Benzenamine, N-ethyl-N-2-propynyl-

Base Information

• Chemical Name: Benzenamine, N-ethyl-N-2-propynyl-
• CAS No.: 18158-72-0
• Molecular Formula: C11H13N
• Molecular Weight: 159.231
• DSSTox Substance ID: DTXSID20394993
• Wikidata: Q82194739
• Mol file: 18158-72-0.mol

Synonyms:Benzenamine, N-ethyl-N-2-propynyl-;18158-72-0;N-ethyl-N-propargylaniline;SCHEMBL333318;DTXSID20394993;RCBNAOAYBZFSEC-UHFFFAOYSA-N;AKOS009058596

Chemical Property of Benzenamine, N-ethyl-N-2-propynyl-

Chemical Property:

• Boiling Point: 119-120 °C(Press: 15 Torr)
• PSA: 3.24000
• Density: 0.9922 g/cm3
• LogP: 2.14610
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 159.104799419
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC#C)C1=CC=CC=C1

Technology Process of Benzenamine, N-ethyl-N-2-propynyl-

There total 7 articles about Benzenamine, N-ethyl-N-2-propynyl- 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: 95.0%

N-phenyl-N-prop-2-ynylamine (14465-74-8) + ethyl iodide (75-03-6) → N-ethyl-N-phenyl-N-propargylamine (18158-72-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol501618z

Reference yield: 82.0%

diethylzinc (557-20-0) + nitrobenzene (98-95-3,26969-40-4) + propargyl bromide (106-96-7) → N-ethyl-N-phenyl-N-propargylamine (18158-72-0)

Guidance literature:

diethylzinc; nitrobenzene; With triethylamine; bis(pinacol)diborane; In hexane; toluene; at 20 ℃; for 12h; Schlenk technique; Inert atmosphere;

propargyl bromide; In hexane; toluene; at 20 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201705356

Reference yield: 61.0%

N-ethyl-N-phenylamine (103-69-5) + propargyl bromide (106-96-7) → N-ethyl-N-phenyl-N-propargylamine (18158-72-0)

Guidance literature:

for 4h; Heating;

upstream raw materials:

N-ethyl-N-phenylamine

propargyl bromide

N-ethyl-N-(2-bromo-allyl)-aniline

N-allyl-N-ethylaniline

Downstream raw materials:

N-ethyl-N-phenyl-N-(3-ethoxy-2-phenylsulphinylpropyl)amine

N-ethyl-N-phenyl-N-(3-phenylthio-2-phenylsulphinylpropyl)amine

(Z)-N-ethyl-N-phenyl-N-(3-ethoxyprop-2-enyl)amine

(E)-N-ethyl-N-phenyl-N-(3-ethoxyprop-2-enyl)amine

Refernces

• 1、 Rauser, Marian,Ascheberg, Christoph,Niggemann, Meike. "Electrophilic Amination with Nitroarenes". supporting information. p. 11570 - 11574. Retrieved 2017/09/11.
• 2、 Rajagopal, Basker,Chou, Chih-Hung,Chung, Ching-Cheng,Lin, Po-Chiao. "Synthesis of substituted 3-indolylimines and indole-3-carboxaldehydes by rhodium(II)-catalyzed annulation". supporting information. p. 3752 - 3755. Retrieved 2014/08/05.