3-Anilino-3-methyl-1-pentyne

Base Information

• Chemical Name: 3-Anilino-3-methyl-1-pentyne
• CAS No.: 14465-46-4
• Molecular Formula: C12H15 N
• Molecular Weight: 173.2542
• DSSTox Substance ID: DTXSID00932372
• Mol file: 14465-46-4.mol

Synonyms:BRN 2803112;3-Anilino-3-methyl-1-pentyne;14465-46-4;ANILINE, N-(3-METHYL-1-PENTYN-3-YL)-;N-(3-methylpent-1-yn-3-yl)aniline;DTXSID00932372;LS-19898

Chemical Property of 3-Anilino-3-methyl-1-pentyne

Chemical Property:

• Vapor Pressure: 0.00398mmHg at 25°C
• Melting Point: 36-37 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 279.6°Cat760mmHg
• PKA: 4.00±0.50(Predicted)
• Flash Point: 124.9°C
• PSA: 12.03000
• Density: 0.988g/cm³
• LogP: 2.97340
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 173.120449483
• Heavy Atom Count: 13
• Complexity: 194

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C#C)NC1=CC=CC=C1

Technology Process of 3-Anilino-3-methyl-1-pentyne

There total 8 articles about 3-Anilino-3-methyl-1-pentyne 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: 98.0%

1-bromo-3-methyl-1,2-pentadiene (10575-70-9) + aniline (62-53-3) → N-(3-methylpent-1-yn-3-yl)aniline (14465-46-4)

Guidance literature:

copper(I) bromide; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1016/0040-4039(91)80138-V

Reference yield: 82.0%

N2-phenyl-2-butanimine (40296-03-5) + acetylene (74-86-2,25067-58-7) → N-(3-methylpent-1-yn-3-yl)aniline (14465-46-4)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 20 - 35 ℃; for 1h; under 1748.12 - 1976.13 Torr;

DOI:10.1002/ejoc.201900932

Reference yield: 65.0%

1-trimethylsilyl-3-methyl-3-chloropent-1-yne (17889-27-9) + aniline (62-53-3) → N-(3-methylpent-1-yn-3-yl)aniline (14465-46-4)

Guidance literature:

With copper bronze; water; copper; triethylamine; copper(l) iodide; In tetrahydrofuran; at 60 - 70 ℃; for 4h;

upstream raw materials:

aniline

3-chloro-3-methylpent-1-yne

1-bromo-3-methyl-1,2-pentadiene

3-acetoxy-3-ethylbutyne

Downstream raw materials:

(1-ethyl-1-methyl-allyl)-phenyl-amine

2-Ethyl-2-methyl-1,2,3,4-tetrahydro-quinolin-7-ylamine

N-(1-ethyl-1-methyl-propyl)-aniline

Refernces

• 1、 Schmidt, Elena Yu.,Bidusenko, Ivan A.,Protsuk, Nadezhda I.,Demyanov, Yan V.,Ushakov, Igor A.,Trofimov, Boris A.. "Superbase-Promoted Addition of Acetylene Gas to the C=N Bond". . p. 5875 - 5881. Retrieved 2019/09/10.
• 2、 Hamann, Lawrence G.,Higuchi, Robert I.,Zhi, Lin,Edwards, James P.,Wang, Xiao-Ning,Marschke, Keith B.,Kong, James W.,Farmer, Luc J.,Jones, Todd K.. "Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2- dihydropyridono[5,6-g]quinolines". . p. 623 - 639. Retrieved 2007/10/03.