Basic information
- Standard SMILES
N#Cc1ccc(O)cc1- InChIKey
CVNOWLNNPYYEOH-UHFFFAOYSA-N- Molecular formula
- C7H5NO
- Average molar mass
- 119.12 g/mol
- Monoisotopic mass
- 119.03711378
Names & identifiers
- Preferred name
- 4-Cyanophenol
- IUPAC
- 4-hydroxybenzonitrile
- English name
- 4-Cyanophenol
- Molecular formula
- C7H5NO
- Molecular weight
- 119.12
Names & synonyms
4-Hydroxybenzonitrile4-Cyanophenol767-00-0p-HydroxybenzonitrileP-CYANOPHENOLBenzonitrile, 4-hydroxy-Benzonitrile, p-hydroxy-DTXSID90525094-hydroxycyanobenzene1S13529YJUNSC-400524DTXCID7031082
Show more names
4-HYDROXYBENZOHYDRAZIDEHydroxybenzonitrilePARA-CYANOPHENOLPHBNP-nitrileAKOS 217-25AKOS B004225
CHEBI:38622RefChem:98654212-175-24-CYANO PHENOL4-Hydroxy benzonitrile4-hydroxy-benzonitrile4-Hydroxybenzoic acid nitrileMFCD00002312
Database identifiers
- CAS
767-00-0- PubChem CID
- 13019
- DTXSID
DTXSID9052509- ChEMBL
CHEMBL66381- ChEBI
CHEBI:38622- UNII
- 1S13529YJU
- EC Number
- 212-175-2
- Nikkaji
- J36.035J
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 44 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 127
Experimental & physicochemical properties
Vapor Pressure0.00665 [mmHg]
Physical DescriptionMostly soluble in water (8.98 g/L at 25 deg C); [ChemIDplus] White crystalline chips; [MSDSonline]
Collision Cross Section118.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID9052509]
Physicochemical properties
- Melting point
- 110 · 110-113 °C(lit.)
- Boiling point
- 146 °C · 146 °C / 2mmHg
- Density
- 1.1871 · 1.1871 (rough estimate)
- refractive index
- 1.58 · 1.5800 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 0.1 g/mL, · methanol: 0.1 g/mL, clear
- form
- Crystalline Powder
- pka
- 7.97 · 7.97(at 25℃)
- color
- Off-white to beige-gray
- Water Solubility
- slightly soluble
- BRN
- 386130 · 386130
- Henry's Law Constant
- 1.4 · 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 · 767-00-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 S13529YJU · 1S13529YJU
- NIST Chemistry Reference
- 4 · 4-Hydroxybenzoic acid nitrile(767-00-0)
- EPA Substance Registry System
- 4 · Benzonitrile, 4-hydroxy- (767-00-0)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-36-45-24/25
- WGK Germany
- 3 · 3
- RTECS
- 4375000 · DI4375000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29269095 · 29269095
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (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 exposure; Respiratory 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.
Hazard information
Regulatory Information
Chemical: Benzonitrile, 4-hydroxy-
Status: Active Update: 24-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18169
4-Hydroxybenzonitrile: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and eye irritant; [eChemPortal: ERMA] An irritant; [MSDSonline] See NITRILES.
Hazard Classes and CategoriesAcute Tox. 4 (96.8%)；Skin Irrit. 2 (96.8%)；Eye Irrit. 2 (96.8%)；STOT SE 3 (95.2%)
Regulatory information
Regulatory Information
Chemical: Benzonitrile, 4-hydroxy-
Status: Active Update: 24-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18169
4-Hydroxybenzonitrile: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DI4375000
- hs_code
- 29269095
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36-45-24/25
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
UsesUsed in the production of herbicides; [Ullmann]
General Manufacturing InformationBenzonitrile, 4-hydroxy-: ACTIVE
Applications
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.
Preparation methods
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.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
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.
Related reactions
516 records
Linked notes
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