HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Cyanophenol
4-HYDROXYBENZONITRILE · 4-HYDROXYBENZOHYDRAZIDE · P-CYANOPHENOL · Hydroxybenzonitrile · Benzonitrile, 4-hydroxy- · PARA-CYANOPHENOL · PHBN · P-nitrile
Identifiers & Physical Properties
| CAS No. | 767-00-0 |
|---|---|
| Molecular formula | C7H5NO |
| Average molar mass | 119.12 g/mol |
| Monoisotopic mass | 119.03711378 g/mol |
| SMILES | N#Cc1ccc(O)cc1 |
| InChIKey | CVNOWLNNPYYEOH-UHFFFAOYSA-N |
| PubChem CID | 13019 |
| ChEMBL | CHEMBL66381 |
| ChEBI | CHEBI:38622 |
| EC No. | 212-175-2 |
| DTXSID | DTXSID9052509 |
Chemical & Physical Properties
| XLogP | 1.6 |
|---|---|
| Topological polar surface area | 44 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 127 |
| Vapor pressure | 0.00665 [mmHg] |
| Physical Description | Mostly soluble in water (8.98 g/L at 25 deg C)[ChemIDplus] White crystalline chips[MSDSonline] |
| Collision Cross Section | 118.1 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID9052509] |
| Melting point | 110-113 °C(lit.) |
| Boiling point | 146 °C / 2mmHg |
| Density | 1.1871 (rough estimate) |
| Refractive index | 1.5800 (estimate) |
| Storage conditions | Inert atmosphere,Room Temperature |
| Solubility | methanol: 0.1 g/mL, clearslightly soluble |
| Physical state | Crystalline Powder |
| pKa (acidity coefficient) | 7.97(at 25℃) |
| Color | Off-white to beige-gray |
| BRN | 386130 |
| Henry's law constant | 1.4×104 mol/(m3Pa) at 25℃, Hilal et al. (2008) |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| InChI | 1S/C7H5NO/c8-5-6-1-3-7(9)4-2-6/h1-4,9H |
| InChIKey | CVNOWLNNPYYEOH-UHFFFAOYSA-N |
| SMILES | Oc1ccc(cc1)C#N |
| CAS DataBase Reference | 767-00-0(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 1S13529YJU |
| NIST Chemistry Reference | 4-Hydroxybenzoic acid nitrile(767-00-0) |
| EPA Substance Registry System | Benzonitrile, 4-hydroxy- (767-00-0) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
| Hazard symbols | Xn,Xi |
| Risk statements (R) | 22-36/37/38 |
| Safety statements (S) | 26-36-45-24/25 |
| Water hazard class (WGK) | 3 |
| RTECS number | DI4375000 |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Customs code | 29269095 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | WarningH302 (96.8%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (96.8%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (96.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (95.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 62 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: Benzonitrile, 4-hydroxy-Status: Active Update: 24-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/181694-Hydroxybenzonitrile: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | A skin and eye irritant[eChemPortal: ERMA] An irritant[MSDSonline] See NITRILES. |
| Hazard Classes and Categories | Acute Tox. 4 (96.8%)Skin Irrit. 2 (96.8%)Eye Irrit. 2 (96.8%)STOT SE 3 (95.2%) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | DI4375000 |
| Customs code | 29269095 |
| Risk statements (R) | 22-36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn,Xi |
| hazard_note | Irritant |
| Safety statements (S) | 26-36-45-24/25 |
| Storage class | 11 - Combustible Solids |
| Target organs | Respiratory system |
| GHS hazard statements | H315-H319-H335 |
| REACH registrations | Active |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
Applications & Uses
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 & Synthesis
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.