5-Methoxyisoindoline

Base Information

• Chemical Name: 5-Methoxyisoindoline
• CAS No.: 127168-88-1
• Molecular Formula: C9H11NO
• Molecular Weight: 149.192
• Hs Code.: 2933990090
• European Community (EC) Number: 831-175-9
• DSSTox Substance ID: DTXSID10564163
• Nikkaji Number: J1.526.245A
• Wikidata: Q72490122
• Mol file: 127168-88-1.mol

Synonyms:5-Methoxyisoindoline;127168-88-1;5-Methoxy-2,3-dihydro-1H-isoindole;1H-ISOINDOLE, 2,3-DIHYDRO-5-METHOXY-;5-methoxylisoindoline;5-methoxyisoindo line;SCHEMBL330398;DTXSID10564163;BNBIUUBEQGUPJK-UHFFFAOYSA-N;MFCD06804552;AKOS006221845;AB30381;CS-W008864;SB32600;AC-27104;AS-38084;2,3-DIHYDRO-5-METHOXY-1H-ISOINDOLE;A2662;EN300-252429;W-205266

Chemical Property of 5-Methoxyisoindoline

Chemical Property:

• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: 1.545
• Boiling Point: 254.14 °C at 760 mmHg
• PKA: 9.56±0.20(Predicted)
• Flash Point: 95.269 °C
• PSA: 21.26000
• Density: 1.076g/cm³
• LogP: 1.62720
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 149.084063974
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

5-Methoxy-2,3-dihydro-1H-isoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(CNC2)C=C1
• Uses: 5-Methoxyisoindoline is a reagent used in the sysnthesis of PDK inhibitors for used in targetting glucose and fat levels in type 2 diabetes. Also used in the preparation of C20’ ureas based on 20’amino-vinblastine for use against vinblastine-resistant cancer cell lines.

Technology Process of 5-Methoxyisoindoline

There total 5 articles about 5-Methoxyisoindoline 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: 47.0%

4-methoxyphthalimide (50727-04-3) → 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1)

Guidance literature:

4-methoxyphthalimide; With borane-THF; In tetrahydrofuran; at 0 ℃; for 16h; Heating / reflux;

With hydrogenchloride; In tetrahydrofuran; methanol; water; for 3h; Heating / reflux;

Reference yield:

N-benzylisoindolin-5-yl methyl ether (127168-89-2) → 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1)

Guidance literature:

With Pd(OH)2/C; ammonium formate; In methanol; Reflux;

DOI:10.1016/j.bmcl.2008.05.069

Reference yield:

5-methoxy-2-[(4-methylphenyl)sulfonyl]isoindoline (1025424-06-9) → 5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1)

Guidance literature:

With hydrogen bromide; phenol; In propan-1-ol; water; at 100 ℃; for 2h;

upstream raw materials:

N-benzylisoindolin-5-yl methyl ether

4-methoxyphthalimide

5-methoxy-2-[(4-methylphenyl)sulfonyl]isoindoline

3,4-dimethylanisole

Downstream raw materials:

6-methoxy-2-methylisoindolin-5-amine

4-bromophenyl 5-methoxyisoindoline-2-carboxylate

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 5-methoxyisoindoline-2-carboxylate

C₂₀H₂₀F₃NO₅S

Refernces

• 1、 Woodhead, Andrew J.,Angove, Hayley,Carr, Maria G.,Chessari, Gianni,Congreve, Miles,Coyle, Joseph E.,Cosme, Jose,Graham, Brent,Day, Philip J.,Downham, Robert,Fazal, Lynsey,Feltell, Ruth,Figueroa, Eva,Frederickson, Martyn,Lewis, Jonathan,McMenamin, Rachel,Murray, Christopher W.,O'Brien, M. Alistair,Parra, Lina,Patel, Sahil,Phillips, Theresa,Rees, David C.,Rich, Sharna,Smith, Donna-Michelle,Trewartha, Gary,Vinkovic, Mladen,Williams, Brian,Woolford, Alison J.-A.. "Discovery of (2,4-Dihydroxy-5-isopropylphenyl)-[5-(4-methylpiperazin-1- ylmethyl)-1,3-dihydroisoindol-2-yl]methanone (AT13387), a novel inhibitor of the molecular chaperone Hsp90 by fragment based drug design". supporting information; experimental part. p. 5956 - 5969. Retrieved 2010/11/04.
• 2、 -. "ISOINDOLE DERIVATIVES". Page/Page column 22; 23-24. . Retrieved 2010/11/30.