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611-20-1

Basic Information
CAS No.: 611-20-1
Name: Benzonitrile,2-hydroxy-
Article Data: 247
Cas Database
Molecular Structure:
Molecular Structure of 611-20-1 (Benzonitrile,2-hydroxy-)
Formula: C7H5NO
Molecular Weight: 119.123
Synonyms: Salicylonitrile(6CI,7CI,8CI);2-Hydroxybenzonitrile;NSC 53558;Salicylnitrile;o-Cyanophenol;o-Hydroxybenzonitrile;
EINECS: 210-259-3
Density: 1.22 g/cm3
Melting Point: 92-95 °C(lit.)
Boiling Point: 273.1 °C at 760 mmHg
Flash Point: 109.6 °C
Solubility: soluble in water
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38-20/21/22
Safety: 26-36-45
Transport Information: UN 3276
PSA: 44.02000
LogP: 1.26388
Synthetic route
21013-96-7

(E)-2-hydroxylbenzaldehyde oxime

611-20-1

salicylonitrile

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 20℃; for 4h; Beckmann rearrangement;100%
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 1h; Solvent; Mitsunobu Displacement; Inert atmosphere;97%
With aluminum oxide; methanesulfonyl chloride at 100℃; for 0.0833333h;94%
394-47-8

2-fluorobenzonitrile

611-20-1

salicylonitrile

Conditions
ConditionsYield
With 2-(methylsulfonyl)ethyl alcohol; sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;100%
With methyl propargyl alcohol; potassium tert-butylate In dimethyl sulfoxide at 125℃; for 0.0333333h; microwave irradiation;73%
Multi-step reaction with 3 steps
1.1: 94 percent / NaH / dimethylformamide / 3 h / 70 °C
2.1: 7.08 g / ICl; K2CO3 / CH2Cl2 / 1 h / Heating
3.1: iPrMgCl / tetrahydrofuran / 0.52 h / -78 °C
3.2: ZnCl2 / tetrahydrofuran / -78 - 20 °C
3.3: Pd(PPh3)4 / tetrahydrofuran; dimethylformamide / 18 h / 20 °C
View Scheme
218797-78-5

2-(tert-butoxy)benzonitrile

611-20-1

salicylonitrile

Conditions
ConditionsYield
With sodium iodide; cerium(III) chloride In acetonitrile at 40℃; for 6h;100%
Multi-step reaction with 2 steps
1: potassium tert-butylate / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere; Sealed tube
2: potassium tert-butylate; 18-crown-6 ether; water / 1,4-dioxane / 16 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere; Sealed tube
2: potassium tert-butylate / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere; Sealed tube; Glovebox
3: potassium tert-butylate; 18-crown-6 ether; water / 1,4-dioxane / 16 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere; Sealed tube
2: potassium tert-butylate; 18-crown-6 ether / 1,4-dioxane / 16 h / 20 °C / Inert atmosphere; Sealed tube
3: potassium tert-butylate; 18-crown-6 ether; water / 1,4-dioxane / 16 h / 20 °C
View Scheme
94-67-7

salicylaldehyde-oxime

611-20-1

salicylonitrile

Conditions
ConditionsYield
With chlorosulfonic acid In toluene at 90℃; for 0.5h;99%
With oxalyl dichloride; Tropone; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 0.166667h; Schlenk technique; Inert atmosphere;99%
With acetyl chloride; zinc(II) oxide for 0.5h; Heating;95%
97960-34-4

2-(prop-2'-enyloxy)benzonitrile

611-20-1

salicylonitrile

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate; tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis: Mg rod anode, carbon fibre cathode, const. current 60 mA;99%
65211-56-5

2-(prop-2-yn-1-yloxy)benzonitrile

611-20-1

salicylonitrile

Conditions
ConditionsYield
tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis;99%
65-45-2

salicylamide

611-20-1

salicylonitrile

Conditions
ConditionsYield
With phosgene; L-lysine In 1,2-dichloro-ethane at 80℃; for 4h; Reagent/catalyst; Temperature;98.8%
With phosgene; cyanex-921 In 1,2-dichloro-ethane for 4h; Reagent/catalyst; Solvent; Reflux;98.9%
With thionyl chloride In 5,5-dimethyl-1,3-cyclohexadiene at 105℃; for 7h; Concentration; Temperature; Solvent; Reagent/catalyst;97.8%
118-61-6

2-hydroxy-benzoic acid ethyl ester

611-20-1

salicylonitrile

Conditions
ConditionsYield
With ammonia; boron phosphate at 400℃; for 0.000277778h;98%
Multi-step reaction with 2 steps
1: alcohol; ammonia / 100 °C
2: phosphorus pentoxide
View Scheme
Multi-step reaction with 2 steps
1: alcohol; ammonia / 100 °C
2: phosphorus pentoxide
View Scheme
Multi-step reaction with 3 steps
1: alcohol; ammonia / 100 °C
2: P2S5
3: bei der Destillation unter vermindertem Druck
View Scheme

2-hydroxy-benzaldehyde O-phenyl-oxime

611-20-1

salicylonitrile

Conditions
ConditionsYield
With zirconium(IV) chloride In nitromethane for 0.0333333h; Heating;97%
114536-52-6

salicylonitril; ammonium salt

611-20-1

salicylonitrile

Conditions
ConditionsYield
With ammonia; N,N-dimethyl-formamide; Xylene; mixture of at 420℃; Product distribution / selectivity;97%
With sulfuric acid; ammonia; water at 60℃; pH=3 - 4; Product distribution / selectivity;96%
With ammonia; Xylene; mixture of at 420℃; Product distribution / selectivity;94%
Stage #1: salicylonitril; ammonium salt With ammonia; water at 15 - 60℃;
Stage #2: In N,N-dimethyl-formamide at 60℃; under 37.5038 - 75.0075 Torr; Product distribution / selectivity;
72%
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Specification

The 2-Cyanophenol, with the CAS registry number 611-20-1, is also known as Salicylonitrile. It belongs to the product categories of Aromatic Nitriles; Miscellaneous. Its EINECS registry number is 210-259-3. This chemical's molecular formula is C7H5NO and molecular weight is 119.12. What's more, its IUPAC name is called 2-Hydroxybenzonitrile. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 2-Cyanophenol are: (1)ACD/LogP: 1.026; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.02; (4)ACD/LogD (pH 7.4): 0.60; (5)ACD/BCF (pH 5.5): 3.47; (6)ACD/BCF (pH 7.4): 1.32; (7)ACD/KOC (pH 5.5): 84.32; (8)ACD/KOC (pH 7.4): 31.98; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 44.02 Å2; (13)Index of Refraction: 1.591; (14)Molar Refractivity: 32.849 cm3; (15)Molar Volume: 97.264 cm3; (16)Surface Tension: 57.85 dyne/cm; (17)Density: 1.225 g/cm3; (18)Flash Point: 109.584 °C; (19)Enthalpy of Vaporization: 53.202 kJ/mol; (20)Boiling Point: 273.109 °C at 760 mmHg; (21)Vapour Pressure: 0.0030 mmHg at 25 °C.

Preparation of 2-Cyanophenol: this chemical can be prepared by Salicylaldehyde-(E)-oxime. This reaction needs reagent 2,4,6-trichloro[1,3,5]triazine and solvent dimethylformamide at temperature of 20 °C. The reaction time is 4 hours. The yield is 100 %.

2-Cyanophenol can be prepared by Salicylaldehyde-(E)-oxime.

Uses of 2-Cyanophenol: (1) it is used as bunitrolol intermediates; (2) it is used to produce other chemicals. For example, it can react with ethanol to get salicylimidic acid ethyl ester; hydrochloride. The reaction occurs with reagent HCl and solvent benzene at temperature of 20 °C. The reaction time is 15 days. The yield is 37 %.

2-Cyanophenol can react with ethanol to get salicylimidic acid ethyl ester; hydrochloride.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. It is harmful by inhalation, in contact with skin and if swallowed. Therefore, you should wear suitable protective clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1) SMILES: N#Cc1ccccc1O
(2) InChI: InChI=1S/C7H5NO/c8-5-6-3-1-2-4-7(6)9/h1-4,9H
(3) InChIKey: CHZCERSEMVWNHL-UHFFFAOYSA-N