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4-Cyanophenol

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4-Cyanophenol Basic information
Product Name:4-Cyanophenol
Synonyms:p-hydroxy benzonitrile,p-cyano phenol;4-HYDROXYBENZONITRILE FOR SYNTHESIS;AKOS B004225;AKOS 217-25;4-CYANOPHENOL;4-HYDROXYBENZONITRILE;CYANOPHENOL(4-);P-CYANOPHENOL
CAS:767-00-0
MF:C7H5NO
MW:119.12
EINECS:212-175-2
Product Categories:Aromatic Nitriles;Phenoles and thiophenoles;Nitriles;Phenols;Benzonitriles (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Benzoic acid Series;Pesticide Intermediate;Liquid Crystal intermediates;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;Alpha sort;H;H-MAlphabetic;HU - HZ;Pesticides&Metabolites;767-00-0;1
Mol File:767-00-0.mol
4-Cyanophenol Structure
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
pka7.97(at 25℃)
color Off-white to beige-gray
Water Solubility slightly soluble
BRN 386130
Stability:Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference767-00-0(CAS DataBase Reference)
NIST Chemistry Reference4-Hydroxybenzoic acid nitrile(767-00-0)
EPA Substance Registry SystemBenzonitrile, 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 Information
ProviderLanguage
4-Hydroxybenzonitrile English
SigmaAldrich English
ACROS English
ALFA English
4-Cyanophenol Usage And Synthesis
Chemical Propertieswhite 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).
UsesIntermediates of Liquid Crystals
Uses4-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.
Preparation4-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.
DefinitionChEBI: 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 MethodsCrystallise 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.]
Tag:4-Cyanophenol(767-00-0) Related Product Information
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