Basic information
- Standard SMILES
N#Cc1ccccc1O- InChIKey
CHZCERSEMVWNHL-UHFFFAOYSA-N- Molecular formula
- C7H5NO
- Average molar mass
- 119.12 g/mol
- Monoisotopic mass
- 119.03711378
Names & identifiers
- Preferred name
- 2-Hydroxybenzonitrile
- IUPAC
- 2-hydroxybenzonitrile
- English name
- 2-Cyanophenol
- Molecular formula
- C7H5NO
- Molecular weight
- 119.12
Names & synonyms
2-Hydroxybenzonitrile2-Cyanophenol611-20-1Salicylonitrileo-Cyanophenolo-HydroxybenzonitrileBenzonitrile, 2-hydroxy-DTXSID304166151RSM8K1VZNSC-53558DTXCID1021661RefChem:473406
Show more names
2-hydroxy-benzonitrilCYANOPHENOLTIMTEC-BB SBB0079592-Cyanopheno2 /4 CyanoPhenol
210-259-3SalicylnitrileBenzonitrile, hydroxy-Benzonitrile, o-hydroxy-o-HydoxybenzonitrileMFCD00002145Hydroxybenzonitrile2-Hydroxy-benzonitrile
Database identifiers
- CAS
611-20-1、69481-42-1- PubChem CID
- 11907
- DTXSID
DTXSID3041661- ChEMBL
CHEMBL195342- ChEBI
CHEBI:194657- UNII
- 51RSM8K1VZ
- EC Number
- 210-259-3
- Nikkaji
- J75B
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
- 135
Experimental & physicochemical properties
Ionization Efficiency
Positive
1.29
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Physicochemical properties
- Melting point
- 92 · 92-95 °C (lit.)
- Boiling point
- 149 °C/14 · 149 °C/14 mmHg (lit.)
- Density
- 1.1052 · 1.1052
- vapor pressure
- 0.17 Pa · 0.17Pa at 25℃
- refractive index
- 1.5372 · 1.5372
- Flash point
- 149 °C/14mm · 149°C/14mm
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Chloroform (Sparingly), Methanol (Slightly)
- form
- Crystalline Powder
- pka
- 6.86 · 6.86(at 25℃)
- color
- Off-white to brown
- Water Solubility
- soluble
- BRN
- 1210029 · 1210029
- Henry's Law Constant
- 2.8 · 2.8×101 mol/(m3Pa) at 25℃, Hilal et al. (2008)
- Stability
- Stable. Incompatible with strong oxidizing agents, strong bases.
- InChI
- 1S/C7H5NO/c8-5-6-3-1-2-4-7(6)9/h1-4,9H
- InChIKey
- CHZCERSEMVWNHL-UHFFFAOYSA-N
- SMILES
- Oc1ccccc1C#N
- LogP
- 1.66 at · 1.66 at 30℃
- CAS DataBase Reference
- 611 · 611-20-1(CAS DataBase Reference)
- FDA UNII
- 51 RSM8K1VZ · 51RSM8K1VZ
- NIST Chemistry Reference
- 2 · Benzonitrile, 2-hydroxy-(611-20-1)
- EPA Substance Registry System
- 2 · Benzonitrile, 2-hydroxy- (611-20-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H317-H318
- Precautionary statements
- 280 · P280-P301+P312+P330-P305+P351+P338+P310
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38-20/21/22
- Safety Statements
- 26 · 26-36-45
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29269095 · 29269095
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Skin Sens. 1B
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (99.2%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (38.3%): Causes skin irritation [Warning Skin corrosion/irritation]；H317 (61.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]；H318 (60%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H319 (38.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (37.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 120 reports by companies from 11 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, 2-hydroxy-
Status: Active Update: 30-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5252
2-Hydroxybenzonitrile: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (99.2%)；Skin Irrit. 2 (38.3%)；Skin Sens. 1 (61.7%)；Eye Dam. 1 (60%)；Eye Irrit. 2 (38.3%)；STOT SE 3 (37.5%)
Regulatory information
Regulatory Information
Chemical: Benzonitrile, 2-hydroxy-
Status: Active Update: 30-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5252
2-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, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29269095
- risk_code
- 22-36/37/38-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36-45
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H317-H318
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Sens. 1B
- Precautionary statements
- P280-P301+P312+P330-P305+P351+P338+P310
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzonitrile, 2-hydroxy-: ACTIVE
Applications
DescriptionCyanophenol is a vital molecule widely used to synthesize liquid crystal materials, medicines, spices, pesticides, corrosion inhibitors, etc. Cyanophenol is formed by substituting two hydrogen atoms of benzene molecules with hydroxyl and cyano groups, respectively. The cyano and hydroxyl groups are in the ring plane in the stable molecular structure. The hydroxyl group can have two different orientations relative to the cyano group. 2-cyanophenol, one of the Cyanophenol, is an essential ingredient in pesticides, spices, liquid crystal materials, etc. It is an especially critical intermediate for synthesizing methoxyacrylate fungicide mystrostrobin, widely used in agrochemicals, pharmaceutical chemicals, and other industries. The cyano group can strongly attract electrons. Replacing a hydrogen atom of the benzene ring by the cyano group usually increases the ionization energy (IE)[1].
Uses2-Hydroxybenzonitrile is used as starting reagent during the synthesis of mono-alkoxyphenyloxazoline, furanoside.
Preparation methods
PreparationA method for preparing 2-cyanophenol, which comprises the following steps: preparing salicylaldoxime; performing dehydration; and performing hydrolytic-acidification reaction, wherein in the dehydration, anhydride is adopted as a dehydrating agent; and in the hydrolytic-acidification reaction, a hydrolyticreagent is 10 to 30 mass percent alkaline solution, and the temperature of the hydrolytic-acidification reaction is 100 to 150℃.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 2-Cyanophenol is a member of benzenes and a nitrile.
Related reactions
194 records
Linked notes
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