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79370-78-8

Basic Information
CAS No.: 79370-78-8
Name: 5-HYDROXY-ISOPHTHALONITRILE
Article Data: 15
Molecular Structure:
Molecular Structure of 79370-78-8 (5-HYDROXY-ISOPHTHALONITRILE)
Formula: C8H4N2O
Molecular Weight: 144.133
Synonyms: 3,5-Dicyanohydroxybenzene;3,5-Dicyanophenol;5-Hydroxy-isophthalonitrile;
Density: 1.343 g/cm3
Melting Point: 266 °C
Boiling Point: 295.823 °C at 760 mmHg
Flash Point: 132.709 °C
PSA: 67.81000
LogP: 1.13556
Synthetic route
68052-43-7

5-hydroxy-benzene-1,3-dicarbonylamide

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;
100-02-7

4-nitro-phenol

33224-18-9

5-nitrobenzene-1,3-dicarbonitrile

A

101-63-3

bis(4-nitrophenyl)ether

B

79370-78-8

5-hydroxyisophthalonitrile

C

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

D

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%
100-02-7

4-nitro-phenol

188998-65-4

5-(4-Nitro-phenoxy)-isophthalonitrile

A

101-63-3

bis(4-nitrophenyl)ether

B

79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
With potassium carbonate at 120℃; for 7h;
33224-18-9

5-nitrobenzene-1,3-dicarbonitrile

824-78-2

4-nitrophenol sodium salt

A

101-63-3

bis(4-nitrophenyl)ether

B

79370-78-8

5-hydroxyisophthalonitrile

C

188998-65-4

5-(4-Nitro-phenoxy)-isophthalonitrile

Conditions
ConditionsYield
Product distribution; various temperatures;
767-00-0

4-cyanophenol

188998-64-3

5-(4-Cyano-phenoxy)-isophthalonitrile

A

6508-04-9

4-(4'-cyanophenoxy)benzonitrile

B

79370-78-8

5-hydroxyisophthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 150℃;
13438-30-7

5-nitro-1,3-benzenedicarbonylchloride

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
618-88-2

5-nitrobenzene-1,3-dicarboxylic acid

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
33224-18-9

5-nitrobenzene-1,3-dicarbonitrile

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
453565-53-2

5-methoxyisophthalonitrile

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;
618-83-7

5-Hydroxyisophthalic acid

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
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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