387-46-2

Basic information

• Product Name: 2,6-Dihydroxybenzaldehyde
• Synonyms: 2,6-DIHYDROXYBENZALDEHYDE;Benzaldehyde, 2,6-dihydroxy-
• CAS NO: 387-46-2
• Molecular Formula: C₇H₆O₃
• Molecular Weight: 138.12
• Product Categories: Aromatic Aldehydes & Derivatives (substituted)
• Mol File: 387-46-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 154-155°C
• Boiling Point: 223°C
• Flash Point: 103°C
• Appearance: /
• Density: 1.409
• Vapor Pressure: 0.065mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.66±0.10(Predicted)
• CAS DataBase Reference: 2,6-Dihydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dihydroxybenzaldehyde(387-46-2)
• EPA Substance Registry System: 2,6-Dihydroxybenzaldehyde(387-46-2)

Safety Data

• Hazardous Substances Data: 387-46-2(Hazardous Substances Data)

Usage

Uses

2,6-Dihydroxybenzaldehyde is a reactant used in the synthesis of cinnamides as potent cholinesterase inhibitors.

InChI:InChI=1/C7H6O3/c8-4-5-6(9)2-1-3-7(5)10/h1-4,9-10H

Synthetic route

2,6-dimethoxybenzaldehyde (3392-97-0) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; for 12h; Green chemistry;	88%
Stage #1: 2,6-dimethoxybenzaldehyde With aluminum (III) chloride In dichloromethane at 20℃; Stage #2: With hydrogenchloride; water In dichloromethane	87%
With aluminum (III) chloride In dichloromethane at 20℃;	78.3%

5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 6h; Inert atmosphere;	82%
With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h;	39%

2,6-bis(1-ethoxyethoxy)benzaldehyde → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
With hydrogenchloride In water at 20℃; for 16h; pH=0.7 - 0.8;	65.6%

5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-benzo[1,3]dioxin-4-one (888958-29-0) → 2,6-dihydroxybenzaldehyde (387-46-2) + 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9)

Conditions	Yield
With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h;	A 35% B 62%

6-methoxysalicylaldehyde (700-44-7) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
With aluminum tri-bromide In benzene for 3h; Ambient temperature;	58%
With aluminium trichloride; benzene

2,6-bis((2-methoxyethoxy)methoxy)benzaldehyde (79834-12-1) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;	47%
With hydrogenchloride In 1,4-dioxane; methanol at 50℃;

2,6-dimethoxybenzaldehyde (3392-97-0) → 6-methoxysalicylaldehyde (700-44-7) + 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0 - 25℃; for 18h; Inert atmosphere;	A 31% B 44%

chloroform (67-66-3) + recorcinol (108-46-3) → 2,6-dihydroxybenzaldehyde (387-46-2) + 2,4-Dihydroxybenzaldehyde (95-01-2)

Conditions	Yield
With sodium hydroxide In water at 60℃; for 8h;	A 40% B 24%

C17H19O5Pol → 2,6-dihydroxybenzaldehyde (387-46-2) + 5-hydroxy-2H-chromene-3-carbaldehyde (1298093-14-7)

Conditions	Yield
With ethanol; pyridinium p-toluenesulfonate In 1,2-dichloro-ethane at 70℃; solid phase reaction;	A 8% B 32%

3-formyl-2, 4-dihydroxybenzoic acid (4435-88-5) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
at 100 - 110℃;

2-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-benzoic acid → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic anhydride; trifluoroacetic acid / 48 h / 20 °C 2: 35 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C View Scheme
Multi-step reaction with 3 steps 1: trifluoroacetic anhydride; trifluoroacetic acid / 48 h / 20 °C 2: 62 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C 3: 39 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C View Scheme

5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-benzo[1,3]dioxin-4-one (888958-29-0) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 62 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C 2: 39 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C View Scheme

2,6-Dihydroxybenzoic acid (303-07-1) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic anhydride; trifluoroacetic acid / 48 h / 20 °C 2: 39 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C View Scheme

1,3-bis(methoxymethyl)resorcinol (57234-29-4) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-BuLi / 17 h / 0 - 20 °C 2: 4 N aq. HCl / methanol; dioxane / 50 °C View Scheme

O-methylresorcine (150-19-6) + (+-)-2-chloro-2-methyl-acetoacetic acid ethyl ester → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 61 percent / PPTS / CH2Cl2 / Ambient temperature 2: 76 percent / BuLi / diethyl ether; hexane / 1.) r.t., 2 h, 2.) r.t., 2 h 3: 98 percent / LiCl / dimethylformamide / 6 h / 75 °C 4: 58 percent / AlBr3 / benzene / 3 h / Ambient temperature View Scheme

1-methoxy-3-tetrahydropyran-2-yloxybenzene (30778-86-0) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent / BuLi / diethyl ether; hexane / 1.) r.t., 2 h, 2.) r.t., 2 h 2: 98 percent / LiCl / dimethylformamide / 6 h / 75 °C 3: 58 percent / AlBr3 / benzene / 3 h / Ambient temperature View Scheme

2-methoxy-6-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde (199388-01-7) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / LiCl / dimethylformamide / 6 h / 75 °C 2: 58 percent / AlBr3 / benzene / 3 h / Ambient temperature View Scheme

4-hydroxysalicylic acid (89-86-1) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminium chloride; diethyl ether / Einleiten von Chlorwasserstoff und Erwaermen des Reaktionsprodukts mit Wasser 2: 100 - 110 °C View Scheme

methyl 2,4-dihydroxybenzoate (2150-47-2) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminium chloride; diethyl ether / Einleiten von Chlorwasserstoff und anschliessendes Erwaermen mit Wasser 2: aq. NaOH solution 3: 100 - 110 °C View Scheme

5-carbomethoxy-6-hydroxysalicylaldehyde (39503-26-9) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH solution 2: 100 - 110 °C View Scheme

7-hydroxy-4-methyl-chromen-2-one (90-33-5, 79566-13-5) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 8 steps 1: potassium carbonate; acetone 2: decalin / Erhitzen auf Siedetemperatur 3: aqueous NaOH 4: aqueous NaOH 5: ethanolic KOH 6: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 7: AlCl3; benzene 8: AlCl3; benzene View Scheme

8-allyl-7-hydroxy-4-methylcoumarin (1616-54-2) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: aqueous NaOH 2: aqueous NaOH 3: ethanolic KOH 4: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 5: AlCl3; benzene 6: AlCl3; benzene View Scheme

7-allyloxy-4-methyl-2H-chromen-2-one (3993-57-5) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 7 steps 1: decalin / Erhitzen auf Siedetemperatur 2: aqueous NaOH 3: aqueous NaOH 4: ethanolic KOH 5: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 6: AlCl3; benzene 7: AlCl3; benzene View Scheme

2-allyl-1,3-dihydroxybenzene (1746-89-0) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: aqueous NaOH 2: ethanolic KOH 3: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 4: AlCl3; benzene 5: AlCl3; benzene View Scheme

1,3-dimethoxy-2-(2-propenyl)benzene (3698-35-9) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: ethanolic KOH 2: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 3: AlCl3; benzene 4: AlCl3; benzene View Scheme

(E)-1,3-dimethoxy-2-(prop-1-en-1-yl)benzene (114568-18-2) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 2: AlCl3; benzene 3: AlCl3; benzene View Scheme

1,3-Dimethoxybenzene (151-10-0) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.83 h / -5 - 20 °C 1.2: 1 h / 0 - 20 °C 2.1: boron tribromide / dichloromethane / 21 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.83 h / Cooling 1.2: 1 h / 0 - 20 °C 2.1: aluminum (III) chloride / dichloromethane / 24 h / 0 - 20 °C View Scheme

recorcinol (108-46-3) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: pyridinium p-toluenesulfonate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; n-heptane / -10 - 0 °C / Inert atmosphere 2.2: -10 - -5 °C 3.1: hydrogenchloride / water / 16 h / 20 °C / pH 0.7 - 0.8 View Scheme

1,3-bis-(1-ethoxy-ethoxy)-benzene (70160-46-2) → 2,6-dihydroxybenzaldehyde (387-46-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; n-heptane / -10 - 0 °C / Inert atmosphere 1.2: -10 - -5 °C 2.1: hydrogenchloride / water / 16 h / 20 °C / pH 0.7 - 0.8 View Scheme

2,6-dihydroxybenzaldehyde (387-46-2) + benzyl bromide (100-39-0) → 3-((3-(benzyloxy)-2-formylphenoxy)methyl)benzene (25983-53-3)

Conditions	Yield
With potassium carbonate In acetonitrile for 2h; Reflux;	97%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;	57%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; Yield given;
With potassium carbonate In dimethyl sulfoxide at 20℃;

isoniazid (54-85-3) + 2,6-dihydroxybenzaldehyde (387-46-2) → 2,6-dihydroxybenzaldehyde isonicotinoyl hydrazone

Conditions	Yield
With acetic acid In ethanol for 24h; Reflux;	97%

2,6-dihydroxybenzaldehyde (387-46-2) + malononitrile (109-77-3) → 3-cyano-5-hydroxy-benzo[b]pyran-2-imine (1205640-45-4)

Conditions	Yield
With potassium hydrogencarbonate at 20℃; for 0.366667h; Knoevenagel condensation; solid phase reaction;	95%

2,6-dihydroxybenzaldehyde (387-46-2) + N-phenylacetoacetamide (102-01-2) + ethyl 2-cyanoacetate (105-56-6) → C20H17N3O4

Conditions	Yield
With ammonium acetate In ethanol at 20℃; for 0.25h; Green chemistry;	93%

Diethyl phosphonate (762-04-9, 123-22-8) + 2,6-dihydroxybenzaldehyde (387-46-2) + aniline (62-53-3) → C17H22NO5P

Conditions	Yield
bismuth (III) nitrate pentahydrate for 0.0333333h; microwave irradiation;	92%

2,6-dihydroxybenzaldehyde (387-46-2) + p-toluic hydrazide (3619-22-5) → 2,6-dihydroxybenzaldehyde 4-methylbenzohydrazone

Conditions	Yield
With acetic acid In ethanol for 2h; Reflux;	92%

2,6-dihydroxybenzaldehyde (387-46-2) + 4-chlorobenzoic acid hydrazide (536-40-3) → 2,6-dihydroxybenzaldehyde 4-chlorobenzohydrazone

Conditions	Yield
With acetic acid In ethanol for 24h; Reflux;	92%

2,6-dihydroxybenzaldehyde (387-46-2) + 6-Bromo-1-hexene (2695-47-8) → 2,6-bis(hex-5-en-1-yloxy)benzaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	92%

2,6-dihydroxybenzaldehyde (387-46-2) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → 5-hydroxycoumarin (6093-67-0)

Conditions	Yield
Stage #1: 2,6-dihydroxybenzaldehyde; ethyl (triphenylphosphoranylidene)acetate at 20℃; for 2h; Wittig olefination; Stage #2: Reflux;	90%
With N,N-diethylaniline for 0.333333h; Heating;	81%

4-bromoethylbutanoate (2969-81-5) + 2,6-dihydroxybenzaldehyde (387-46-2) → 4-[3-(3-Ethoxycarbonyl-propoxy)-2-formyl-phenoxy]-butyric acid ethyl ester (197589-71-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; Inert atmosphere;	90%
With potassium carbonate at 60 - 80℃; for 5h; Williamson ether synthesis;	83%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;	65%

cycl-isopropylidene malonate (2033-24-1) + 2,6-dihydroxybenzaldehyde (387-46-2) → 5-hydroxycoumarin-3-carboxylic acid (90947-66-3)

Conditions	Yield
With [Hmim]Tfa for 0.75h;	90%
With ziconium(IV) oxychloride octahydrate for 0.1h; Neat (no solvent); Sonication;	84%

2,6-dihydroxybenzaldehyde (387-46-2) + C14H18Br4O3 → C35H40Br6O9

Conditions	Yield
With potassium carbonate In N,N-dimethyl-d6-formamide at 100℃; for 48h; Inert atmosphere;	89%

2,6-dihydroxybenzaldehyde (387-46-2) + 3-phenyl-propenal (104-55-2) → 3-benzyl-5-hydroxy-2H-1-benzopyran-2-one (1439930-28-5)

Conditions	Yield
With potassium carbonate; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 110℃; for 0.833333h; Inert atmosphere; Microwave irradiation;	88%

2,6-dihydroxybenzaldehyde (387-46-2) + 3-(Chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-1-ium chloride (1446321-95-4) → 2-hydroxy-6-([2-[1-(propan-2-yl)-1H-pyrazol-5-yl]pyridin-3-yl]methoxy)benzaldehyde (1446321-46-5)

Conditions	Yield
Stage #1: 2,6-dihydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride In N,N-dimethyl-formamide at 20 - 50℃; for 2h; Inert atmosphere;	88%
Stage #1: 2,6-dihydroxybenzaldehyde With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	37%

2,6-dihydroxybenzaldehyde (387-46-2) + 2-(3,5-dihydroxyphenyl)acetic acid (4670-09-1) → 5-hydroxy-3-(3,5-dihydroxyphenyl)coumarin

Conditions	Yield
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	86%

2,6-dihydroxybenzaldehyde (387-46-2) → 2,6-bis(trifluoromethanesulfonyloxy)benzaldehyde

Conditions	Yield
With trifluoromethylsulfonic anhydride In pyridine; dichloromethane at 0 - 20℃; for 3h;	85%

2,6-dihydroxybenzaldehyde (387-46-2) + C18H26Br4O3 → C43H56Br6O9

Conditions	Yield
With potassium carbonate In N,N-dimethyl-d6-formamide at 100℃; for 48h; Inert atmosphere;	85%

2,6-dihydroxybenzaldehyde (387-46-2) + p-benzoquinone (106-51-4) → 1,4,8-trihydroxy-9H-xanthen-9-one (1216863-88-5)

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate In 1,2-dichloro-ethane at 90℃; for 16h;	84%

4-bromo-trans-crotonic acid ethyl ester (37746-78-4) + 2,6-dihydroxybenzaldehyde (387-46-2) → C13H14O5 (1130247-26-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	82%

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) + 2,6-dihydroxybenzaldehyde (387-46-2) → 5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (148356-24-5)

Conditions	Yield
Stage #1: 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone With thiamine hydrochloride In ethanol at 20℃; for 0.25h; Green chemistry; Stage #2: 2,6-dihydroxybenzaldehyde In ethanol at 20℃; for 1.5h; Green chemistry;	82%

2,6-dihydroxybenzaldehyde (387-46-2) + malononitrile (109-77-3) → 5-hydroxy-2-oxo-2H-chromene-3-carbonitrile (1158276-04-0)

Conditions	Yield
With zirconium(IV) chloride; 1-butyl-3-methylimidazolium Tetrafluoroborate at 25℃; for 0.583333h; Knoevenagel condensation;	81%

Nicotinic acid hydrazide (553-53-7) + 2,6-dihydroxybenzaldehyde (387-46-2) → 2,6-dihydroxybenzaldehyde nicotinoyl hydrazone

Conditions	Yield
With acetic acid In ethanol for 6h; Reflux;	81%

2-[{5-phenyl-[1,3,4]-thiadiazol-2-yl}imino]-1,3-thiazolidin-4-one (89335-17-1) + 2,6-dihydroxybenzaldehyde (387-46-2) → C18H12N4O3S2

Conditions	Yield
With sodium acetate; acetic acid In acetic anhydride at 2 - 105℃; for 12h; Temperature; Knoevenagel Condensation;	80.25%

2,6-dihydroxybenzaldehyde (387-46-2) + 2-Bromo-4'-methoxyacetophenone (2632-13-5) → 5-hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one

Conditions	Yield
Stage #1: 2-Bromo-4'-methoxyacetophenone With thiamine hydrochloride In ethanol at 20℃; for 0.25h; Green chemistry; Stage #2: 2,6-dihydroxybenzaldehyde In ethanol at 20℃; for 1.58333h; Green chemistry;	80%

2,6-dihydroxybenzaldehyde (387-46-2) + chloromethyl methyl ether (107-30-2) → 2,6-bis((2-methoxyethoxy)methoxy)benzaldehyde (79834-12-1)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	79%
With potassium carbonate In acetone at 0 - 20℃; for 0.75h;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2,6-dihydroxybenzaldehyde (387-46-2) → C13H4Cl4N6O3 (1408326-41-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃;	78%

2,6-dihydroxybenzaldehyde (387-46-2) + cyclohexanecarbohydrazide (38941-47-8) → 2,6-dihydroxybenzaldehyde cyclohexanecarbohydrazone

Conditions	Yield
With acetic acid In ethanol for 7h; Reflux;	77%

2,6-dihydroxybenzaldehyde (387-46-2) + 3-chlorobenzhydrazide (1673-47-8) → 2,6-dihydroxybenzaldehyde 3-chlorobenzohydrazone

Conditions	Yield
With acetic acid In ethanol for 4h; Reflux;	76%

Upstream product

• 700-44-7 6-methoxysalicylaldehyde 
• 79834-12-1 2,6-bis((2-methoxyethoxy)methoxy)benzaldehyde 
• 154714-19-9 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 70160-46-2 1,3-bis-(1-ethoxy-ethoxy)-benzene 
• 108-46-3 recorcinol 
• 3392-97-0 2,6-dimethoxybenzaldehyde 
• 151-10-0 1,3-Dimethoxybenzene 
• 3698-35-9 1,3-dimethoxy-2-(2-propenyl)benzene 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 39503-26-9 5-carbomethoxy-6-hydroxysalicylaldehyde 
• 2150-47-2 methyl 2,4-dihydroxybenzoate 
• 89-86-1 4-hydroxysalicylic acid 
• 30778-86-0 1-methoxy-3-tetrahydropyran-2-yloxybenzene 
• 150-19-6 O-methylresorcine 

Downstream Products

• 860540-64-3 (2-formyl-3-hydroxy-phenoxy)-acetic acid 
• 700-44-7 6-methoxysalicylaldehyde 
• 3392-97-0 2,6-dimethoxybenzaldehyde 
• 856357-88-5 (2-formyl-3-hydroxy-phenoxy)-acetic acid ethyl ester 
• 127724-14-5 ethyl 4-hydroxybenzofuran-2-carboxylate 
• 1229183-62-3 C₂₃H₂₈N₂O₇ 
• 1229183-63-4 C₂₄H₃₀N₂O₇ 
• 1229183-64-5 C₂₅H₃₂N₂O₇ 
• 1229183-61-2 C₂₂H₂₆N₂O₇ 
• 1298093-39-6 2-hydroxy-6-[(tetrahydro-2H-pyran-2-yl)oxy]benzaldehyde 
• 1408326-59-9 C₃₂H₄₂N₈O₆ 
• 1408326-61-3 C₃₁H₃₈N₈O₅ 
• 1408326-63-5 C₃₁H₄₀N₈O₆ 
• 1408326-41-9 C₁₃H₄Cl₄N₆O₃ 

Relevant articles and documents

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Disclosed herein are processes for synthesizing 2-hydroxy-6-((2-(1-isopropyl-1H- pyrazol-5-yl)-pyridin-3-yl)methoxy)benzaldehyde (also referred to herein as Compound (I)) and intermediates used in such processes. Compound (I) binds to hemoglobin and increases it oxygen affinity and hence can be useful for the treatment of diseases such as sickle cell disease.

Discovery and Rational Design of Natural-Product-Derived 2-Phenyl-3,4-dihydro-2H-benzo[f]chromen-3-amine Analogs as Novel and Potent Dipeptidyl Peptidase 4 (DPP-4) Inhibitors for the Treatment of Type 2 Diabetes

Starting from the lead isodaphnetin, a natural product inhibitor of DPP-4 discovered through a target fishing docking based approach, a series of novel 2-phenyl-3,4-dihydro-2H-benzo[f]chromen-3-amine derivatives as potent DPP-4 inhibitors are rationally designed utilizing highly efficient 3D molecular similarity based scaffold hopping as well as electrostatic complementary methods. Those ingenious drug design strategies bring us approximate 7400-fold boost in potency. Compounds 22a and 24a are the most potent ones (IC50 ≈ 2.0 nM) with good pharmacokinetic profiles. Compound 22a demonstrated stable pharmacological effect. A 3 mg/kg oral dose provided >80% inhibition of DPP-4 activity within 24 h, which is comparable to the performance of the long-acting control omarigliptin. Moreover, the efficacy of 22a in improving the glucose tolerance is also comparable with omarigliptin. In this study, not only promising DPP-4 inhibitors as long acting antidiabetic that are clinically on demand are identified, but the target fish docking and medicinal chemistry strategies were successfully implemented.