Thiofentanyl

Base Information

• Chemical Name: Thiofentanyl
• CAS No.: 1165-22-6
• Molecular Formula: C20H26 N2 O S
• Molecular Weight: 342.5
• NSC Number: 665714
• UNII: 954535Y32Y
• DSSTox Substance ID: DTXSID00151400
• Nikkaji Number: J92.621C
• Wikipedia: Thiofentanyl
• Wikidata: Q7784665
• Metabolomics Workbench ID: 61457
• ChEMBL ID: CHEMBL1997223
• Mol file: 1165-22-6.mol

Synonyms:Thiofentanyl;thienylfentanil;Thienylfentanyl;1165-22-6;N-(1-(beta-(2-Thienyl)ethyl)-4-piperidyl)propioanilide;CHEBI:61099;N-Phenyl-N-(1-((2-thienyl)ethyl)-4-piperidinyl)propanamide;NSC665714;BRN 0495808;DEA No. 9835;UNII-954535Y32Y;NSC 665714;NSC-665714;Propionanilide, N-(1-(2-(2-thienyl)ethyl)-4-piperidyl)-;954535Y32Y;5-22-08-00089 (Beilstein Handbook Reference);C20H26N2OS;1-[2-(2-Thienyl)ethyl]-4-(N-propionylanilino)piperidine;N-phenyl-N-{1-[2-(2-thienyl)ethyl]piperidin-4-yl}propanamide;NCGC00247697-01;Thiofentany;N-PHENYL-N-(1-(2-(2-THIENYL)ETHYL)PIPERIDIN-4-YL)PROPANAMIDE;Epitope ID:153514;SCHEMBL614459;IDS-NT-005;CHEMBL1997223;DTXSID00151400;IDS-NT-005(SECT.3);N-Phenyl-N-(1-(2-(2-thienyl)ethyl)-4-piperidinyl)propanamide;N-phenyl-N-[1-(2-thiophen-2-ylethyl)piperidin-4-yl]propanamide;DB09180;NCI60_022700;LS-124457;Q7784665;N-(1-(2-(THIENYL)ETHYL)-4-PIPERIDYL)PROPIONANILIDE;N-phenyl-N-[1-[2-(2-thienyl)ethyl]-4-piperidyl]propanamide;PROPANAMIDE, N-PHENYL-N-(1-(2-(2-THIENYL)ETHYL)-4-PIPERIDINYL)-

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Chemical Property of Thiofentanyl

Chemical Property:

• Vapor Pressure: 6.36E-09mmHg at 25°C
• Boiling Point: 467.7°C at 760 mmHg
• Flash Point: 236.7°C
• PSA: 51.79000
• Density: 1.145g/cm³
• LogP: 4.13610
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 342.17658463
• Heavy Atom Count: 24
• Complexity: 389

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)N(C1CCN(CC1)CCC2=CC=CS2)C3=CC=CC=C3

Technology Process of Thiofentanyl

There total 6 articles about Thiofentanyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

N-phenyl-1-(2-(thiophen-2-yl)ethyl)piperidine-4-amine + propionyl chloride (79-03-8) → thiofentanyl (1165-22-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1371/journal.pone.0108250

Reference yield:

aniline (62-53-3) → thiofentanyl (1165-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 14 h / 20 °C / Cooling with ice

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C

With sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1371/journal.pone.0108250

Reference yield:

N-[2-(2-thienyl)ethyl]-4-piperidinone (92065-14-0) → thiofentanyl (1165-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 14 h / 20 °C / Cooling with ice

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C

With sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1371/journal.pone.0108250

upstream raw materials:

aniline

propionyl chloride

2-(thiophen-2-yl)ethyl methanesulfonate

2-thiophenethanol

Downstream raw materials:

N-Phenyl-N-<1-<2-(2-thienyl)ethyl>-4-piperidyl>propanamide Hydrochloride

Refernces

• 1、 Valdez, Carlos A.,Leif, Roald N.,Mayer, Brian P.. "An efficient, optimized synthesis of fentanyl and related analogs". . . Retrieved 2015/02/19.