CAS 115-46-8 Azacyclonol (HCID 15723)

Overview

Diphenyl(4-piperidinyl)methanol is a diarylmethane.

Names & identifiers

Preferred name: Azacyclonol
IUPAC: diphenyl(piperidin-4-yl)methanol
English name: alpha,alpha-Diphenyl-4-piperidinomethanol
Molecular formula: C18H21NO
Molecular weight: 267.37

Names & synonyms

Azacyclonol115-46-8diphenyl(piperidin-4-yl)methanolgamma-PipradolAzaciclonoloAzacyclonolumazaciclonolDTXSID20452802MMR990PEMDTXCID0025280RefChem:115914204-092-5

Show more names

Azacyclanolalpha,alpha-diphenyl-4-piperidinemethanomer17MER 17FrenquelFrenotonMDL 4829

alpha,alpha-diphenyl-4-piperidinomethanolalpha-(4-Piperidyl)benzhydrolDiphenyl(4-piperidinyl)methanol4-Piperidinemethanol, alpha,alpha-diphenyl-alpha,alpha-Diphenyl-4-piperidinemethanolAtaractanCalmeranPsychosan

Database identifiers

CAS: 115-46-8
PubChem CID: 15723
DTXSID: DTXSID2045280
ChEMBL: CHEMBL127508
ChEBI: CHEBI:93706
UNII: 2MMR990PEM
EC Number: 204-092-5
Nikkaji: J5.268J

Properties

Computed structural properties

XLogP: 2.9
Topological polar surface area: 32.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 20
Formal charge: 0
Complexity: 268

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals -> Metabolite of Fexofenadine

Solubility>40.1 [ug/mL] (The mean of the results at pH 7.4)

Collision Cross Section159.3 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 160 · 160-163 °C
Boiling point: 410.55 °C · 410.55°C (rough estimate)
Density: 1.0449 · 1.0449 (rough estimate)
vapor pressure: 0 Pa · 0Pa at 25℃
refractive index: 1.51 · 1.5100 (estimate)
storage temp.: 30 °C · Store below +30°C.
solubility: Chloroform, Methanol (Slightly, Sonicated)
pka: 13.32 · 13.32±0.29(Predicted)
form: Solid
color: White to light beige
InChI: InChI=1S/C18H21NO/c20-18(15-7-3-1-4-8-15,16-9-5-2-6-10-16)17-11-13-19-14-12-17/h1-10,17,19-20H,11-14H2
InChIKey: ZMISODWVFHHWNR-UHFFFAOYSA-N
SMILES: C(O)(C1CCNCC1)(C1=CC=CC=C1)C1=CC=CC=C1
CAS DataBase Reference: 115 · 115-46-8(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 2 MMR990PEM · 2MMR990PEM
NIST Chemistry Reference: Azacyclonol(115-46-8)
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H319
Precautionary statements: 264 · P264-P270-P280-P301+P312-P305+P351+P338-P337+P313
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 24 · 24/25
WGK Germany: 3 highly · WGK 3 highly water endangering
RTECS: 470000 · TN0470000
HS Code: 29333999 · 29333999
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 17 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 09-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5946

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

wgk: WGK 3 highly water endangering
rtecs: TN0470000
hs_code: 29333999
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H319
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2
Precautionary statements: P264-P270-P280-P301+P312-P305+P351+P338-P337+P313

Chemistry & industry

Pharmacology

Metabolism/MetabolitesAzacyclonol is a known human metabolite of terfenadine.

Applications · 3 items

Descriptionalpha,alpha-Diphenyl-4-piperidinomethanol is an important organic synthetic substance for the synthesis of diphenyl-4-piperidinomethanol. It is also used as a pharmaceutical intermediate in the preparation of terfenadine and Fexofenadine hydrochloride.

UsesAnxiolytic;H1 antagonist

Usesα-(4-Piperidyl)benzhydrol is a key intermediate in the synthesis of Fexofenadine (F322490). Fexofenadine EP Impurity E.

Preparation methods · 1 item

PreparationUsing 4-piperidinic acid as a starting material, N-ethoxycarbonyl-4-piperidinic acid methyl ester was prepared by reacting it with ethyl chloroformate in a one-pot reaction involving esterification and amino protection. This methyl ester was then reacted with magnesium phenyl bromide to prepare N-ethoxycarbonyl-α,α-diphenyl-4-piperidinol, which was finally hydrolyzed with potassium hydroxide to obtain the target compound. This process utilizes inexpensive and readily available raw materials, has a short synthetic route, is simple to operate, and achieves an overall yield of 68.8%.