N-[3-(Trimethylsilyl)-2-propynyl]phthalimide

Base Information

• Chemical Name: N-[3-(Trimethylsilyl)-2-propynyl]phthalimide
• CAS No.: 351029-12-4
• Molecular Formula: C₁₄H₁₅NO₂Si
• Molecular Weight: 257.364
• European Community (EC) Number: 622-233-2
• DSSTox Substance ID: DTXSID60478246
• Wikidata: Q82311485
• Mol file: 351029-12-4.mol

Synonyms:N-[3-(Trimethylsilyl)-2-propynyl]phthalimide;351029-12-4;2-(3-trimethylsilylprop-2-ynyl)isoindole-1,3-dione;2-(3-(Trimethylsilyl)prop-2-yn-1-yl)isoindoline-1,3-dione;1-Phthalimido-3-(trimethylsilyl)propyne;starbld0033463;DTXSID60478246;N-(3-(TRIMETHYLSILYL-2-PROPYNYL)PHTHAL;J-019938;N-[3-(Trimethylsilyl)-2-propynyl]phthalimide, 97%

Chemical Property of N-[3-(Trimethylsilyl)-2-propynyl]phthalimide

Chemical Property:

• Melting Point: 131-136 °C
• PSA: 37.38000
• LogP: 2.10130
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 257.087205256
• Heavy Atom Count: 18
• Complexity: 414

Purity/Quality:

97% ^*data from raw suppliers

N-[3-(Trimethylsilyl)-2-propynyl]phthalimide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CCN1C(=O)C2=CC=CC=C2C1=O

Technology Process of N-[3-(Trimethylsilyl)-2-propynyl]phthalimide

There total 2 articles about N-[3-(Trimethylsilyl)-2-propynyl]phthalimide 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: 90.0%

3-bromo-1-(trimethylsilyl)-1-propyne (38002-45-8) + potassium phtalimide (1074-82-4) → N-[3'-(trimethylsilyl)prop-2'-ynyl]phthalimide (351029-12-4)

Guidance literature:

With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmcl.2009.09.011

Reference yield: 43.0%

phthalimide (136918-14-4,85-41-6) + 3-trimethylsilyl-2-propyn-1-ol (5272-36-6) → N-[3'-(trimethylsilyl)prop-2'-ynyl]phthalimide (351029-12-4)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201707933

Reference yield:

C13H17N (1016970-52-7) + N-[3'-(trimethylsilyl)prop-2'-ynyl]phthalimide (351029-12-4) → C24H26N2O2

Guidance literature:

Multi-step reaction with 2 steps

1: chlorobis(cyclooctene)rhodium(I) dimer; diethyl-{4-dimethylamino-phenyl}-phosphine / toluene / 1 h / 100 °C / Inert atmosphere

2: diphenyl hydrogen phosphate; tetramethylammonium triacetoxyborohydride / dichloromethane / 20 °C / Inert atmosphere

With diphenyl hydrogen phosphate; chlorobis(cyclooctene)rhodium(I) dimer; diethyl-{4-dimethylamino-phenyl}-phosphine; tetramethylammonium triacetoxyborohydride; In dichloromethane; toluene;

DOI:10.1021/ja312311k

upstream raw materials:

3-bromo-1-(trimethylsilyl)-1-propyne

potassium phtalimide

phthalimide

3-trimethylsilyl-2-propyn-1-ol

Refernces

• 1、 Bernard, Sylvain,Defoy, Daniel,Dory, Yves L.,Klarskov, Klaus. "Efficient synthesis of nevirapine analogs to study its metabolic profile by click fishing". supporting information; experimental part. p. 6127 - 6130. Retrieved 2010/06/13.