4-Phthalimidobutyronitrile

Base Information

• Chemical Name: 4-Phthalimidobutyronitrile
• CAS No.: 3184-61-0
• Molecular Formula: C12H10 N2 O2
• Molecular Weight: 214.224
• Hs Code.: 2926909090
• NSC Number: 92793
• DSSTox Substance ID: DTXSID90293888
• Nikkaji Number: J1.530.553C
• Wikidata: Q82032884
• Mol file: 3184-61-0.mol

Synonyms:3184-61-0;4-Phthalimidobutyronitrile;4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butanenitrile;4-(1,3-dioxoisoindol-2-yl)butanenitrile;4-(1,3-Dioxoisoindolin-2-yl)butanenitrile;4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)butanenitrile;NSC92793;N-(3-Cyanopropyl)phthalimide;SCHEMBL5889451;DTXSID90293888;MFCD00797314;NSC-92793;STL262626;AKOS000195812;SB64825;LS-06120;4-(1,3-dioxo-isoindol-2-yl)-butyronitrile;CS-0206843;FT-0651624;EN300-217025;A821023;Z54769061;4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyronitrile;4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butanenitrile #

Chemical Property of 4-Phthalimidobutyronitrile

Chemical Property:

• Vapor Pressure: 9.83E-07mmHg at 25°C
• Boiling Point: 403.9°Cat760mmHg
• Flash Point: 198.1°C
• PSA: 61.17000
• Density: 1.286g/cm³
• LogP: 1.52428
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 214.074227566
• Heavy Atom Count: 16
• Complexity: 331

Purity/Quality:

98%min ^*data from raw suppliers

4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CCCC#N

Technology Process of 4-Phthalimidobutyronitrile

There total 3 articles about 4-Phthalimidobutyronitrile 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: 42.0%

2-(5-(4-methoxyphenyl)pent-4-yn-1-yl)isoindoline-1,3-dione (1435331-50-2) → 4-phthalimidobutyronitrile (3184-61-0) + 4-methoxybenzonitrile (874-90-8)

Guidance literature:

With N-iodo-succinimide; trimethylsilylazide; In 1,2-dichloro-ethane; acetonitrile; at 20 - 70 ℃; for 3h;

DOI:10.1021/ol401311h

Reference yield: 17.0%

→ 4-phthalimidobutyronitrile (3184-61-0) + 2-(2'-cyanopropyl)-1H-isoindole-1,3(2H)-dione (92932-15-5)

Guidance literature:

With dmap; 1,3-bis-(diphenylphosphino)propane; Ni(ClO₄)2*6H₂O; zinc; In water; acetonitrile; at 80 ℃; for 24h; Glovebox; Inert atmosphere;

Reference yield:

N-(pent-4-ynyl)phthalimide (6097-07-0) + para-iodoanisole (696-62-8) → 4-phthalimidobutyronitrile (3184-61-0) + 4-methoxybenzonitrile (874-90-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; palladium diacetate; triphenylphosphine; copper(l) iodide / 20 °C / Inert atmosphere

2: N-iodo-succinimide; trimethylsilylazide / 1,2-dichloro-ethane; acetonitrile / 3 h / 20 - 70 °C

With N-iodo-succinimide; copper(l) iodide; trimethylsilylazide; palladium diacetate; triethylamine; triphenylphosphine; In 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/ol401311h

upstream raw materials:

2-(5-(4-methoxyphenyl)pent-4-yn-1-yl)isoindoline-1,3-dione

N-(pent-4-ynyl)phthalimide

para-iodoanisole

Downstream raw materials:

N-<4-butyl>phthalimide

N-<(4-(N-nitroso-p-toluenesulfonamido)-1-butyl)>phthalimide

N-(4-hydroxy-1-butyl)phthalimide tosylate

N-(4-benzamido-1-butyl)phthalimide

Refernces

• 1、 Okamoto, Noriko,Ishikura, Minoru,Yanada, Reiko. "Cleavage of carbon-carbon triple bond: Direct transformation of alkynes to nitriles". supporting information. p. 2571 - 2573. Retrieved 2013/07/11.