N-(5-Hexynyl)phthalimide

Base Information

• Chemical Name: N-(5-Hexynyl)phthalimide
• CAS No.: 6097-08-1
• Molecular Formula: C14H13NO2
• Molecular Weight: 227.263
• DSSTox Substance ID: DTXSID80391665
• Nikkaji Number: J2.186.065D
• Wikidata: Q82189293
• Mol file: 6097-08-1.mol

Synonyms:6097-08-1;2-(hex-5-yn-1-yl)isoindoline-1,3-dione;N-(5-Hexynyl)phthalimide;6-Phthalimido-1-hexyne;2-hex-5-ynylisoindole-1,3-dione;2-(hex-5-ynyl)isoindoline-1,3-dione;N-5-hexynylphthalimide;N-5-hexynyl phthalimide;6-Phthalimidyl-1-hexyne;N-(5-hexynyl) phthalimide;1H-Isoindole-1,3(2H)-dione, 2-(5-hexynyl)-;SCHEMBL504643;DTXSID80391665;WALVSJIWVWDFCU-UHFFFAOYSA-N;MFCD00671372;N-(5-Hexynyl)phthalimide, >=95%;AKOS015898135;SB64807;AS-63685;CS-0036692;FT-0738025;W11375;2-(hex-5-yn-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione

Chemical Property of N-(5-Hexynyl)phthalimide

Chemical Property:

• Vapor Pressure: 2.25E-05mmHg at 25°C
• Melting Point: 68-72 °C(lit.)
• Refractive Index: 1.581
• Boiling Point: 360.2°C at 760 mmHg
• PKA: -2.14±0.20(Predicted)
• Flash Point: 157°C
• PSA: 37.38000
• Density: 1.196g/cm³
• LogP: 2.02400
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 227.094628657
• Heavy Atom Count: 17
• Complexity: 342

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-(Hex-5-yn-1-yl)isoindoline-1,3-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C#CCCCCN1C(=O)C2=CC=CC=C2C1=O
• Uses: 6-amino-1-hexyne was prepared from N-(5-Hexynyl)phthalimide which is the starting material. Used in the synthesis of Amino-alkyne. Reactant for:TBAF-catalyzed monoreductionRuthenium-catalyzed hydrative conjugative addition to alkenesRegioselective nickel-catalyzed carbocyanation reactionsZinc-catalyzed intermolecular hydroaminationsCopper catalyzed cycloaddition with azides

Technology Process of N-(5-Hexynyl)phthalimide

There total 6 articles about N-(5-Hexynyl)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: 99.0%

phthalimide (136918-14-4,85-41-6) + 5-hexyl-1-ol (928-90-5) → 2-(hex-5-yn-1-yl)isoindole-1,3-dione (6097-08-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.202011996

Reference yield: 86.0%

6-bromo-1-hexyne (66977-99-9) + potassium phtalimide (1074-82-4) → 2-(hex-5-yn-1-yl)isoindole-1,3-dione (6097-08-1)

Guidance literature:

In N,N-dimethyl-formamide; at 90 ℃; for 16h;

DOI:10.1021/acs.orglett.7b00375

Reference yield: 85.0%

1-chloro-5-hexyne (10297-06-0) + potassium phtalimide (1074-82-4) → 2-(hex-5-yn-1-yl)isoindole-1,3-dione (6097-08-1)

Guidance literature:

In N,N-dimethyl-formamide; at 70 ℃; for 16h;

DOI:10.1002/anie.200601090

upstream raw materials:

1-chloro-5-hexyne

potassium phtalimide

5-hexyl-1-ol

phthalimide

Downstream raw materials:

hex-5-yn-1-amine monohydrochloride

C₂₈H₃₆BNO₄Si

Refernces

• 1、 Huang, Huan-Ming,Bellotti, Peter,Daniliuc, Constantin G.,Glorius, Frank. "Radical Carbonyl Propargylation by Dual Catalysis". supporting information. p. 2464 - 2471. Retrieved 2020/12/07.
• 2、 Zelenay, Benjamin,Munton, Peter,Tian, Xiaojie,Díez-González, Silvia. "A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions". supporting information. p. 4725 - 4730. Retrieved 2019/08/01.