4-Cyanophenol Chemical Properties

Melting point:

110-113 °C(lit.)

Boiling point:

146 °C / 2mmHg

Density 

1.1871 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

methanol: 0.1 g/mL, clear

form 

Crystalline Powder

pka

7.97(at 25℃)

color 

Off-white to beige-gray

Water Solubility 

slightly soluble

BRN 

386130

Stability:

Stable. Incompatible with strong oxidizing agents.

CAS DataBase Reference

767-00-0(CAS DataBase Reference)

NIST Chemistry Reference

4-Hydroxybenzoic acid nitrile(767-00-0)

EPA Substance Registry System

Benzonitrile, 4-hydroxy- (767-00-0)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36-45-24/25

WGK Germany 

3

RTECS 

DI4375000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29269095

MSDS

• Language:English Provider:4-Hydroxybenzonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Cyanophenol Usage And Synthesis

Chemical Properties

white crystalline powder or chips. 4-Hydroxybenzonitrile [767-00-0], 4-cyanophenol, 1-cyano-4-hydroxybenzene, Mr 119.2, forms colorless crystals of mp 113℃. 4-Hydroxybenzonitrile is produced by reaction of 4-bromophenol with copper (I) cyanide, by ammoxidation of p-cresol, by reaction of 4-chlorobenzonitrile with sodium methoxide, or by the catalyzed gas phase reaction of ethyl 4-hydroxybenzoate with ammonia. The nitrile is used for the production of the herbicides 3,5-dibromo- and 3,5-diiodo-4- hydroxybenzonitrile (Bromoxynil, Ioxynil, May & Baker).

Uses

Intermediates of Liquid Crystals

Uses

4-Cyanophenol is a precursor for the synthesis of a vasodilator, Levcromakalim. Bromination of 4-cyanophenol results in bromoxynil, a commercial herbicide. It can also be used as a component of deep eutectic solvent (DES) mixture.

Preparation

4-Cyanophenol is produced by reaction of 4-bromophenol with copper (I) cyanide, by ammoxidation of p-cresol, by reaction of 4-chlorobenzonitrile with sodium methoxide, or by the catalyzed gas phase reaction of ethyl 4-hydroxybenzoate with ammonia.

Definition

ChEBI: 4-cyanophenol is a member of phenols. It has a role as an EC 1.4.3.4 (monoamine oxidase) inhibitor. It is functionally related to a benzonitrile.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 3343, 1974 DOI: 10.1021/jo00937a007

Purification Methods

Crystallise the phenol from pet ether, *benzene or water and keep it under vacuum over P2O5. [Bernasconi & Paschelis J Am Chem Soc 108 2969 1986.] [Beilstein 10 H 167, 10 IV 441.]

4-Cyanophenol(767-00-0)Related Product Information

• 4'-Hydroxyacetophenone
• 4-Nitrobenzonitrile
• Glycolic acid
• 4-Methoxyphenol
• 4-Hydroxybenzamide
• Hydroxy silicone oil
• 4-Hydroxybenzaldehyde
• 4-Hydroxybenzoic acid
• Hydroxyapatite
• Benzonitrile
• Methylparaben
• 4-Hydrazinobenzoic acid hydrochloride
• 4-Hydrazinylbenzoic acid
• 4-METHOXY-1-NAPHTHONITRILE
• 2,3,4-TRIMETHOXYBENZONITRILE
• 2,4,6-Trimethoxybenzonitrile
• 4-Hydroxy-3-methoxybenzonitrile
• 2,4-Dimethoxybenzonitrile