22608-87-3

Basic information

• Product Name: 2-Amino-4,5-dimethoxy-benzaldehyde
• Synonyms: 2-Amino-4,5-dimethoxy-benzaldehyde;Benzaldehyde, 2-amino-4,5-dimethoxy-;2-AMino-4,5-diMethyloxybenzaldehyde
• CAS NO: 22608-87-3
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181
• Mol File: 22608-87-3.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 348 °C at 760 mmHg
• Flash Point: 189.7 °C
• Appearance: /
• Density: 1.196 g/cm³
• Vapor Pressure: 5.18E-05mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2-Amino-4,5-dimethoxy-benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4,5-dimethoxy-benzaldehyde(22608-87-3)
• EPA Substance Registry System: 2-Amino-4,5-dimethoxy-benzaldehyde(22608-87-3)

Safety Data

• Hazardous Substances Data: 22608-87-3(Hazardous Substances Data)

Usage

General Description

2-Amino-4,5-dimethoxy-benzaldehyde, also known as DMAB, is a chemical compound with a benzaldehyde core substituted with amino and dimethoxy functional groups. It is commonly used as a precursor in the synthesis of various pharmaceuticals and organic compounds. DMAB is also utilized in the preparation of heterocyclic compounds and as a reagent in organic chemistry reactions. Its unique structure and properties make it a valuable component in chemical research and development, particularly in the pharmaceutical and biotechnology industries.

InChI:InChI=1/C9H11NO3/c1-12-8-3-6(5-11)7(10)4-9(8)13-2/h3-5H,10H2,1-2H3

Synthetic route

2-nitroveratraldehyde (20357-25-9) → 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3)

Conditions	Yield
With iron; ammonium chloride In water; ethyl acetate at 20℃; for 120h;	100%
With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran at 20℃; under 2585.81 Torr; for 0.25h;	99%
With palladium on activated charcoal; hydrogen at 20℃; for 0.0833333h;	99%

N-(6,7-dimethoxy-2-methylquinazolin-3-io)-N-amide (74990-23-1) → O-Ethyl N-Butylthiocarbamate (55365-85-0) + 2-acetylamino-4,5-dimethoxybenzaldehyde (22608-86-2) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) + 2-amino-4,5-dimethoxybenzaldehyde hydrazone

Conditions	Yield
In various solvent(s) for 3h; Ambient temperature; Irradiation;	A 11% B 1% C 22.5% D 29.5%
In various solvent(s) for 3h; Ambient temperature;	A 11% B 1% C 22.5% D 29.5%

(2-amino-4,5-dimethoxy-benzyliden)-aniline → 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3)

Conditions	Yield
With alkaline solution

ammonia (7664-41-7) + 2-nitroveratraldehyde (20357-25-9) + aqueous FeSO4 → 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3)

methanol (67-56-1) + 2-nitroveratraldehyde (20357-25-9) + palladium/charcoal → 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3)

Conditions	Yield
Hydrogenation;

(3,4-dimethoxy-6-nitro-benzyliden)-aniline (63190-11-4) → 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium sulfide; alcohol 2: diluted alkaline solution View Scheme

2-Amino-4,5-dimethoxybenzoic acid (5653-40-7) → 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / -10 - 20 °C / Inert atmosphere 2: manganese(IV) oxide / dichloromethane / 20 °C View Scheme
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere 2: manganese(IV) oxide / dichloromethane / Inert atmosphere View Scheme

(2-amino-4,5-dimethoxyphenyl)methanol (188174-23-4) → 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3)

Conditions	Yield
With manganese(IV) oxide In dichloromethane at 20℃;
With manganese(IV) oxide In dichloromethane Inert atmosphere;

3,4-dimethoxy-benzaldehyde (120-14-9) → 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / water 2: hydrogenchloride; iron / ethanol View Scheme
Multi-step reaction with 2 steps 1: nitric acid / 2 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: nitric acid / 2 h / 0 - 20 °C 2: iron; ammonium chloride / ethyl acetate; water / 120 h / 20 °C View Scheme

2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) + trifluoroacetic anhydride (407-25-0) → 2,2,2-trifluoro-N-(2-formyl-4,5-dimethoxyphenyl)acetamide (1309581-09-6)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	98%

2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) + p-toluenesulfonyl chloride (98-59-9) → N-(2-formyl-4,5-dimethoxyphenyl)-4-methylbenzenesulfonamide (886499-20-3)

Conditions	Yield
With pyridine In chloroform at 20℃; for 10h;	97%

3-acetyltropolone (72023-82-6) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 3-(6,7-dimethoxyquinol-2-yl)tropolone

Conditions	Yield
With sodium ethanolate In ethanol for 4h; Heating;	96%

1-Methyl-4-piperidone (1445-73-4) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 7,8-dimethoxy-2-methyl-1,2,3,4-tetrahydro-benzo[b][1,6]naphthyridine (1114775-84-6)

Conditions	Yield
With sodium ethanolate In ethanol for 2h; Friedlaender reaction; Heating;	95%

2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) + 3-Acetyl-5-methyltropolone (125312-75-6) → 5-methyl-3-(6,7-dimethoxyquinol-2-yl)tropolone

Conditions	Yield
With sodium ethanolate In ethanol for 4h; Heating;	94%

maleic anhydride (108-31-6) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → (Z)-3-(2-Formyl-4,5-dimethoxy-phenylcarbamoyl)-acrylic acid

Conditions	Yield
In diethyl ether for 0.333333h; Ambient temperature;	90%

Tetrahydro-4H-pyran-4-one (29943-42-8) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 7,8-dimethoxy-3,4-dihydro-1H-pyrano[4,3-b]quinoline (1114775-90-4)

Conditions	Yield
With sodium ethanolate In ethanol for 1.5h; Friedlaender reaction; Heating;	90%

Tetrahydrothiopyran-4-one (1072-72-6) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 6,7-dimethoxy-3,4-dihydro-1H-2-thia-10-aza-anthracene (1114775-88-0)

Conditions	Yield
With sodium ethanolate In ethanol Friedlaender reaction; Heating;	90%

2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) + N-ethoxycarbonyl-4-piperidone (29976-53-2) → 7,8-dimethoxy-3,4-dihydro-1H-benzo[b][1,6]naphthyridine-2-carboxylic acid ethyl ester (1114775-82-4)

Conditions	Yield
With sodium ethanolate In ethanol for 2h; Friedlaender reaction; Heating;	90%

1-(4-nitrophenoxy)propan-2-one (6698-72-2) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 6,7-dimethoxy-2-methyl-3-(4-nitrophenoxy)quinoline (1452849-32-9)

Conditions	Yield
With piperidine In ethanol for 24h; Reflux;	90%
With piperidine In ethanol for 24h; Friedlaender Quinoline Synthesis; Reflux;	85%

3,5-dimethyl-4-nitroisoxazole (1123-49-5) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → C14H17N3O6

Conditions	Yield
With triethylammonium acetate In neat (no solvent) at 60℃; for 0.583333h;	89%

N-[2-(1H-indol-3-yl)ethyl]-2-cyano acetamide (103344-22-5) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → C22H22N4O3 (1373889-59-8)

Conditions	Yield
With sodium hydroxide In ethanol at 70℃; Friedlaender synthesis;	87%

2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) + 1-phenyl-propan-1-one (93-55-0) → (6,7-dimethoxyquinolin-3-yl)(phenyl)methanone (107572-53-2)

Conditions	Yield
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In toluene at 120℃; for 14h; Inert atmosphere; Sealed tube;	86%

3,4-dihydro-6,7-dimethoxyisoquinoline hydrochloride (20232-39-7) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 2,3,10,11-tetramethoxy-5,6,13,13a-tetrahydroisoquino<1,2-b>quinazolinium chloride (114688-70-9)

Conditions	Yield
In ethanol for 1h; Heating;	85%
In ethanol for 1h; Heating;

2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) + 6-methoxy-3,4-dihydroisoquinoline hydrochloride (93549-15-6) → 3,10,11-trimethoxy-5,6,13,13a-tetrahydroisoquino<1,2-b>quinazolinium chloride

Conditions	Yield
In ethanol for 1h; Heating;	84%

2-acetylazulene (54899-82-0) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 2-Azulen-2-yl-6,7-dimethoxy-quinoline

Conditions	Yield
With sodium ethanolate In ethanol for 6h; Heating;	83%

neopentyl chloride (753-89-9) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 2-(2,2-dimethylpropionylamino)-4,5-dimethoxybenzaldehyde

Conditions	Yield
In pyridine; benzene for 24h; Ambient temperature;	82%

3,4-dihydroisoquinolinium picrate (63994-91-2) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 10,11-dimethoxy-5,6,13,13a-tetrahydroisoquino<1,2-b>quinazolinium picrate (114688-75-4)

Conditions	Yield
In ethanol for 1h; Heating;	82%

2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) + Propargylamine (2450-71-7) → 6,7-dimethoxy-2-methylquinolin-3-amine (861036-58-0)

Conditions	Yield
With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In acetonitrile at 50℃; for 20h; Inert atmosphere;	80%

2-(pyrid-3-yl)acetaldehyde (42545-63-1) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 6,7-dimethoxy-3-pyridin-3-ylquinoline

Conditions	Yield
With sodium hydroxide In ethanol for 0.333333h; Heating;	79%

ethyl Bromopyruvate (70-23-5) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → ethyl 3-amino-6,7-dimethoxy-2-quinolinecarboxylate (690253-80-6)

Conditions	Yield
Stage #1: ethyl Bromopyruvate With pyridine In ethanol at 60 - 70℃; for 1h; Stage #2: 2-amino-4,5-dimethoxybenzaldehyde With pyridine In ethanol for 5h; Heating; Stage #3: With pyrrolidine In ethanol for 2h; Heating; Further stages.;	79%

phenylacetaldehyde (122-78-1) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 3-phenyl-6,7-dimethoxy-quinoline (146535-52-6)

Conditions	Yield
With ytterbium(III) triflate In toluene for 5h; Friedlaender reaction; Heating;	78.4%
With sodium hydroxide In ethanol for 0.333333h; Heating;	61%

p-cyanocinnamaldehyde (41917-85-5) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → C19H16O3N2

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In N,N-dimethyl-formamide at -25℃; for 48h; aza-Michael-aldol reaction;	78%
With benzoic acid; pyrrolidine In dimethyl sulfoxide at 20℃; for 3h; aza-Michael aldol condensation;	56%

n-octyne (629-05-0) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 2-hexyl-6,7-dimethoxyquinoline (1248332-56-0)

Conditions	Yield
With pyrrolidine; copper(l) iodide In acetonitrile at 100℃; for 12h; Inert atmosphere;	78%

2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) + benzoyl chloride (98-88-4) → N-(2-formyl-4,5-dimethoxyphenyl)benzamide

Conditions	Yield
With triethylamine In dichloromethane Cooling with ice;	78%

C15H14N2O (1373889-90-7) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → C24H23N3O3 (1373889-61-2)

Conditions	Yield
With sodium hydroxide In ethanol at 70℃; Friedlaender synthesis;	76%

2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) + 2-(thiophen-3-yl)acetaldehyde (114633-95-3) → RPR 101511

Conditions	Yield
With sodium hydroxide In ethanol for 0.333333h; Heating;	75%

N-phenacylpyridinium bromide (16883-69-5) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 6,7-dimethoxy-2-phenyl-quinolin-3-ylamine

Conditions	Yield
Stage #1: N-phenacylpyridinium bromide; 2-amino-4,5-dimethoxybenzaldehyde With pyridine; dmap In ethanol for 48h; Heating; Stage #2: With pyrrolidine In ethanol Heating; Further stages.;	75%

5-Bromo-1-indanone (34598-49-7) + 2-amino-4,5-dimethoxybenzaldehyde (22608-87-3) → 2-bromo-7,8-dimethoxy-11H-indeno[1,2-b]quinoline

Conditions	Yield
With sodium ethanolate In ethanol for 2h; Friedlaender condensation; Heating;	75%

Upstream product

• 63190-11-4 (3,4-dimethoxy-6-nitro-benzyliden)-aniline 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 188174-23-4 (2-amino-4,5-dimethoxyphenyl)methanol 
• 5653-40-7 2-Amino-4,5-dimethoxybenzoic acid 
• 67-56-1 methanol 
• 20357-25-9 6-nitroveratraldehyde 
• 7664-41-7 ammonia 
• 74990-23-1 N-(6,7-dimethoxy-2-methylquinazolin-3-io)-N-amide 

Downstream Products

• 23046-03-9 5,6-dimethoxy-benzo[b]thiophene-2-carboxylic acid 
• 876479-46-8 (3,4-dimethoxy-phenyl)-acetic acid-(2-formyl-4,5-dimethoxy-anilide) 
• 57179-07-4 6,7-dimethoxy-2-phenylquinoline 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 18093-05-5 6-chloroverataldehyde 
• 14382-91-3 2-hydroxy-4,5-dimethoxybenzaldehyde 
• 61203-53-0 2-iodo-4,5-dimethoxybenzaldehyde 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 
• 1114775-86-8 (7,8-dimethoxy-3,4-dihydro-1H-benzo[b][1,6]naphthyridin-2-yl)-phenyl-methanone 
• 114688-60-7 2-(2-amino-4,5-dimethoxybenzyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline 

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