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4-Hydroxybenzonitril
4-HYDROXYBENZONITRILE · 4-HYDROXYBENZOHYDRAZIDE · P-CYANOPHENOL · Hydroxybenzonitrile · Benzonitrile, 4-hydroxy- · PARA-CYANOPHENOL · PHBN · P-nitrile
Identifikatoren & physikalische Daten
| CAS No. | 767-00-0 |
|---|---|
| Summenformel | C7H5NO |
| Durchschnittliche Molmasse | 119,12 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | 4-Hydroxybenzonitril |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 44 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 127 |
| Dampfdruck | 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] |
| Schmelzpunkt | 110-113 °C(lit.) |
| Siedepunkt | 146 °C / 2mmHg |
| Dichte | 1.1871 (rough estimate) |
| Brechungsindex | 1.5800 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | methanol: 0.1 g/mL, clearslightly soluble |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | 7.97(at 25℃) |
| Farbe | Off-white to beige-gray |
| BRN | 386130 |
| Henry-Konstante | 1.4×104 mol/(m3Pa) at 25℃, Hilal et al. (2008) |
| Stabilität | 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 Datenbank | 767-00-0(CAS DataBase Reference) |
| NIST chemische Informationen | 4-Hydroxybenzoic acid nitrile(767-00-0) |
| EPA chemische Informationen | Benzonitrile, 4-hydroxy- (767-00-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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. |
|---|---|
| Regulatorische Informationen | 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 |
| Gefahrenübersicht | 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%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29269095 |
| RTECS-Nr. | DI4375000 |
| R-Sätze (R) | 22-36/37/38 |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
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.