phenylamine derivative as potential psychotomimetics.

InChI:InChI=1/C10H12O3/c1-7-4-10(13-3)8(6-11)5-9(7)12-2/h4-6H,1-3H3

Synthetic route

2,5-dimethoxy toluene (24599-58-4) + N-methyl-N-phenylformamide (93-61-8) → 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6)

Conditions	Yield
Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 20℃; for 0.833333h; Inert atmosphere; Stage #2: 2,5-dimethoxy toluene at 70℃; for 1h; Inert atmosphere;	86%
Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 20℃; for 0.666667h; Stage #2: 2,5-dimethoxy toluene at 50℃; for 6h; Stage #3: With sodium acetate; sodium hydrogensulfite more than 3 stages;	67%
(i) POCl3, (ii) /BRN= 2045336/; Multistep reaction;
With trichlorophosphate at 0 - 80℃; for 1h;
Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 20℃; for 4h; Stage #2: 2,5-dimethoxy toluene at 70℃; for 2h;

2,5-dimethoxy toluene (24599-58-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6)

Conditions	Yield
With trichlorophosphate at 80℃; for 8h;	85.9%
With trichlorophosphate In 1,2-dichloro-ethane at 80℃; for 12h; Vilsmeier-Haack formylation;	80%
With trichlorophosphate at 60℃; for 24h; Formylation;

2,5-dihydroxy-4-methylbenzaldehyde (52010-89-6) + methyl iodide (74-88-4) → 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 18h;	80%
With potassium carbonate In acetone at 25℃; for 20h;

2-(2,5-dimethoxy-4-methyl-phenyl)-[1,3]dioxolane (246543-82-8) → 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + 2-[1,3]dioxolan-2-yl-5-methyl-[1,4]benzoquinone

Conditions	Yield
With cobalt (III) fluoride In acetonitrile at 20℃; for 0.416667h; Oxidation; Demethylation;	A 20% B 55%

Dichloromethyl methyl ether (4885-02-3) + 2,5-dimethoxy toluene (24599-58-4) → 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6)

Conditions	Yield
With tin(IV) chloride 1.) CH2Cl2, 0 deg C, 1 h, 2.) CH2Cl2, a) 0 deg C, 30 min, b) RT, 1 h; Yield given. Multistep reaction;
Stage #1: 2,5-dimethoxy toluene With titanium tetrachloride In dichloromethane at 20℃; for 2h; Inert atmosphere; Cooling with ice; Stage #2: Dichloromethyl methyl ether In dichloromethane at 20℃; for 2.5h; Inert atmosphere; Cooling with ice;	9.1 g

2,5-dimethoxy toluene (24599-58-4) + dicyanozinc (557-21-1) → 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6)

Conditions	Yield
With hydrogenchloride; aluminium trichloride; sulfuric acid 1) tetrachloroethane, 8 h, 65-70 deg C 2) overnight, room temperature 3) steam distillation; Yield given. Multistep reaction;

2,5-dimethoxy-4-methylphenylmethanol (32176-96-8) → 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6)

Conditions	Yield
With selenium(IV) oxide

2-methylbenzene-1,4-diol (95-71-6) → 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / potassium hydroxide / methanol / 8 h / steam distillation 2: 1) HCl, aluminium chloride 2) aqueous H2SO4 / 1) tetrachloroethane, 8 h, 65-70 deg C 2) overnight, room temperature 3) steam distillation View Scheme

phosphorous oxychloride (POCl3) + 2,5-dimethoxy toluene (24599-58-4) + N-methyl-N-phenylformamide (93-61-8) → 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6)

Conditions	Yield
In water

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 2-hydroxy-4-methyl-5-methoxybenzaldehyde (74516-54-4)

Conditions	Yield
With aluminium trichloride; sodium iodide In acetonitrile for 2h; Heating;	99%
With boron trichloride In dichloromethane at -78 - 20℃;	65%
Stage #1: 2,5-dimethoxy-4-methylbenzaldehyde With aluminum (III) chloride; sodium iodide In acetonitrile at 80℃; for 1h; Stage #2: With water In acetonitrile at 0℃;

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 2,5-dihydroxy-4-methylbenzaldehyde (52010-89-6)

Conditions	Yield
With boron tribromide In dichloromethane at -78℃; for 8h;	99%
With boron tribromide In dichloromethane at -78℃; for 24h;	87%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 2,5-dimethoxy-4-methylphenol

Conditions	Yield
Stage #1: 2,5-dimethoxy-4-methylbenzaldehyde With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at -10℃; for 1h; Inert atmosphere; Stage #2: With potassium hydroxide In methanol at 20℃; for 0.5h; Inert atmosphere;	98%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → C10H13NO3 (32230-29-8)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol at 20℃; for 18h;	92%
With hydroxylamine hydrochloride; sodium acetate In methanol at 25℃; for 2h;

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + 2',5'-dimethoxyacetophenone (1201-38-3) → 3-(2',5'-dimethoxy-4-methylphenyl)-1-(2,5-dimethoxyphenyl)-2-propenone

Conditions	Yield
With sodium hydroxide In methanol for 5h; Heating;	91%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 2,5-dimethoxy-4-methylphenylmethanol (32176-96-8)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In tetrahydrofuran; water for 0.5h; Ambient temperature;	85%
With sodium hydroxide; sodium tetrahydroborate; water In tetrahydrofuran at 20℃; for 0.5h; Reduction;

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + cyclopropyldiphenylsulfonium tetrafluoroborate (33462-81-6) → 2-(2,5-dimethoxy-4-methylphenyl)cyclobutanone (90791-16-5)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0℃; for 2h;	84%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + aniline (62-53-3) → (E)-2,5-dimethoxy-4-methyl-N-phenylbenzaldimin

Conditions	Yield
	84%

cycl-isopropylidene malonate (2033-24-1) + 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 5-(2,5-Dimethoxy-4-methyl-benzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (117646-12-5)

Conditions	Yield
In N,N-dimethyl-formamide for 12h; Ambient temperature;	83%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + 4,6-dinitro-m-xylene (616-72-8) → (E,E)-1,3-bis(2,5-dimethoxy-4-methylstyryl)-4,6-dinitrobenzene

Conditions	Yield
With piperidine for 0.15h; microwave irradiation;	82%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + allylmagnesium bromide (1730-25-2) → 1-(2,5-dimethoxy-4-methylphenyl)but-3-en-1-ol (1254593-04-8)

Conditions	Yield
Stage #1: 2,5-dimethoxy-4-methylbenzaldehyde; allylmagnesium bromide In diethyl ether for 2.5h; Stage #2: With water; ammonium chloride In diethyl ether	81%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + vinylmagnesium chloride (3536-96-7) → 1-(2,5-dimethoxy-4-methylphenyl)prop-2-en-1-ol

Conditions	Yield
In tetrahydrofuran at 0℃; for 1.5h;	81%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + methyl (triphenylphosphoranylidene)acetate (21204-67-1) → C13H16O4

Conditions	Yield
In benzene for 4h; Wittig-Horner olefination; Reflux;	80%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + cyclopropyldiphenylsulfonium triflate (116808-70-9) → 2-(2,5-dimethoxy-4-methylphenyl)cyclobutanone (90791-16-5)

Conditions	Yield
Stage #1: 2,5-dimethoxy-4-methylbenzaldehyde; cyclopropyldiphenylsulfonium triflate With potassium tert-butylate In tetrahydrofuran at -15 - 20℃; for 3h; Stage #2: With tetrafluoroboric acid In tetrahydrofuran at 20℃; for 3h;	80%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 1,4-dimethoxy-2-methyl-5-nitrobenzene (32185-64-1) + 3,6-dimethoxy-4-methyl-2-nitrobenzaldehyde

Conditions	Yield
With nitric acid In dichloromethane at 20℃; for 24h;	A 80% B 5%

Nitroethane (79-24-3) + 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 1-(2,5-Dimethoxy-4-methyl-phenyl)-2-nitro-1-propan (143823-25-0) + 2,5-dimethoxy-4-methyl-benzonitrile (51267-09-5)

Conditions	Yield
With ammonium acetate In acetic acid at 50℃; under 7500600 Torr; for 3h;	A 78% B n/a

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + 1-Nitropropane (108-03-2) → 1,4-Dimethoxy-2-methyl-5-((E)-2-nitro-but-1-enyl)-benzene (134573-08-3) + 2,5-dimethoxy-4-methyl-benzonitrile (51267-09-5)

Conditions	Yield
With ammonium acetate In acetic acid at 50℃; under 7500600 Torr; for 3h;	A 74% B n/a

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + 1-Nitropropane (108-03-2) → 1-(2,5-dimethoxy-4-methylphenyl)-2-nitro-1-butene

Conditions	Yield
With ammonium acetate for 20h; Heating;	72%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 4-methyl-2,5-dimethoxy-benzoic acid (32176-94-6)

Conditions	Yield
With potassium permanganate In water at 75℃; for 2h;	71%
Stage #1: 2,5-dimethoxy-4-methylbenzaldehyde With potassium permanganate In water at 75℃; for 2h; Stage #2: With sodium hydroxide In water pH=10;	71%
With dihydrogen peroxide; potassium hydroxide In water at 65℃; for 24.3333h;	70%
With potassium permanganate
With sodium chlorite; aminosulfonic acid In water; acetone for 1.5h; Cooling with ice;	6.36 g

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + 2-(2-iodophenyl)acetonitrile (40400-15-5) → 2-(2,5-dimethoxy-4-methylphenyl)benzofuran-3-carbonitrile

Conditions	Yield
With copper(l) iodide; 4,7-Dimethyl-1,10-phenanthroline; caesium carbonate In dimethyl sulfoxide at 90℃; for 36h; regioselective reaction;	70%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + Dimethyl succinate (106-65-0) → (E)-3-methoxycarbonyl-4-(2,5-dimethoxy-4-methylphenyl)but-3-enoic acid (97944-74-6)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol for 13.5h; Heating;	62%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + 2-bromoaniline (615-36-1) + 3-(2-nitroethenyl)-1H-indole (3156-51-2) → 8-bromo-2-(2,5-dimethoxy-4-methylphenyl)-4-(1H-indol-3-yl)-3-nitro-1,2,3,4-tetrahydroquinoline

Conditions	Yield
Stage #1: 2,5-dimethoxy-4-methylbenzaldehyde; 2-bromoaniline With iron(III) chloride In 1,2-dichloro-ethane for 0.166667h; Reflux; Stage #2: 3-(2-nitroethenyl)-1H-indole In 1,2-dichloro-ethane for 56h; Reflux;	43%

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → (E)-1,2-bis(2,5-dimethoxy-p-tolyl)ethene (21071-42-1)

Conditions	Yield
With titanium(III) chloride; lithium In 1,2-dimethoxyethane for 16h; Heating;	34%

Nitroethane (79-24-3) + 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 1-(2,5-Dimethoxy-4-methyl-phenyl)-2-nitro-1-propan (143823-25-0)

nitromethane (75-52-5) + 2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) → 2,5-Dimethoxy-4-methyl-β-nitrostyrol (25505-64-0)

2,5-dimethoxy-4-methylbenzaldehyde (4925-88-6) + N-acetylglycine (543-24-8) → 4-(2,5-dimethoxy-4-methyl-benzylidene)-2-methyl-4H-oxazol-5-one (35264-88-1)

Conditions	Yield
With sodium acetate In acetic anhydride Heating;

Upstream product

• 4885-02-3 Dichloromethyl methyl ether 
• 24599-58-4 2,5-dimethoxy toluene 
• 557-21-1 dicyanozinc 
• 32176-96-8 2,5-dimethoxy-4-methylphenylmethanol 
• 93-61-8 N-methyl-N-phenylformamide 
• 68-12-2 N,N-dimethyl-formamide 
• 246543-82-8 2-(2,5-dimethoxy-4-methyl-phenyl)-[1,3]dioxolane 
• 95-71-6 2-methylbenzene-1,4-diol 
• 52010-89-6 2,5-dihydroxy-4-methylbenzaldehyde 
• 74-88-4 methyl iodide 

Downstream Products

• 143823-25-0 1-(2,5-Dimethoxy-4-methyl-phenyl)-2-nitro-1-propan 
• 25505-64-0 2,5-Dimethoxy-4-methyl-β-nitrostyrol 
• 29907-72-0 1-(2,5-Dimethoxy-4-methyl-phenyl)-2-nitro-propen 
• 51267-09-5 2,5-dimethoxy-4-methyl-benzonitrile 
• 81129-26-2 (Z)-1,4-dimethoxy-2-methyl-5-(prop-1-en-1-yl)benzene 
• 81129-27-3 (E)-1,4-dimethoxy-2-methyl-5-(prop-1-en-1-yl)benzene 
• 90791-16-5 2-(2,5-dimethoxy-4-methylphenyl)cyclobutanone 
• 87050-71-3 4,4'-Dimethyl-2,2',5,5'-tetramethoxy-stilben 
• 21071-42-1 (E)-1,2-bis(2,5-dimethoxy-p-tolyl)ethene 
• 32176-96-8 2,5-dimethoxy-4-methylphenylmethanol 
• 32185-64-1 1,4-dimethoxy-2-methyl-5-nitrobenzene 
• 74516-54-4 2-hydroxy-4-methyl-5-methoxybenzaldehyde 
• 52807-48-4 1,4-Dimethoxy-2-methyl-5-((E)-2-nitro-but-1-enyl)-benzene 
• 180578-78-3 (E)-1-(2,5-dimethoxy-4-methylphenyl)-2-pentamethylphenylethene 

Relevant articles and documents

Seven-membered ring compound and application thereof in prevention and treatment of diabetes and metabolic syndrome

The invention discloses a seven-membered ring compound and application thereof in prevention and treatment of diabetes and metabolic syndrome. The structure of the seven-membered ring compound is as shown in a general formula I, and definitions of substituent groups are as shown in the specification and claims. The seven-membered ring compound of the invention has an extremely excellent effect ofpreventing or treating diabetes and metabolic syndrome.

LIPIDS AND LIPID COMPOSITIONS FOR THE DELIVERY OF ACTIVE AGENTS

This invention provides for a compound of formula (I), or a pharmaceutically acceptable salt thereof, wherein RA, RB, R2 and R4 are defined herein. The compounds of formula (I) and pharmaceutically acceptable salts thereof are cationic lipids useful in the delivery of biologically active agents to cells and tissues.

Synthesis of novel isoxazole-benzoquinone hybrids via 1,3-dipolar cycloaddition reaction as key step

An efficient method for the preparation of novel 2-(5-arylisoxazol-3-yl) cyclohexa-2,5-diene-1,4-dione hybrids via 1,3-dipolar cycloaddition followed by an oxidation reaction using ceric ammonium nitrate (CAN) has been described. Using this method, various aryl as well as alkyl substituted isoxazole-benzoquinone hybrids were synthesized in high yields.