CAS 52927-22-7 6-Hydroxy-2-naphthonitrile (HCID 4589476)

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Basic information

CAS: 52927-22-7
Standard SMILES: N#Cc1ccc2cc(O)ccc2c1
InChIKey: WKTNIBWKHNIPQR-UHFFFAOYSA-N
Molecular formula: C11H7NO
Average molar mass: 169.18 g/mol
Monoisotopic mass: 169.05276384

Names & identifiers

Preferred name: 6-Hydroxy-2-naphthonitrile
IUPAC: 6-hydroxynaphthalene-2-carbonitrile
English name: 6-Cyano-2-naphthol
Molecular formula: C11H7NO
Molecular weight: 169.18

Names & synonyms

6-Hydroxy-2-naphthonitrileRefChem:543376628-663-76-Cyano-2-naphthol52927-22-76-hydroxynaphthalene-2-carbonitrile2-Naphthalenecarbonitrile, 6-hydroxy-MFCD018634806-Hydroxy-naphthalene-2-carbonitrile6-hydroxy-2-naphthalenecarbonitrile2-hydroxy-6-cyanonaphthaleneSCHEMBL1028464

Show more names

CYANO(6-)-2-NAPTHOL6-CYANO-2-NAPHTHALENOL6-CYANO-2-NAPHTHOL 99%Nafamostat Impurity 22Nafamostat Impurity 256-Cyano-2-naphthol ,99%Crisaborole Impurity 87

AC-6788SY021503H0995EN300-16151222-Cyano-6-naphthol2-Cyano-6-hydroxynaphthaleneAM87038A7718

Database identifiers

CAS: 52927-22-7
PubChem CID: 4589476
DTXSID: DTXSID90404614
EC Number: 628-663-7
Nikkaji: J633.569A

Properties

Computed structural properties

XLogP: 2.4
Topological polar surface area: 44 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 13
Formal charge: 0
Complexity: 229

Physicochemical properties

Melting point: 165.5 · 165.5-170.5 °C (lit.)
Boiling point: 383.1 · 383.1±15.0 °C(Predicted)
Density: 1.28 · 1.28±0.1 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: DMSO (Slightly), Ethanol, Ethyl Acetate (Slightly), Methanol (Slightly)
form: Solid
pka: 8.57 · 8.57±0.40(Predicted)
color: Pale Brown to Brown
InChI: InChI=1S/C11H7NO/c12-7-8-1-2-10-6-11(13)4-3-9(10)5-8/h1-6,13H
InChIKey: WKTNIBWKHNIPQR-UHFFFAOYSA-N
SMILES: C1=C2C(C=C(O)C=C2)=CC=C1C#N
CAS DataBase Reference: 52927 · 52927-22-7(CAS DataBase Reference)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 29269090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 3 items

UsesIntermediate of Nafamostat mesilate (N210000).

UsesReactant for:Palladium-catalyzed reductionNickel-catalyzed cross-coupling reactionsPalladium-catalyzed Heck reactions

General Description6-Cyano-2-naphthol (6CN2) is an aromatic alcohol that can be synthesized from 6-bromo-2-naphthol. It is a superphotoacid with the ground state pKa* value of 8.4 and excited state pKavalue of 0.2, respectively. 6CN2 protonates PANI-ES (polyaniline emeraldine salt) to form PANI-EB (emeraldine base), which shows enhanced conductivity. The proton-transfer kinetics and photophysical behavior of 6CN2 have been investigated.