300853-66-1

Basic information

• Product Name: 4,5-Dihydroxy-1,2-benzenedicarbonitrile
• Synonyms: 1,2-BENZENEDICARBONITRILE, 4,5-DIHYDROXY-;4,5-dihydroxy, 2-benzenedicarbonitrile;4,5-Dihydroxyphthalonitrile;4,5-Dihydroxy-1,2-Benzenedicar;4,5-Dihydroxy-1,2-benzenedicarbonitrile
• CAS NO: 300853-66-1
• Molecular Formula: C₈H₄N₂O₂
• Molecular Weight: 160.13
• Mol File: 300853-66-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 462.676 °C at 760 mmHg
• Flash Point: 233.619 °C
• Appearance: /
• Density: 1.533 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.00±0.23(Predicted)
• CAS DataBase Reference: 4,5-Dihydroxy-1,2-benzenedicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dihydroxy-1,2-benzenedicarbonitrile(300853-66-1)
• EPA Substance Registry System: 4,5-Dihydroxy-1,2-benzenedicarbonitrile(300853-66-1)

Safety Data

• Hazardous Substances Data: 300853-66-1(Hazardous Substances Data)

Usage

General Description

4,5-Dihydroxy-1,2-benzenedicarbonitrile, also known as 4,5-Dihydroxy-o-phthalonitrile, is a chemical compound with the molecular formula C8H4N2O2. It is a crystalline solid that is often used in the synthesis of heterocycles and pharmaceuticals. 4,5-Dihydroxy-1,2-benzenedicarbonitrile is a derivative of phthalonitrile and contains two hydroxyl groups attached to a benzene ring with two nitrile groups. The presence of hydroxyl and nitrile groups makes it a versatile building block for the production of various organic compounds. It is also used as a chemical reagent in organic synthesis and in the manufacture of dyes and pigments. 4,5-Dihydroxy-1,2-benzenedicarbonitrile is a valuable compound in the chemical industry due to its reactivity and potential applications in the production of various products.

InChI:InChI=1/C8H4N2O2/c9-3-5-1-7(11)8(12)2-6(5)4-10/h1-2,11-12H

Synthetic route

2,2-dimethyl-benzo[1,3]dioxole-5,6-dicarbonitrile (114414-26-5) → 4,5-dihydroxyphthalonitrile (300853-66-1)

Conditions	Yield
With hydrogenchloride In ethanol for 3h; Heating;	100%
With sulfuric acid	90%

1,2-dibenzyloxy-4,5-dicyanobenzene (206995-45-1) → 4,5-dihydroxyphthalonitrile (300853-66-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; for 4h; Catalytic hydrogenation; debenzylation;	91%

5,6-dibromo-2,2-dimethyl-benzo[1,3]dioxole (114414-23-2) → 4,5-dihydroxyphthalonitrile (300853-66-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 36 percent / dimethylformamide / 3.5 h / Heating 2: 90 percent / H2SO4 View Scheme

4,5-dibromobenzene-1,2-diol (2563-26-0) → 4,5-dihydroxyphthalonitrile (300853-66-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / K2CO3 / ethanol / 8 h / Heating 2: 60 percent / dimethylformamide / 21 h / Heating 3: 91 percent / H2 / 10 percent Pd-C / ethyl acetate / 4 h / 20 °C View Scheme

1,2-bis(benzyloxy)-4,5-dibromobenzene (206995-42-8) → 4,5-dihydroxyphthalonitrile (300853-66-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / dimethylformamide / 21 h / Heating 2: 91 percent / H2 / 10 percent Pd-C / ethyl acetate / 4 h / 20 °C View Scheme

phosgene (75-44-5) + carbon tetrabromide (558-13-4) + 4,5-dihydroxyphthalonitrile (300853-66-1) → C11H4N2O

Conditions	Yield
With acetic acid Heating;	88%

phenyl trimethylsiloxane (2996-92-1) + triethylamine (121-44-8) + 4,5-dihydroxyphthalonitrile (300853-66-1) → triethylammonium bis(4,5-dihydroxyphthalonitrilecatecholato)phenylsilicate

Conditions	Yield
With potassium methanolate In tetrahydrofuran for 20h; Reflux;	59%

1-bromo-4-butene (5162-44-7) + 4,5-dihydroxyphthalonitrile (300853-66-1) → 4,5-bis(but-3-enyloxy)phthalonitrile

Conditions	Yield
With perhydrodibenzo-18-crown-6; potassium carbonate 1.) MEK, reflux, 72 h, 2.) MEK, reflux, 48 h; Yield given. Multistep reaction;

dimethyl 4,5-bis(dibromomethyl)phthalate + 4,5-dihydroxyphthalonitrile (300853-66-1) → 2,3-dicyano-6,11-dihydro-5,12-dioxa-dibenzo[a,e]cyclooctene-8,9-dicarboxylic acid dimethyl ester (1300042-53-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere;

3,4-bis(chloromethyl)-2,5-dimethylthiophene (5368-70-7) + 4,5-dihydroxyphthalonitrile (300853-66-1) → C16H12N2O2S (1300042-62-9)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃;

2,3-bis(chloromethyl)pyridine hydrochloride (27221-49-4) + 4,5-dihydroxyphthalonitrile (300853-66-1) → 5,12-dihydrobenzo[2,3][1,4]dioxocino[6,7-b]pyridine-8,9-dicarbonitrile (1300042-55-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.5h; Inert atmosphere;

3-hydroxymethyl-4-hydroxybutanal diethyl acetal (55387-85-4) + 4,5-dihydroxyphthalonitrile (300853-66-1) → 3-(2,2-diethoxyethyl)-3,4-dihydro-2H-benzo[b][1,4]dioxepine-7,8-dicarbonitrile (1300042-58-3)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 75℃; Mitsunobu reaction;

N,N-bis(2-hydroxyethyl)-O-tert-butylcarbamate (103898-11-9) + 4,5-dihydroxyphthalonitrile (300853-66-1) → C17H19N3O4 (1300042-67-4)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 80℃; Mitsunobu reaction;

4,5-dihydroxyphthalonitrile (300853-66-1) → 3-(2,2-diethoxyethyl)-3,4,8,9-tetrahydro-[1,4]dioxepino[2,3-f]isoindol-7(2H)-imine (1300042-59-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 75 °C 2: hydrogen / platinum(IV) oxide / methanol / 24 h / 20 °C / 1810.07 Torr View Scheme

4,5-dihydroxyphthalonitrile (300853-66-1) → tert-butyl 10-(2-(3-tert-butyl-4-methoxy-5-morpholinophenyl)-2-oxoethyl)-9-imino-2,3,5,6,10,11-hexahydro-[1,4,7]dioxazonino[2,3-f]isoindole-4(9H)-carboxylate (1300042-69-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 80 °C 2: hydrogen / platinum(IV) oxide / methanol / 24 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C View Scheme

4,5-dihydroxyphthalonitrile (300853-66-1) → 2-(8-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl)-7-imino-2,3,4,7,8,9-hexahydro-[1,4]dioxepino[2,3-f]isoindol-3-yl)acetaldehyde trifluoroacetate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 75 °C 2.1: hydrogen / platinum(IV) oxide / methanol / 24 h / 20 °C / 1810.07 Torr 3.1: N,N-dimethyl-formamide / 18 h / 20 °C 3.2: 0 °C View Scheme

4,5-dihydroxyphthalonitrile (300853-66-1) → C16H16N2O2S (1300042-63-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 80 °C 2: hydrogen / platinum(IV) oxide / methanol / 24 h / 20 °C View Scheme

4,5-dihydroxyphthalonitrile (300853-66-1) → C17H23N3O4 (1300042-68-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 80 °C 2: hydrogen / platinum(IV) oxide / methanol / 24 h / 20 °C View Scheme

4,5-dihydroxyphthalonitrile (300853-66-1) → 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(3-(2-(dimethylamino)ethyl)-7-imino-3,4-dihydro-[1,4]dioxepino[2,3-f]isoindol-8(2H,7H,9H)-yl)ethanone (1300041-64-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 75 °C 2.1: hydrogen / platinum(IV) oxide / methanol / 24 h / 20 °C / 1810.07 Torr 3.1: N,N-dimethyl-formamide / 18 h / 20 °C 3.2: 0 °C 4.1: acetic acid / 1,2-dichloro-ethane; tetrahydrofuran / 3 h / 20 °C 4.2: 1 h / 20 °C View Scheme

4,5-dihydroxyphthalonitrile (300853-66-1) → C32H38N2O4S (1300042-10-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 80 °C 2: hydrogen / platinum(IV) oxide / methanol / 24 h / 20 °C 3: N,N-dimethyl-formamide / 18 h / 20 °C View Scheme

1-bromo-octane (111-83-1) + 4,5-dihydroxyphthalonitrile (300853-66-1) → 1,2-dicyano-4,5-bis(n-octyloxy)benzene (118132-11-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h;

4,5-dihydroxyphthalonitrile (300853-66-1) + hexadecanyl bromide (112-82-3) → 4,5-bis(hexadecyloxy)phthalonitrile (118132-14-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h;

tosylethylazide (113738-22-0) + 4,5-dihydroxyphthalonitrile (300853-66-1) → C12H10N8O2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	120 mg

Upstream product

• 114414-26-5 2,2-dimethyl-benzo[1,3]dioxole-5,6-dicarbonitrile 
• 206995-42-8 1,2-bis(benzyloxy)-4,5-dibromobenzene 
• 2563-26-0 4,5-dibromobenzene-1,2-diol 
• 114414-23-2 5,6-dibromo-2,2-dimethyl-benzo[1,3]dioxole 
• 206995-45-1 1,2-dibenzyloxy-4,5-dicyanobenzene 

Downstream Products

• 1300042-69-6 tert-butyl 10-(2-(3-tert-butyl-4-methoxy-5-morpholinophenyl)-2-oxoethyl)-9-imino-2,3,5,6,10,11-hexahydro-[1,4,7]dioxazonino[2,3-f]isoindole-4(9H)-carboxylate 
• 1300041-64-8 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(3-(2-(dimethylamino)ethyl)-7-imino-3,4-dihydro-[1,4]dioxepino[2,3-f]isoindol-8(2H,7H,9H)-yl)ethanone 
• 1300042-10-7 C₃₂H₃₈N₂O₄S 
• 118132-11-9 1,2-dicyano-4,5-bis(n-octyloxy)benzene 
• 118132-14-2 4,5-bis(hexadecyloxy)phthalonitrile 

Relevant articles and documents

Synthesis of 4,5-dihydroxyphthalonitrile

4,5-Dihydroxyphthalonitrile was synthesized from pyrocatechol in a simple way. The compound obtained is a convenient starting reagent for the preparation of 4,5-dialkoxyphthalonitriles.

Self-assembled monolayers of phthalocyanine derivatives on glass and silicon

The synthesis of three phthalocyanine derivatives functionalised with seven or eight substituents including either one or two trichlorosilylalkyl chains is described. Self-assembled monolayers of the derivatives covalently bound to silicon and glass have been formed and characterised by FTIR and visible region spectroscopies.