3328-69-6

Basic information

• Product Name: 2,6-DIFORMYLPHENOL
• Synonyms: 2-HYDROXYISOPHTHALALDEHYDE;2,6-DIFORMYLPHENOL
• CAS NO: 3328-69-6
• Molecular Formula: C₈H₆O₃
• Molecular Weight: 150.13
• Mol File: 3328-69-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 124 °C
• Boiling Point: 219°C at 760 mmHg
• Flash Point: 100.5°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 0.0827mmHg at 25°C
• Refractive Index: 1.672
• Storage Temp.: Refrigerator
• Solubility: soluble in Methanol
• PKA: 6.38±0.10(Predicted)
• CAS DataBase Reference: 2,6-DIFORMYLPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIFORMYLPHENOL(3328-69-6)
• EPA Substance Registry System: 2,6-DIFORMYLPHENOL(3328-69-6)

Safety Data

• Hazardous Substances Data: 3328-69-6(Hazardous Substances Data)

Usage

General Description

2,6-DIFORMYLPHENOL is a chemical compound with the molecular formula C8H6O3. It is a white to yellow crystalline powder that is used as a chemical intermediate in the production of pharmaceuticals, dyes, and other organic compounds. It is also utilized in the synthesis of advanced polymers and resins. 2,6-DIFORMYLPHENOL is considered to be a potentially hazardous substance and should be handled with caution. It has a variety of industrial applications and is commonly used in the manufacturing of plastics and pharmaceuticals.

InChI:InChI=1/C8H6O3/c9-4-6-2-1-3-7(5-10)8(6)11/h1-5,11H

Synthetic route

Cu2(C6H3(O)(CHNCH2CH2C5H4N)2)OH(2+)*2BF4(1-)=[Cu2(C6H3(O)(CHNCH2CH2C5H4N)2)OH](BF4)2 → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
With hydrogenchloride; water Hydrolysis of Cu-complex, using aq. HCl.;	80%

2,6-(α,α,α',α'-tetrabromo)dimethylacetoxybenzene (176243-28-0) → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
With sodium acetate In acetic acid for 48h; Heating;	72%
With potassium hydroxide for 3h; Heating;	67%

hexamethylenetetramine (100-97-0) + phenol (108-95-2) → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
In trifluoroacetic acid for 6h; Reflux;	65.1%
With trifluoroacetic acid at 24℃; Inert atmosphere; Reflux;

trifluoroacetic acid (76-05-1) + phenol (108-95-2) → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
With hexamethylenetetramine Reflux;	65.1%
With hexamethylenetetramine Reflux;	65.1%
With hexamethylenetetramine Reflux;	65.1%

2,6-dimethylphenyl acetate (876-98-2) → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
Stage #1: 2,6-dimethylphenyl acetate With chromium(VI) oxide; sulfuric acid; acetic anhydride; acetic acid at 0℃; for 20h; Stage #2: With sulfuric acid In ethanol for 1h; Reflux;	30%
Multi-step reaction with 2 steps 1: 88 percent / N-bromosuccinimide / CCl4 / 10 h / Heating; Irradiation 2: 72 percent / sodium acetate / acetic acid / 48 h / Heating View Scheme

cyclohexenone (930-68-7) + formic acid ethyl ester (109-94-4) → 2-hydroxy-isophthalaldehyde (3328-69-6) + 6-[1-Hydroxy-meth-(Z)-ylidene]-cyclohex-2-enone (15329-04-1)

Conditions	Yield
With methanol; sodium hydride In tetrahydrofuran 1.) 0 deg C; 2.) 2 h RT;	A 10% B 25%

chloroform (67-66-3) + phenol (108-95-2) → 2-hydroxy-isophthalaldehyde (3328-69-6) + 5-formyl-2-hydroxybenzaldehyde (3328-70-9) + 4-hydroxy-benzaldehyde (123-08-0) + salicylaldehyde (90-02-8)

Conditions	Yield
With methanol; sodium hydroxide In water for 1h; Heating;	A 3% B 4% C 11% D 15%

hexamethylenetetramine (100-97-0) + salicylaldehyde (90-02-8) → 2-hydroxy-isophthalaldehyde (3328-69-6) + 5-formyl-2-hydroxybenzaldehyde (3328-70-9)

Conditions	Yield
Stage #1: hexamethylenetetramine; salicylaldehyde With copper(I) oxide In trifluoroacetic acid for 5h; Duff Aldehyde Synthesis; Reflux; Stage #2: With hydrogenchloride In water at 20℃; for 1h; regioselective reaction;	A 10.5% B 9.5%

3-formylsalicylic acid (610-04-8) → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
With hydrogenchloride; sodium amalgam; boric acid; sodium hydrogensulfite Ausbeute ca.20prozent;

Isophthalaldehyde (626-19-7) → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
With hydrogenchloride; Cu(MeCN)ClO4; oxygen; (S)-methyl 2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoate 1.) methanol, reflux, 2.) methanol; Multistep reaction;
Multi-step reaction with 3 steps 1: methanol 2: O2 / acetonitrile 3: H2SO4 / sulfuric acid View Scheme

chloroform (67-66-3) + salicylaldehyde (90-02-8) → 2-hydroxy-isophthalaldehyde (3328-69-6) + 4-oxy-isophthalaldehyde

Conditions	Yield
With sodium hydroxide

2.6-dimethylphenol (576-26-1) + 1-trans-cinnamoyl-pyridinium chloride → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: NEt3 / CH2Cl2 2: 88 percent / N-bromosuccinimide / CCl4 / 10 h / Heating; Irradiation 3: 72 percent / sodium acetate / acetic acid / 48 h / Heating View Scheme

2,6-dimethylphenyl acetate (876-98-2) → 2-hydroxy-isophthalaldehyde (3328-69-6) + potassium hydroxide

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / Br2 / CCl4 / 12 h / Heating; Irradiation 2: 67 percent / aq. KOH / 3 h / Heating View Scheme

{Cu2(mbO-L-Mehis)(OH)}{ClO4}2 → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
With H2SO4 In sulfuric acid aq. H2SO4; treating sample with dild. H2SO4; extg. with ether or chloroform;

{Cu2(mbO-Mehim)(OH)}{ClO4}2 → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
With H2SO4 In sulfuric acid aq. H2SO4; treating sample with dild. H2SO4; extg. with ether or chloroform;

{Cu2(mb-Mehim)}{ClO4}2 → 2-hydroxy-isophthalaldehyde (3328-69-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: O2 / acetonitrile 2: H2SO4 / sulfuric acid View Scheme

2-(aminoethyl)pyridine (2706-56-1) + 2-hydroxy-isophthalaldehyde (3328-69-6) → 2,6-bis-1-hydroxybenzene (115010-23-6)

Conditions	Yield
In methanol for 1h; Heating;	100%
In dichloromethane for 1h;

2-hydroxy-isophthalaldehyde (3328-69-6) + naphthalene-1,8-diamine (479-27-6) → 2,6-bis(2,3-dihydro-1H-perimidin-2-yl)phenol (1252687-55-0)

Conditions	Yield
With zinc(II) acetate dihydrate In methanol at 20℃; for 18h;	94%

2-hydroxy-isophthalaldehyde (3328-69-6) → dimethyl 2-hydroxyisophthalate (36669-06-4)

Conditions	Yield
With sodium hydroxide; silver(l) oxide In water at 60℃; for 0.166667h;	93%

2-hydroxy-isophthalaldehyde (3328-69-6) → 2‑hydroxy‑5‑nitroisophthalaldehyde (137605-43-7)

Conditions	Yield
With nitric acid In acetic acid Nitration; Heating;	90%

2-hydroxy-isophthalaldehyde (3328-69-6) + 6-Bromo-1-hexene (2695-47-8) → 4-(tert-butyl)-2,6-di(hept-6-en-1-yl)phenol

Conditions	Yield
Stage #1: 6-Bromo-1-hexene With magnesium In tetrahydrofuran for 3h; Reflux; Stage #2: 2-hydroxy-isophthalaldehyde In tetrahydrofuran at 0℃; Inert atmosphere; Reflux; Stage #3: With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at -78℃; for 1h; Inert atmosphere;	84%

n-Butyl chloride (109-69-3) + 2-hydroxy-isophthalaldehyde (3328-69-6) → 2-butoxyisophthalaldehyde (1422257-46-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h;	81%

1,4-dibromo-butane (110-52-1) + 2-hydroxy-isophthalaldehyde (3328-69-6) → 1,4-di(2,6-diformylphenoxy)butane

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 2h;	78%

2-hydroxy-isophthalaldehyde (3328-69-6) → 2,6-bis(hydroxymethyl)phenol (2937-59-9)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 2h;	77%
With lithium aluminium tetrahydride In diethyl ether for 4h; Inert atmosphere;

2-hydroxy-isophthalaldehyde (3328-69-6) + C17H18N(1+) → C42H41N2O(1+)

Conditions	Yield
In toluene; butan-1-ol for 3h; Reflux;	76%

2-hydroxy-isophthalaldehyde (3328-69-6) + 2-amino-benzenethiol (137-07-5) → 3-(benzo[d]thiazol-2-yl)-2-hydroxybenzaldehyde

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide In ethanol; water at 20℃; for 0.5h;	68.2%
With hydrogenchloride; dihydrogen peroxide In ethanol; water at 20℃; for 0.5h;	68.2%
With hydrogenchloride; dihydrogen peroxide In ethanol; water at 20℃; for 0.5h;	68.2%
With hydrogenchloride; dihydrogen peroxide In ethanol; water at 20℃; for 0.5h;	68.2%

2-hydroxy-isophthalaldehyde (3328-69-6) + 2,6-diisopropylbenzenamine (24544-04-5) → 2,6-bis(((2,6-diisopropylphenyl)imino)methyl)phenol

Conditions	Yield
With formic acid In methanol at 20℃; for 3h; Glovebox; Inert atmosphere;	61%

1,2-bis-(2-bromo-ethoxy)-ethane (31255-10-4) + 2-hydroxy-isophthalaldehyde (3328-69-6) → 1,8-bis(2,6-diformylphenoxy)-3,6-dioxaoctane (849587-67-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 24h;	51%

2-hydroxy-isophthalaldehyde (3328-69-6) + 3,6,15-triamino-1,8,13-trihexyloxytriptycene → C200H224N12O18

Conditions	Yield
With trifluoroacetic acid In tetrahydrofuran at 20℃; for 96h; Sealed tube; Inert atmosphere;	50%

4,4''-diamino-3,3'',5,5''-tetraisopropyl-o-terpenyl hydrochloride + 2-hydroxy-isophthalaldehyde (3328-69-6) → C76H84N4O2

Conditions	Yield
In ethanol at 70℃; for 72h;	47%

2-hydroxy-isophthalaldehyde (3328-69-6) → C24H24O6 (204781-88-4)

Conditions	Yield
With triethylsilane; trimethylsilyl trifluoromethanesulfonate at -78℃; for 8h;	14%

2-hydroxy-isophthalaldehyde (3328-69-6) + 1-[(2S)-N-Benzylpyrrolidin-2-yl]methanamine (96948-23-1) → 2,6-Bis-{[(E)-(S)-1-benzyl-pyrrolidin-2-ylmethylimino]-methyl}-phenol

Conditions	Yield
In methanol for 1h; Ambient temperature;

Upstream product

• 610-04-8 3-formylsalicylic acid 
• 76-05-1 trifluoroacetic acid 
• 108-95-2 phenol 
• 100-97-0 hexamethylenetetramine 
• 90-02-8 salicylaldehyde 
• 876-98-2 2,6-dimethylphenyl acetate 
• 576-26-1 2.6-dimethylphenol 
• 67-66-3 chloroform 
• 176243-28-0 2,6-(α,α,α',α'-tetrabromo)dimethylacetoxybenzene 
• 930-68-7 cyclohexenone 
• 109-94-4 formic acid ethyl ester 
• 626-19-7 Isophthalaldehyde 

Downstream Products

• 115010-23-6 2,6-bis-1-hydroxybenzene 
• 36669-06-4 dimethyl 2-hydroxyisophthalate 
• 2937-59-9 2,6-bis(hydroxymethyl)phenol 
• 118203-17-1 2-hydroxy-3-(hydroxymethyl)benzaldehyde 
• 1422257-46-2 2-butoxyisophthalaldehyde 
• 849587-67-3 1,8-bis(2,6-diformylphenoxy)-3,6-dioxaoctane 
• 339245-78-2 2,6-diformyl-4-iodophenol 

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