79370-78-8

Basic information

• Product Name: 5-HYDROXY-ISOPHTHALONITRILE
• Synonyms: 1,3-BENZENEDICARBONITRILE, 5-HYDROXY-;5-HYDROXY-ISOPHTHALONITRILE;3,5-Dicyanohydroxybenzene;5-hydroxy-1,3-Benzenedicarbonitrile;5-hydroxybenzene-1,3-dicarbonitrile
• CAS NO: 79370-78-8
• Molecular Formula: C₈H₄N₂O
• Molecular Weight: 144.133
• Mol File: 79370-78-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 266 °C
• Boiling Point: 295.823 °C at 760 mmHg
• Flash Point: 132.709 °C
• Appearance: /
• Density: 1.343 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.20±0.10(Predicted)
• CAS DataBase Reference: 5-HYDROXY-ISOPHTHALONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXY-ISOPHTHALONITRILE(79370-78-8)
• EPA Substance Registry System: 5-HYDROXY-ISOPHTHALONITRILE(79370-78-8)

Safety Data

• Hazardous Substances Data: 79370-78-8(Hazardous Substances Data)

Usage

Uses

5-Hydroxyisophthalonitrile

InChI:InChI=1/C8H4N2O/c9-4-6-1-7(5-10)3-8(11)2-6/h1-3,11H

Synthetic route

5-hydroxy-benzene-1,3-dicarbonylamide (68052-43-7) → 5-hydroxyisophthalonitrile (79370-78-8)

Conditions	Yield
With trichlorophosphate In acetonitrile	96%
With trichlorophosphate In N,N-dimethyl-formamide at 0 - 45℃; for 4h; Schlenk technique; Cooling with ice;	74%
at 345℃; for 1h; Temperature;
With phosphorus pentoxide under 15.0015 - 37.5038 Torr; for 1h; Temperature; Heating;

4-nitro-phenol (100-02-7) + 5-nitrobenzene-1,3-dicarbonitrile (33224-18-9) → bis(4-nitrophenyl)ether (101-63-3) + 5-hydroxyisophthalonitrile (79370-78-8) + 3,3',5,5'-tetracyanodiphenyl ether + 5-(4-Nitro-phenoxy)-isophthalonitrile (188998-65-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2.3h;	A n/a B n/a C n/a D 25%

4-nitro-phenol (100-02-7) + 5-(4-Nitro-phenoxy)-isophthalonitrile (188998-65-4) → bis(4-nitrophenyl)ether (101-63-3) + 5-hydroxyisophthalonitrile (79370-78-8)

Conditions	Yield
With potassium carbonate at 120℃; for 7h;

5-nitrobenzene-1,3-dicarbonitrile (33224-18-9) + 4-nitrophenol sodium salt (824-78-2) → bis(4-nitrophenyl)ether (101-63-3) + 5-hydroxyisophthalonitrile (79370-78-8) + 5-(4-Nitro-phenoxy)-isophthalonitrile (188998-65-4)

Conditions	Yield
Product distribution; various temperatures;

4-cyanophenol (767-00-0) + 5-(4-Cyano-phenoxy)-isophthalonitrile (188998-64-3) → 4-(4'-cyanophenoxy)benzonitrile (6508-04-9) + 5-hydroxyisophthalonitrile (79370-78-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃;

5-nitro-1,3-benzenedicarbonylchloride (13438-30-7) → 5-hydroxyisophthalonitrile (79370-78-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent 2: K2CO3 / dimethylformamide / 2.3 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: 76 percent 2: 25 percent / K2CO3 / dimethylformamide / 2.3 h / 100 °C 3: K2CO3 / 7 h / 120 °C View Scheme
Multi-step reaction with 3 steps 1: 76 percent 2: 70 percent / K2CO3 / dimethylformamide / 3 h / 100 °C 3: K2CO3 / dimethylformamide / 150 °C View Scheme

5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → 5-hydroxyisophthalonitrile (79370-78-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: Cl-X 2: 76 percent 3: K2CO3 / dimethylformamide / 2.3 h / 100 °C View Scheme
Multi-step reaction with 4 steps 1: Cl-X 2: 76 percent 3: 25 percent / K2CO3 / dimethylformamide / 2.3 h / 100 °C 4: K2CO3 / 7 h / 120 °C View Scheme
Multi-step reaction with 4 steps 1: Cl-X 2: 76 percent 3: 70 percent / K2CO3 / dimethylformamide / 3 h / 100 °C 4: K2CO3 / dimethylformamide / 150 °C View Scheme

5-nitrobenzene-1,3-dicarbonitrile (33224-18-9) → 5-hydroxyisophthalonitrile (79370-78-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 25 percent / K2CO3 / dimethylformamide / 2.3 h / 100 °C 2: K2CO3 / 7 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: 70 percent / K2CO3 / dimethylformamide / 3 h / 100 °C 2: K2CO3 / dimethylformamide / 150 °C View Scheme

5-methoxyisophthalonitrile (453565-53-2) → 5-hydroxyisophthalonitrile (79370-78-8)

Conditions	Yield
Stage #1: 5-methoxyisophthalonitrile With aluminum (III) chloride In dichloromethane at 0 - 45℃; for 144h; Stage #2: With hydrogenchloride In dichloromethane; water at 20℃; for 0.166667h;
Stage #1: 5-methoxyisophthalonitrile With aluminum (III) chloride In dichloromethane at 0 - 45℃; for 144h; Stage #2: With hydrogenchloride In water at 20℃; for 0.166667h;
Stage #1: 5-methoxyisophthalonitrile With aluminum (III) chloride In dichloromethane at 0 - 45℃; for 144h; Stage #2: With hydrogenchloride In water at 20℃; for 0.166667h;

5-Hydroxyisophthalic acid (618-83-7) → 5-hydroxyisophthalonitrile (79370-78-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / tetrahydrofuran; N,N-dimethyl-formamide / Schlenk technique; Reflux 2: ammonium hydroxide / tetrahydrofuran / -40 °C 3: trichlorophosphate / N,N-dimethyl-formamide / 4 h / 0 - 45 °C / Schlenk technique; Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: ammonium / 0.5 h / Heating 2: phosphorus pentoxide / 1 h / 15 - 37.5 Torr / Heating View Scheme

5-Hydroxybenzene-1,3-dicarbonyl dichloride (61842-44-2) → 5-hydroxyisophthalonitrile (79370-78-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium hydroxide / tetrahydrofuran / -40 °C 2: trichlorophosphate / N,N-dimethyl-formamide / 4 h / 0 - 45 °C / Schlenk technique; Cooling with ice View Scheme

5-hydroxyisophthalonitrile (79370-78-8) + <2H9>trimethylsulphoxonium iodide (23726-00-3) → 5-(methoxy-d3)isophthalonitrile

Conditions	Yield
With potassium carbonate at 65℃; for 18h; Sealed tube;	99%

ethyl (2,3-difluoro-4-nitrophenyl)acetate (317356-84-6) + 5-hydroxyisophthalonitrile (79370-78-8) → C18H12FN3O5 (867366-79-8)

Conditions	Yield
Stage #1: 5-hydroxyisophthalonitrile With sodium t-butanolate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: ethyl (2,3-difluoro-4-nitrophenyl)acetate In tetrahydrofuran for 3h; Stage #3: With hydrogenchloride; water In tetrahydrofuran	78%

(2-chloro-pyridin-4-yl)-carbamic acid tert-butyl ester (234108-73-7) + 5-hydroxyisophthalonitrile (79370-78-8) → C18H16N4O3

Conditions	Yield
With C45H65FeNO3P2PdS; caesium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Sealed tube;	76%

sodium tetrahydroborate (16940-66-2) + 5-hydroxyisophthalonitrile (79370-78-8) → sodium-tetrakis(bis-3,5-cyano-phenoxy)-borate

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h; Reflux;	63%

4-chloro-3,5-heptanedione (13054-81-4) + 5-hydroxyisophthalonitrile (79370-78-8) → 5-(2-oxo-1-propanoylbutoxy)isophthalonitrile (473924-01-5)

Conditions	Yield
With caesium carbonate In acetone	47%
With triethylamine In Isopropyl acetate Reflux;

5-hydroxyisophthalonitrile (79370-78-8) + tert-butyl 4-bromobutyrate (110661-91-1) → tert-butyl 4-(3,5-dicyanophenoxy)butanoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 16h;	42%

5-hydroxyisophthalonitrile (79370-78-8) + 3-chloropentane-2,4-dione (1694-29-7) → 5-[(3, 5-dimethyl-1H-pyrazol-4-yl)oxy]-5-isophthalonitrile (676994-55-1)

Conditions	Yield
Stage #1: 5-hydroxyisophthalonitrile; 3-chloropentane-2,4-dione With cesium carbonate In acetone at 65℃; for 2h; Stage #2: With hydrogenchloride In water; acetone at 20℃; Stage #3: With acetic acid; hydrazine at 20℃; for 0.166667h;
Stage #1: 5-hydroxyisophthalonitrile; 3-chloropentane-2,4-dione With caesium carbonate at 65℃; for 2h; Stage #2: With acetic acid; hydrazine at 20℃; for 0.166667h;

5-hydroxyisophthalonitrile (79370-78-8) + methyl 2-chloro-3-oxopentanoate (114192-09-5) → 2-(3,5-dicyano-phenoxy)-3-oxo-pentanoic acid methyl ester

Conditions	Yield
With caesium carbonate In acetone at 20℃; for 2.75h; Heating / reflux;

(4E)-1-(benzyloxy)-4-chloro-5-hydroxy-4-hepten-3-one (473924-09-3) + 5-hydroxyisophthalonitrile (79370-78-8) → 5-({(1E)-1-[3-(benzyloxy)propanoyl]-2-hydroxy-1-butenyl}oxy)isophthalonitrile (473924-11-7)

Conditions	Yield
With caesium carbonate In acetone at 20℃; for 2h; Heating / reflux;
With caesium carbonate In acetone for 2h; Heating / reflux;

2-chloro-1-cyclopropylbutane-1,3-dione (473924-31-1) + 5-hydroxyisophthalonitrile (79370-78-8) → 5-[1-(cyclopropylcarbonyl)-2-oxopropoxy]isophtalonitrile (675198-31-9)

Conditions	Yield
With caesium carbonate In acetone at 60℃; for 3h;

5-hydroxyisophthalonitrile (79370-78-8) → 5-(4-methylthiopyrimidin-2-yloxy)isophthalonitrile (548466-06-4)

Conditions	Yield
With potassium carbonate In water; ethyl acetate; N,N-dimethyl-formamide

2,4-bis(3-chloro-4-cyanophenoxy)pyrimidine (548466-09-7) + 5-hydroxyisophthalonitrile (79370-78-8) → 5-[2-(3-chloro-4-cyanophenoxy)pyrimidin-4-yloxy]isophthalonitrile (548466-02-0)

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

5-hydroxyisophthalonitrile (79370-78-8) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-(3,5-dicyanophenyl)dimethylthiocarbamate (868525-05-7)

Conditions	Yield
Stage #1: 5-hydroxyisophthalonitrile With sodium carbonate In 1-methyl-pyrrolidin-2-one at 0 - 20℃; for 0.5h; Stage #2: N,N-Dimethylthiocarbamoyl chloride In 1-methyl-pyrrolidin-2-one at 20 - 70℃; for 16.5h;

5-hydroxyisophthalonitrile (79370-78-8) → 4-(3,5-dicyanophenoxy)butanoic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C 2: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C View Scheme

5-hydroxyisophthalonitrile (79370-78-8) → 4-(3,5-dicyanophenoxy)-N-(5-methylthiazol-2-yl)butanamide

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C 2: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 16 h / 45 °C View Scheme

Upstream product

• 100-02-7 4-nitro-phenol 
• 33224-18-9 5-nitrobenzene-1,3-dicarbonitrile 
• 188998-65-4 5-(4-Nitro-phenoxy)-isophthalonitrile 
• 824-78-2 4-nitrophenol sodium salt 
• 767-00-0 4-cyanophenol 
• 188998-64-3 5-(4-Cyano-phenoxy)-isophthalonitrile 
• 13438-30-7 5-nitro-1,3-benzenedicarbonylchloride 
• 618-88-2 5-nitrobenzene-1,3-dicarboxylic acid 
• 453565-53-2 5-methoxyisophthalonitrile 
• 68052-43-7 5-hydroxy-benzene-1,3-dicarbonylamide 
• 618-83-7 5-Hydroxyisophthalic acid 
• 61842-44-2 5-Hydroxybenzene-1,3-dicarbonyl dichloride 

Downstream Products

• 676994-55-1 5-[(3, 5-dimethyl-1H-pyrazol-4-yl)oxy]-5-isophthalonitrile 
• 473924-11-7 5-({(1E)-1-[3-(benzyloxy)propanoyl]-2-hydroxy-1-butenyl}oxy)isophthalonitrile 
• 675198-31-9 5-[1-(cyclopropylcarbonyl)-2-oxopropoxy]isophtalonitrile 
• 548466-06-4 5-(4-methylthiopyrimidin-2-yloxy)isophthalonitrile 
• 867366-79-8 C₁₈H₁₂FN₃O₅ 
• 868525-05-7 O-(3,5-dicyanophenyl)dimethylthiocarbamate 
• 473924-01-5 5-(2-oxo-1-propanoylbutoxy)isophthalonitrile 

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