Product Name

  • Name

    5-HYDROXY-ISOPHTHALONITRILE

  • EINECS
  • CAS No. 79370-78-8
  • Article Data15
  • CAS DataBase
  • Density 1.343 g/cm3
  • Solubility
  • Melting Point 266 °C
  • Formula C8H4N2O
  • Boiling Point 295.823 °C at 760 mmHg
  • Molecular Weight 144.133
  • Flash Point 132.709 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 79370-78-8 (5-HYDROXY-ISOPHTHALONITRILE)
  • Hazard Symbols
  • Synonyms 3,5-Dicyanohydroxybenzene;3,5-Dicyanophenol;5-Hydroxy-isophthalonitrile;
  • PSA 67.81000
  • LogP 1.13556

Synthetic route

5-hydroxy-benzene-1,3-dicarbonylamide
68052-43-7

5-hydroxy-benzene-1,3-dicarbonylamide

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
With trichlorophosphate In acetonitrile96%
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

4-nitro-phenol

5-nitrobenzene-1,3-dicarbonitrile
33224-18-9

5-nitrobenzene-1,3-dicarbonitrile

A

bis(4-nitrophenyl)ether
101-63-3

bis(4-nitrophenyl)ether

B

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

C

3,3',5,5'-tetracyanodiphenyl ether

3,3',5,5'-tetracyanodiphenyl ether

D

5-(4-Nitro-phenoxy)-isophthalonitrile
188998-65-4

5-(4-Nitro-phenoxy)-isophthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2.3h;A n/a
B n/a
C n/a
D 25%
...Expand
4-nitro-phenol
100-02-7

4-nitro-phenol

5-(4-Nitro-phenoxy)-isophthalonitrile
188998-65-4

5-(4-Nitro-phenoxy)-isophthalonitrile

A

bis(4-nitrophenyl)ether
101-63-3

bis(4-nitrophenyl)ether

B

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
With potassium carbonate at 120℃; for 7h;
...Expand
5-nitrobenzene-1,3-dicarbonitrile
33224-18-9

5-nitrobenzene-1,3-dicarbonitrile

4-nitrophenol sodium salt
824-78-2

4-nitrophenol sodium salt

A

bis(4-nitrophenyl)ether
101-63-3

bis(4-nitrophenyl)ether

B

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

C

5-(4-Nitro-phenoxy)-isophthalonitrile
188998-65-4

5-(4-Nitro-phenoxy)-isophthalonitrile

Conditions
ConditionsYield
Product distribution; various temperatures;
...Expand
4-cyanophenol
767-00-0

4-cyanophenol

5-(4-Cyano-phenoxy)-isophthalonitrile
188998-64-3

5-(4-Cyano-phenoxy)-isophthalonitrile

A

4-(4'-cyanophenoxy)benzonitrile
6508-04-9

4-(4'-cyanophenoxy)benzonitrile

B

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 150℃;
...Expand
5-nitro-1,3-benzenedicarbonylchloride
13438-30-7

5-nitro-1,3-benzenedicarbonylchloride

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
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-nitrobenzene-1,3-dicarboxylic acid

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
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-nitrobenzene-1,3-dicarbonitrile

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
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-methoxyisophthalonitrile

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
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-Hydroxyisophthalic acid

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
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-Hydroxybenzene-1,3-dicarbonyl dichloride

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
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

5-hydroxyisophthalonitrile

<2H9>trimethylsulphoxonium iodide
23726-00-3

<2H9>trimethylsulphoxonium iodide

5-(methoxy-d3)isophthalonitrile

5-(methoxy-d3)isophthalonitrile

Conditions
ConditionsYield
With potassium carbonate at 65℃; for 18h; Sealed tube;99%
ethyl (2,3-difluoro-4-nitrophenyl)acetate
317356-84-6

ethyl (2,3-difluoro-4-nitrophenyl)acetate

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

C18H12FN3O5
867366-79-8

C18H12FN3O5

Conditions
ConditionsYield
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

(2-chloro-pyridin-4-yl)-carbamic acid tert-butyl ester

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

C18H16N4O3

C18H16N4O3

Conditions
ConditionsYield
With C45H65FeNO3P2PdS; caesium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Sealed tube;76%
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

sodium-tetrakis(bis-3,5-cyano-phenoxy)-borate

sodium-tetrakis(bis-3,5-cyano-phenoxy)-borate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3h; Reflux;63%
4-chloro-3,5-heptanedione
13054-81-4

4-chloro-3,5-heptanedione

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

5-(2-oxo-1-propanoylbutoxy)isophthalonitrile
473924-01-5

5-(2-oxo-1-propanoylbutoxy)isophthalonitrile

Conditions
ConditionsYield
With caesium carbonate In acetone47%
With triethylamine In Isopropyl acetate Reflux;
5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

tert-butyl 4-bromobutyrate
110661-91-1

tert-butyl 4-bromobutyrate

tert-butyl 4-(3,5-dicyanophenoxy)butanoate

tert-butyl 4-(3,5-dicyanophenoxy)butanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 16h;42%
5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

3-chloropentane-2,4-dione
1694-29-7

3-chloropentane-2,4-dione

5-[(3, 5-dimethyl-1H-pyrazol-4-yl)oxy]-5-isophthalonitrile
676994-55-1

5-[(3, 5-dimethyl-1H-pyrazol-4-yl)oxy]-5-isophthalonitrile

Conditions
ConditionsYield
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

5-hydroxyisophthalonitrile

methyl 2-chloro-3-oxopentanoate
114192-09-5

methyl 2-chloro-3-oxopentanoate

2-(3,5-dicyano-phenoxy)-3-oxo-pentanoic acid methyl ester

2-(3,5-dicyano-phenoxy)-3-oxo-pentanoic acid methyl ester

Conditions
ConditionsYield
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

(4E)-1-(benzyloxy)-4-chloro-5-hydroxy-4-hepten-3-one

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

5-({(1E)-1-[3-(benzyloxy)propanoyl]-2-hydroxy-1-butenyl}oxy)isophthalonitrile
473924-11-7

5-({(1E)-1-[3-(benzyloxy)propanoyl]-2-hydroxy-1-butenyl}oxy)isophthalonitrile

Conditions
ConditionsYield
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

2-chloro-1-cyclopropylbutane-1,3-dione

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

5-[1-(cyclopropylcarbonyl)-2-oxopropoxy]isophtalonitrile
675198-31-9

5-[1-(cyclopropylcarbonyl)-2-oxopropoxy]isophtalonitrile

Conditions
ConditionsYield
With caesium carbonate In acetone at 60℃; for 3h;
5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

5-(4-methylthiopyrimidin-2-yloxy)isophthalonitrile
548466-06-4

5-(4-methylthiopyrimidin-2-yloxy)isophthalonitrile

Conditions
ConditionsYield
With potassium carbonate In water; ethyl acetate; N,N-dimethyl-formamide
2,4-bis(3-chloro-4-cyanophenoxy)pyrimidine
548466-09-7

2,4-bis(3-chloro-4-cyanophenoxy)pyrimidine

5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

5-[2-(3-chloro-4-cyanophenoxy)pyrimidin-4-yloxy]isophthalonitrile
548466-02-0

5-[2-(3-chloro-4-cyanophenoxy)pyrimidin-4-yloxy]isophthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide
5-hydroxyisophthalonitrile
79370-78-8

5-hydroxyisophthalonitrile

N,N-Dimethylthiocarbamoyl chloride
16420-13-6

N,N-Dimethylthiocarbamoyl chloride

O-(3,5-dicyanophenyl)dimethylthiocarbamate
868525-05-7

O-(3,5-dicyanophenyl)dimethylthiocarbamate

Conditions
ConditionsYield
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

5-hydroxyisophthalonitrile

4-(3,5-dicyanophenoxy)butanoic acid

4-(3,5-dicyanophenoxy)butanoic acid

Conditions
ConditionsYield
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

5-hydroxyisophthalonitrile

4-(3,5-dicyanophenoxy)-N-(5-methylthiazol-2-yl)butanamide

4-(3,5-dicyanophenoxy)-N-(5-methylthiazol-2-yl)butanamide

Conditions
ConditionsYield
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

1,3-Benzenedicarbonitrile,5-hydroxy- Specification

The 1,3-Benzenedicarbonitrile,5-hydroxy-, with the CAS registry number 79370-78-8, is also known as 3,5-Dicyanophenol. It belongs to the product category of Aromatics. This chemical's molecular formula is C8H4N2O and molecular weight is 144.13. What's more, its IUPAC name is 5-Hydroxybenzene-1,3-dicarbonitrile.

Physical properties about 1,3-Benzenedicarbonitrile,5-hydroxy-: (1)ACD/LogP: 1.651; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.64; (4)ACD/LogD (pH 7.4): 1.24; (5)ACD/BCF (pH 5.5): 10.38; (6)ACD/BCF (pH 7.4): 4.08; (7)ACD/KOC (pH 5.5): 184.74; (8)ACD/KOC (pH 7.4): 72.59; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 67.81 Å2; (13)Index of Refraction: 1.614; (14)Molar Refractivity: 37.416 cm3; (15)Molar Volume: 107.3 cm3; (16)Polarizability: 14.833×10-24cm3; (17)Surface Tension: 75.122 dyne/cm; (18)Density: 1.343 g/cm3; (19)Flash Point: 132.709 °C; (20)Enthalpy of Vaporization: 55.7 kJ/mol; (21)Boiling Point: 295.823 °C at 760 mmHg; (22)Vapour Pressure: 0.001 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1) SMILES: N#Cc1cc(cc(O)c1)C#N
(2) InChI: InChI=1S/C8H4N2O/c9-4-6-1-7(5-10)3-8(11)2-6/h1-3,11H
(3) InChIKey: CHASTCUDJNQBOZ-UHFFFAOYSA-N

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