2-Cyanophenol Property

Melting point:

92-95 °C (lit.)

Boiling point:

149 °C/14 mmHg (lit.)

Density 

1.1052

vapor pressure 

0.17Pa at 25℃

refractive index 

1.5372

Flash point:

149°C/14mm

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Crystalline Powder

pka

6.86(at 25℃)

color 

Off-white to brown

Water Solubility 

soluble

BRN 

1210029

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases.

LogP

1.66 at 30℃

CAS DataBase Reference

611-20-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzonitrile, 2-hydroxy-(611-20-1)

EPA Substance Registry System

Benzonitrile, 2-hydroxy- (611-20-1)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36-45

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29269095

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

2-Cyanophenol Chemical Properties,Usage,Production

Description

Cyanophenol is a vital molecule widely used to synthesize liquid crystal materials, medicines, spices, pesticides, corrosion inhibitors, etc. Cyanophenol is formed by substituting two hydrogen atoms of benzene molecules with hydroxyl and cyano groups, respectively. The cyano and hydroxyl groups are in the ring plane in the stable molecular structure. The hydroxyl group can have two different orientations relative to the cyano group. 2-cyanophenol, one of the Cyanophenol, is an essential ingredient in pesticides, spices, liquid crystal materials, etc. It is an especially critical intermediate for synthesizing methoxyacrylate fungicide mystrostrobin, widely used in agrochemicals, pharmaceutical chemicals, and other industries. The cyano group can strongly attract electrons. Replacing a hydrogen atom of the benzene ring by the cyano group usually increases the ionization energy (IE)[1].

Chemical Properties

2-Cyanophenol is a white to light yellow crystal powder with a pungent and bitter odor. It is partially soluble in water with a Pka value of 7.17. However, it is unstable when exposed to strong alkalis and oxidants. It is an important intermediate for the synthesis of the fungicide azoxystrobin and the antihypertensive drug Bunirolol.

Uses

2-Hydroxybenzonitrile is used as starting reagent during the synthesis of mono-alkoxyphenyloxazoline, furanoside.

Preparation

A method for preparing 2-cyanophenol, which comprises the following steps: preparing salicylaldoxime; performing dehydration; and performing hydrolytic-acidification reaction, wherein in the dehydration, anhydride is adopted as a dehydrating agent; and in the hydrolytic-acidification reaction, a hydrolyticreagent is 10 to 30 mass percent alkaline solution, and the temperature of the hydrolytic-acidification reaction is 100 to 150℃.

Definition

ChEBI: 2-Cyanophenol is a member of benzenes and a nitrile.

Application

2-Cyanophenol is used in the synthesis of CDK/GSK-3 inhibitors, for usage as therapeutics in Alzheimer's disease (AD).

Flammability and Explosibility

Not classified

Synthesis

2-Hydroxybenzonitrile can be synthesized by condensing salicylaldehyde with hydroxylamine hydrochloride to produce salicylaldoxime. Then, the salicylaldoxime is reacted with acetic anhydride followed by hydrolysis to yield 2-Hydroxybenzonitrile.
Process for the preparation of 2-hydroxybenzonitrile

storage

Store at 2°C - 8°C, close container well, protect from light.                                   

References

[1] Na Li. “Vibrational spectra of 2-cyanophenol cation studied by the mass analyzed threshold ionization technique.” Chemical Physics Letters 792 (2022): Article 139402.