3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-methylpropanenitrile

Base Information

• Chemical Name: 3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-methylpropanenitrile
• CAS No.: 92932-15-5
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.224
• DSSTox Substance ID: DTXSID40452165
• Nikkaji Number: J134.959G
• Mol file: 92932-15-5.mol

Synonyms:92932-15-5;3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-methylpropanenitrile;3-(1,3-dioxoisoindol-2-yl)-2-methylpropanenitrile;MFCD11551281;SCHEMBL8861404;DTXSID40452165;AKOS009029290;3-(1,3-Dioxoisoindolin-2-yl)-2-methylpropanenitrile

Chemical Property of 3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-methylpropanenitrile

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 214.074227566
• Heavy Atom Count: 16
• Complexity: 345

Purity/Quality:

3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-methylpropanenitrile 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CN1C(=O)C2=CC=CC=C2C1=O)C#N

Technology Process of 3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-methylpropanenitrile

There total 5 articles about 3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-methylpropanenitrile 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%

2-(2'-cyanoprop-2'-enyl)-1H-isoindole-1,3(2H)-dione (117903-81-8) → 2-(2'-cyanopropyl)-1H-isoindole-1,3(2H)-dione (92932-15-5)

Guidance literature:

With hydrogen; Lindlar's catalyst; In ethyl acetate; at 70 ℃; for 16h; under 7498.65 Torr;

DOI:10.1016/S0957-4166(01)00097-0

Reference yield: 90.0%

phthalimide (136918-14-4,85-41-6) + methacrylonitrile (126-98-7,25067-61-2) → 2-(2'-cyanopropyl)-1H-isoindole-1,3(2H)-dione (92932-15-5)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In methanol; N,N-dimethyl-formamide; at 120 ℃; for 48h;

DOI:10.1002/ardp.19843170908

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;

upstream raw materials:

phthalimide

methacrylonitrile

N-propargylphthalimide

hydrogen cyanide

Downstream raw materials:

(2R)-N-benzyloxycarbonyl-2-aminopropanecarboxylic acid

(RS)-2-(aminomethyl)propanoic acid hydrochloride

Refernces

• 1、 Saylik, Dilek,Campi, Eva M.,Donohue, Andrew C.,Jackson,Robinson, Andrea J.. "A new enantioselective synthesis of β-amino acids". . p. 657 - 667. Retrieved 2007/10/03.
• 2、 Jackson, W. Roy,Perlmutter, Patrick,Smallridge, Andrew. "THE HYDROCYANATION ROUTE TO β- AND γ-AMINO ACIDS. A SYNTHESIS OF α-METHYLENE-β-ALANINE". . p. 1983 - 1984. Retrieved 2007/10/02.