86-51-1

Basic information

• Product Name: 2,3-Dimethoxybenzaldehyde
• Synonyms: LABOTEST-BB LT00932325;BENZALDEHYDE, 2,3-DIMETHOXY-;O-VERATRALDEHYDE;O-VERATRIC ALDEHYDE;3,5-Dihydroxypropiophenone;3,5-Dimethylsalicylic acid;4-Diethoxybenzene;2,3-Dimethoxybenzenecarbonal
• CAS NO: 86-51-1
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 201-677-7
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);BenzaldehydeDerivative;Benzaldehyde;Aldehydes;C9;Carbonyl Compounds;Aromatics;Miscellaneous Reagents;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Inhibitors
• Mol File: 86-51-1.mol
• Article Data: 58

Chemical Properties

• Melting Point: 48-52 °C(lit.)
• Boiling Point: 137 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Off-white to beige/Crystalline Powder, Crystals, and/or Chunks
• Density: 1.1708 (rough estimate)
• Vapor Pressure: 0.00849mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Solubility in methanol with almost transparency.
• Sensitive: Air Sensitive
• BRN: 908264
• CAS DataBase Reference: 2,3-Dimethoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethoxybenzaldehyde(86-51-1)
• EPA Substance Registry System: 2,3-Dimethoxybenzaldehyde(86-51-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CU5732000
• Hazardous Substances Data: 86-51-1(Hazardous Substances Data)

Usage

Chemical Properties

white to brown crystalline powder

Uses

Different sources of media describe the Uses of 86-51-1 differently. You can refer to the following data:
1. A benzaldehyde derivative that may possess antifungal activity of redox-active benzaldehydes that target cellular antioxidation. It could function as chemosensitizing agents in concert with convention al drugs or fungicides to improve antifungal efficacy.
2. 2,3-Dimethoxybenzaldehyde possess antifungal activity of redox-active benzaldehydes that target cellular antioxidation. It could function as chemosensitizing agents in concert with conventional drugs to improve antifungal efficacy.

Safety Profile

A poison by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors

InChI:InChI=1/C9H10O3/c1-11-8-5-3-4-7(6-10)9(8)12-2/h3-6H,1-2H3

Synthetic route

2,3-dimethoxybenzyl alcohol (5653-67-8) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With aluminium trichloride; 1-decyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate In acetonitrile for 1.4h; Heating;	99%
With benzyltriphenylphosphonium dichromate In acetonitrile for 0.333333h; Oxidation; Heating;	98%
With benzyltriphenylphosphonium chlorochromate In dichloromethane for 0.0333333h; Oxidation; microwave irradiation;	98%

3-methoxy-2-hydroxybenzaldehyde (148-53-8) + methyl iodide (74-88-4) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 42h;	99%
Stage #1: 3-methoxy-2-hydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃;
Stage #1: 3-methoxy-2-hydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃;
Stage #1: 3-methoxy-2-hydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃;

3-methoxy-2-hydroxybenzaldehyde (148-53-8) + dimethyl sulfate (77-78-1) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With potassium carbonate In benzene	98.7%
With potassium carbonate In methanol for 2.5h; Heating;	93%
With potassium carbonate In benzene for 26h; Heating;	89%

formaldehyd (50-00-0) + 1,2-dimethoxybenzene (91-16-7) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With triethylamine; magnesium chloride In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 6h;	94.4%

1-(bis-ethylsulfanyl-methyl)-2,3-dimethoxy-benzene → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In dichloromethane; water at 20℃; for 0.166667h;	90%

2,3-dihydroxybenzaldehyde (24677-78-9) + dimethyl sulfate (77-78-1) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
Stage #1: 2,3-dihydroxybenzaldehyde With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: dimethyl sulfate In acetone at 20℃; for 5h;	89%
With sodium hydroxide In water for 1h; Heating;	68%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + 2,3-dimethoxyphenyl triflate (213479-69-7) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 25℃; for 16h; Schlenk technique; Inert atmosphere;	83%
With triethylsilane; potassium acetate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 50℃; for 12h; Schlenk technique; Inert atmosphere; Molecular sieve;	72%

formic acid (64-18-6) + 1-iodo-2,3-dimethoxybenzene (25245-33-4) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 4h; Sealed tube;	82%

1,2-Dimethoxy-3-phenethyloxymethyl-benzene (121336-26-3) → 2-phenylethanol (60-12-8) + 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 12.5h;	A 75% B 73%

2,3-dihydroxybenzaldehyde (24677-78-9) + methyl iodide (74-88-4) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;	73%

2,3-dihydroxybenzaldehyde (24677-78-9) + methyl iodide (74-88-4) → 3-hydroxy-2-methoxybenzaldehyde (66495-88-3) + 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
Stage #1: 2,3-dihydroxybenzaldehyde With potassium hydrogencarbonate In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 28h; Inert atmosphere;	A 72% B n/a
Stage #1: 2,3-dihydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 18h;	A 57% B 19%
Stage #1: 2,3-dihydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 18h;	A 57% B 19%
With sodium hydride In dimethyl sulfoxide at 25℃; for 17h; NaH : pyrocatechlol 1.1; Yields of byproduct given;	A 52% B n/a

1-((2,3-dimethoxybenzyl)oxy)-1H-benzo[d][1,2,3]triazole + 4-nitrophenylboronic acid (24067-17-2) → C15H15NO4 + 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With potassium phosphate; water; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 100℃; for 18h;	A 67% B n/a

2,3-dihydroxybenzaldehyde (24677-78-9) + methyl iodide (74-88-4) → 3-methoxy-2-hydroxybenzaldehyde (148-53-8) + 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 25℃; for 17h; NaH : pyrocatechlol 2.2; Yields of byproduct given;	A 58% B n/a

2-(2,3-dimethoxyphenyl)-2-hydroxyacetonitrile (99060-42-1) → hydrogen cyanide (74-90-8) + 2,3-dimethyoxybenzaldehyde (86-51-1)

1,2-dimethoxy-3-((1E)-prop-1-en-1-yl)benzene (167774-23-4) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With potassium dichromate; sulfuric acid; 4-aminobenzene sulfonic acid
With potassium dichromate; sulfuric acid
With ozone; ethyl acetate at -20℃; und Erhitzen des Reaktionsgemisches mit Wasserdampf;

3-methoxy-2-hydroxybenzaldehyde (148-53-8) + dimethyl sulfate (77-78-1) → 2,3-dimethoxybenzaldehyde dimethylacetal (59276-32-3) + 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With potassium hydroxide

2,3-dimethoxybenzoyl chloride (7169-06-4) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With Pd-BaSO4; xylene at 140℃; Hydrogenation;

meta-hydroxybenzaldehyde (100-83-4) + dimethyl sulfate (77-78-1) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With oxygen; copper; sodium carbonate; copper(I) chloride 1.) CH3CN; Multistep reaction;

2,3-dimethoxybenzoic acid (1521-38-6) → 2,3-dimethoxybenzyl alcohol (5653-67-8) + 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With chloro-trimethyl-silane; diisobutylaluminium hydride; triethylamine 1.) CH2Cl2, 0 deg C; 2.) CH2Cl2, -78 deg C; Yield given. Multistep reaction. Yields of byproduct given;

hydrogenchloride (7647-01-0) + (2-benzo[1,3]dioxol-5-yl-ethyl)-(2,3-dimethoxy-benzyliden)-amine → homopiperonylamine hydrochloride (1653-64-1) + 2,3-dimethyoxybenzaldehyde (86-51-1)

dimethyl sulfate (77-78-1) + alkali salt of 2-oxy-3-methoxy-benzaldehyde → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With alkaline solution

tetrachloromethane (56-23-5) + 2,3-dimethoxybenzoyl chloride (7169-06-4) + palladium-barium sulfate → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
at 140℃; Hydrogenation;

dimethyl sulfate (77-78-1) + sodium salt of 2-oxy-3-methoxy-benzaldehyde → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
With benzene

2-cyano-3t-(2,3-dimethoxy-phenyl)-acrylic acid (91106-58-0) + KOH-solution → 2,3-dimethyoxybenzaldehyde (86-51-1)

2-benzyl-3-(2,3-dimethoxyphenyl)-5-propylcarbamoyl-2,3-dihydroisoxazole-4-carboxylic acid methyl ester (919112-52-0) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
In tetrahydrofuran Heating;

C-(2,3-dimethoxyphenyl)-N-benzyl-nitrone (868775-52-4, 919112-38-2) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 73 percent / benzene / 22 h / 20 °C 2: 37 percent / methanol / 3 h / 20 °C 3: tetrahydrofuran / Heating View Scheme

2-benzyl-3-(2,3-dimethoxyphenyl)-2,3-dihydroisoxazole-4,5-dicarboxylic acid dimethyl ester (919112-44-0) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 37 percent / methanol / 3 h / 20 °C 2: tetrahydrofuran / Heating View Scheme

3-ethoxysalicylaldehyde (492-88-6) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / BBr3 / CHCl3 / 1. 0 deg C, 2.5 h; 2. room temperature, overnight 2: 68 percent / NaOH / H2O / 1 h / Heating View Scheme

2,3-dimethoxybenzoic acid (1521-38-6) → 2,3-dimethyoxybenzaldehyde (86-51-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform; phosphorus pentachloride 2: palladium-barium sulfate; xylene / 140 °C / Hydrogenation View Scheme

methylamine (74-89-5) + 2,3-dimethyoxybenzaldehyde (86-51-1) → (2,3-dimethoxy-benzylidene)-methyl-amine (722495-95-6)

Conditions	Yield
at 20℃; for 12h;	100%
In ethanol at 0 - 40℃;	90%
With benzene zuletzt unter Erwaermen und Entfernen des gebildeten Wassers;
In benzene for 2h; Reflux;
In ethanol; water

2,3-dimethyoxybenzaldehyde (86-51-1) → 2,3-dimethoxybenzyl alcohol (5653-67-8)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 0.166667h;	100%
With sodium tetrahydroborate In ethanol for 20h; Ambient temperature;	99%
With sodium tetrahydroborate In methanol at 20℃; for 1h;	99%

1-Bromotetradecane (112-71-0) + 2,3-dimethyoxybenzaldehyde (86-51-1) → (+/-)-1-hydroxy-1-(2.3-dimethoxy-phenyl)-pentadecane (33597-07-8)

Conditions	Yield
Stage #1: 1-Bromotetradecane With iodine; magnesium In diethyl ether Stage #2: 2,3-dimethyoxybenzaldehyde In diethyl ether for 4h; Reflux;	100%
With lithium In tetrahydrofuran at 0℃;	63%

tert-butylisonitrile (119072-55-8, 7188-38-7) + acetic acid (64-19-7) + 1-amino-2-propene (107-11-9) + 2,3-dimethyoxybenzaldehyde (86-51-1) → 2-(acetylallylamino)-N-tert-butyl-2-(2,3-dimethoxyphenyl)acetamide (956093-06-4)

Conditions	Yield
In methanol at 20℃; for 6h; Ugi reaction;	100%

(S)-1-Aminoindane (10277-74-4, 34698-41-4, 61341-86-4, 61949-83-5) + 2,3-dimethyoxybenzaldehyde (86-51-1) → C18H19NO2

Conditions	Yield
In neat (no solvent, solid phase) Milling;	100%

(R)-1-Aminoindane (10277-74-4) + 2,3-dimethyoxybenzaldehyde (86-51-1) → C18H19NO2

Conditions	Yield
In neat (no solvent, solid phase) Milling;	100%

(S)-1,2,3,4-tetrahydronapht-1-yl-amine (23357-52-0) + 2,3-dimethyoxybenzaldehyde (86-51-1) → C19H21NO2

Conditions	Yield
In neat (no solvent, solid phase) Milling;	100%

(R)-1,2,3,4-Tetrahydro-1-naphthylamine (23357-46-2) + 2,3-dimethyoxybenzaldehyde (86-51-1) → C19H21NO2

Conditions	Yield
In neat (no solvent, solid phase) Milling;	100%

nitromethane (75-52-5) + 2,3-dimethyoxybenzaldehyde (86-51-1) → 1,2-Dimethoxy-3-((E)-2-nitro-vinyl)-benzene (37630-20-9)

Conditions	Yield
With ammonium acetate; acetic acid at 22℃; for 3h; ultrasound;	99%
	81%
With sodium hydroxide In methanol; water for 0.5h; Cooling with ice;	46%

(2-iodo-4,5-dimethoxybenzyl)triphenylphosphonium bromide + 2,3-dimethyoxybenzaldehyde (86-51-1) → 1-(2-(2,3-dimethoxyphenyl)-1-ethenyl)-2-iodo-4,5-dimethoxybenzene

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 16h; Wittig reaction;	99%
Stage #1: (2-iodo-4,5-dimethoxybenzyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran at 20℃; Wittig reaction; Further stages.;	99%

3-bromopropylamine hydrochloride (5003-71-4) + 2,3-dimethyoxybenzaldehyde (86-51-1) → 2,3-dimethoxybenzylidene-(3-bromo-1-propylamine)

Conditions	Yield
Stage #1: 3-bromopropylamine hydrochloride With triethylamine In chloroform at 20℃; for 0.0833333h; Stage #2: 2,3-dimethyoxybenzaldehyde With magnesium sulfate In chloroform at 20℃; for 16h;	99%

N-(4-aminophenyl)-N'-phenylurea (10141-46-5) + 2,3-dimethyoxybenzaldehyde (86-51-1) → 1-[4-(2,3-dimethoxy-benzylamino)phenyl]-3-phenylurea (1173493-02-1)

Conditions	Yield
With sodium cyanoborohydride In methanol Reflux; Inert atmosphere;	99%

α,α-difluoromethyl p-tolyl sulfoxide (32368-82-4) + 2,3-dimethyoxybenzaldehyde (86-51-1) → 1-(2,3-dimethoxyphenyl)-2,2-difluoro-2-(p-tolylsulfinyl)ethan-1-ol

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -30℃; for 0.666667h; Inert atmosphere; diastereoselective reaction;	99%

malonic acid (141-82-2) + 2,3-dimethyoxybenzaldehyde (86-51-1) → trans-2,3-dimethoxycinnamic acid (7345-82-6)

Conditions	Yield
piperidine In pyridine Heating;	98%
With piperidine; pyridine at 120 - 130℃; Knoevenagel condensation;	89%
Stage #1: malonic acid; 2,3-dimethyoxybenzaldehyde With pyridine at 50℃; Inert atmosphere; Stage #2: With piperidine at 80 - 115℃; for 4h; Inert atmosphere; Stage #3: With hydrogenchloride In water	84%

2,3-dimethyoxybenzaldehyde (86-51-1) → 1,2-dimethoxy-3-methylbenzene (4463-33-6)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol at 20℃; under 760.051 Torr; for 0.75h;	98%
With potassium hydroxide; hydrazine In diethylene glycol at 90 - 100℃; for 1.5h;	81%
With hydrogenchloride; amalgamated zinc; ethanol

benzyloxy-trimethylsilane (14642-79-6) + (2R,3R)-(E)-Methyl 2-acetoxy-3-(dimethylphenylsilyl)-hex-4-enoate (143446-41-7) + 2,3-dimethyoxybenzaldehyde (86-51-1) → (E)-(2S,5S,6R)-Methyl 2-acetoxy-6-(benzyloxy)-6-(2,3-dimethoxyphenyl)-5-methylhex-3-enoate (143446-40-6, 147060-58-0)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 10h;	98%
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 18h;	97%

2,3-dimethyoxybenzaldehyde (86-51-1) → 3-methoxy-2-hydroxybenzaldehyde (148-53-8)

Conditions	Yield
With lithium chloride In N,N-dimethyl-formamide for 22h; Heating;	98%
With aluminum (III) chloride In dichloromethane at -5 - 25℃;	94%
With cerium(III) chloride; sodium iodide In acetonitrile for 7h; dealkylation; Heating;	89%
With magnesium iodide for 10h; neat (no solvent);	80%
With n-butyllithium; lithium 4-methylpiperazin-1-ide In toluene 1.) 15 deg C, 20 min, 2.) 65-70 deg C;	55%

3(5)-amino-1,2,4-triazole (61-82-5) + dimedone (126-81-8) + 2,3-dimethyoxybenzaldehyde (86-51-1) → 9-(2,3-dimethoxyphenyl)-6,6-dimethyl-5,6,7,9-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one

Conditions	Yield
With acetic acid at 60℃; for 0.333333h; Green chemistry;	98%
With nano-AlPO4(SO3H) In acetonitrile at 50℃; for 0.25h;	89%

diethyl 3-(allyloxy)-5-methoxybenzylphosphonate + 2,3-dimethyoxybenzaldehyde (86-51-1) → trans-3-(allyloxy)-2',3',5-trimethoxystilbene

Conditions	Yield
Stage #1: diethyl 3-(allyloxy)-5-methoxybenzylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Horner-Wadsworth-Emmons Olefination; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran at 0℃; Reflux;	98%

5-acetyl-4-methyl-2-phenylthiazole (7520-94-7) + 2,3-dimethyoxybenzaldehyde (86-51-1) → (3E)-(2,3-dimethoxy-phenyl)-1-(4-methyl-2-phenyl-thiazol-5-yl)propenone

Conditions	Yield
With potassium hydroxide In methanol at 20℃; Claisen-Schmidt Condensation;	98%

3-fluoro-1-diethylphosphonomethyl-benzene (63909-57-9) + 2,3-dimethyoxybenzaldehyde (86-51-1) → (E)-1-(3-fluorostyryl)-2,3-dimethoxybenzene

Conditions	Yield
Stage #1: 3-fluoro-1-diethylphosphonomethyl-benzene With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.5h; Horner-Wadsworth-Emmons Olefination; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran at 0 - 20℃; for 20h; Horner-Wadsworth-Emmons Olefination;	98%

2-Hydroxy-1,4-naphthoquinone (83-72-7) + methyl 2-cyanoacetate (105-34-0) + 2,3-dimethyoxybenzaldehyde (86-51-1) → methyl 2-amino-4-(2,3-dimethoxyphenyl)-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromene-3-carboxylate

Conditions	Yield
With ammonium acetate In ethanol; water at 20℃; for 0.116667h; Sonication;	98%

(1S,2S)-trans-2-amino-1-indanol (32151-02-3) + 2,3-dimethyoxybenzaldehyde (86-51-1) → (+)-(1S,2S)-2-(2,3-dimethoxybenzylideneamino)indan-1-ol (94077-04-0)

Conditions	Yield
In benzene for 10h;	97.1%

morpholine (110-91-8) + Sesamol (533-31-3) + 2,3-dimethyoxybenzaldehyde (86-51-1) → 6-((2,3-dimethoxyphenyl)(morpholino)methyl)benzo[d][1,3]dioxol-5-ol (102616-64-8)

Conditions	Yield
In methanol Heating;	97%
In neat (no solvent) at 125℃; for 0.166667h; Solvent; Reagent/catalyst; Microwave irradiation;	87%
In ethanol Reflux;	57%

Methyltriphenylphosphonium bromide (1779-49-3) + 2,3-dimethyoxybenzaldehyde (86-51-1) → 1-ethenyl-2,3-dimethoxybenzene (17055-36-6)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With sodium amide In diethyl ether at 20℃; for 10h; Inert atmosphere; Stage #2: 2,3-dimethyoxybenzaldehyde In diethyl ether at -10 - 20℃; Wittig reaction; Inert atmosphere;	97%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at -30℃; for 1h; Wittig Olefination; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran at -5 - 20℃; Wittig Olefination;	91%
With Amberlite IR-400 In N,N-dimethyl-formamide at 95℃; for 10h; Inert atmosphere;	86%
Stage #1: Methyltriphenylphosphonium bromide With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 3h; Wittig Olefination; Inert atmosphere; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran for 18h; Wittig Olefination; Inert atmosphere; Reflux;	72%
Stage #1: Methyltriphenylphosphonium bromide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Alkaline conditions; Stage #2: 2,3-dimethyoxybenzaldehyde In tetrahydrofuran at 0℃; for 12h; Inert atmosphere;

2-amino-1-tert-butyl-4-cyanopyrrole (269726-49-0) + dimedone (126-81-8) + 2,3-dimethyoxybenzaldehyde (86-51-1) → C26H31N3O3 (1380775-97-2)

Conditions	Yield
With L-proline In ethanol for 6h; Reflux;	97%

3-aminoethyl-2-[(p-trifluoromethoxy)anilino]quinazolin-4(3H)-one (1275601-94-9) + 2,3-dimethyoxybenzaldehyde (86-51-1) → C26H23F3N4O4 (1461736-82-2)

Conditions	Yield
In ethanol at 75℃; for 3h;	97%

Upstream product

• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 91-16-7 1,2-dimethoxybenzene 
• 919112-52-0 2-benzyl-3-(2,3-dimethoxyphenyl)-5-propylcarbamoyl-2,3-dihydroisoxazole-4-carboxylic acid methyl ester 
• 91106-58-0 2-cyano-3t-(2,3-dimethoxy-phenyl)-acrylic acid 
• 56-23-5 tetrachloromethane 
• 7169-06-4 2,3-dimethoxybenzoyl chloride 
• 5653-67-8 2,3-dimethoxybenzyl alcohol 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 74-88-4 methyl iodide 
• 121336-26-3 1,2-Dimethoxy-3-phenethyloxymethyl-benzene 

Downstream Products

• 103387-38-8 1-(2,3-dimethoxy-benzyl)-piperidine 
• 103046-42-0 2,6-bis-(2,3-dimethoxy-trans-styryl)-pyridine 
• 141838-86-0 (E)-2-(2,3-dimethoxystyryl)benzothiazole 
• 110150-61-3 2-(2,3-dimethoxy-trans-styryl)-6-methoxy-quinolin-4-ol 
• 7461-60-1 2,3-dimethoxycinnamic acid 
• 19411-81-5 2-acetyl-3-(2,3-dimethoxy-phenyl)-acrylic acid ethyl ester 
• 42172-50-9 3c-(2,3-dimethoxy-phenyl)-2-phenyl-acrylonitrile 
• 100054-84-0 ethyl-(2,3-dimethoxy-benzyl)-amine 
• 61190-06-5 dimethoxy-2,3 benzylideneaminoacetal diethylique 
• 43087-75-8 3-oxo-1t-(2.3-dimethoxy-phenyl)-buten-⁽¹⁾-oic acid-⁽⁴⁾ 
• 105254-37-3 3t-(2,3-dimethoxy-phenyl)-2-methyl-acrylic acid 
• 6310-60-7 (2,3-dimethoxy-phenyl)-bis-(4-dimethylamino-phenyl)-methane 
• 110662-66-3 N,N'-bis(2,3-dimethoxybenzylidene)-1,2-diaminoethane 
• 152511-59-6 (2,3-dimethoxy-benzyliden)-aniline 

Relevant articles and documents

V2O5@TiO2 Catalyzed Green and Selective Oxidation of Alcohols, Alkylbenzenes and Styrenes to Carbonyls

The versatile application of different functional groups such as alcohols (1° and 2°), alkyl arenes, and (aryl)olefins to construct carbon-oxygen bond via oxidation is an area of intense research. Here, we report a reusable heterogeneous V2O5@TiO2 catalyzed selective oxidation of various functionalities utilizing different mild and eco-compatible oxidants under greener reaction conditions. The method was successfully applied for the alcohol oxidation, oxidative scission of styrenes, and benzylic C?H oxidation to their corresponding aldehydes and ketones. The utilization of mild and eco-friendly oxidizing reagents such as K2S2O8, H2O2 (30 % aq.), TBHP (70 % aq.), broad substrate scope, gram-scale synthesis, and catalyst recyclability are notable features of the developed protocol.

SUBSTITUTED-N-HETEROARYL COMPOUNDS AND USES THEREOF

The present disclosure relates generally to compounds useful for the treatment and/or enhancement of cognitive function and negative symptoms associated with central nervous system disorders where the circuitry involving fast spiking PV+ interneurons and the production of cortical gamma oscillations is disrupted. The subject disclosure enables the manufacture of medicaments as well as compositions containing same for use in methods of therapy and prophylaxis of cognitive dysfunction and negative symptoms.

Method for fully synthesizing berberine

The invention discloses a method for fully synthesizing berberine, and relates to a drug synthesis method. The method realizes the industrial full synthesis production of the berberine and is made from a bulk organic raw material catechol, the raw material is easily available, and the price is low; 2,3-dimethoxybenzaldehyde is obtained through selective formylation and methylation of the catechol;after a piperonyl ring is obtained through a catechol methylenenation reaction, piperonyl amine is synthesized through a one-step catalytic addition reaction, so that the synthesis steps of the piperonyl amine are shortened, the use of toxic cyanide is avoided, and the process is green and sustainable; condensation hydrogenation and salification reactions adopt a 'one-pot method', and thus the time and the energy are saved, and the cost is decreased. Industrialized full synthesis production of the berberine opens up large-scale production of the berberine, meets the clinical and research needs of the berberine in current anti-tumor, anti-blood pressure, anti-heart rhythm, blood sugar reduction, treatment of Alzheimer's disease and the like, provides effective drugs for reducing pain of patients, and has remarkable economic and social benefits.