3-Methyl-1(3H)-isobenzofuranone

Base Information

• Chemical Name: 3-Methyl-1(3H)-isobenzofuranone
• CAS No.: 3453-64-3
• Molecular Formula: C9H8 O2
• Molecular Weight: 148.161
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID10875862
• Nikkaji Number: J750.653H
• Mol file: 3453-64-3.mol

Synonyms:3453-64-3;3-methyl-2-benzofuran-1(3H)-one;3-METHYL-1(3H)-ISOBENZOFURANONE;3-methylphthalide;3-methylisobenzofuran-1(3h)-one;3-methyl-3H-2-benzofuran-1-one;3-Methyl-1,3-dihydro-2-benzofuran-1-one;3-Methyl-2-Oxo-1-Benzofuran;SCHEMBL2668143;SCHEMBL12991261;DTXSID10875862;3-methyl-3H-isobenzofuran-1-one;1(3h)-isobenzofuranone,3-methyl-;BCP32467;1(3H)-Isobenzofuranone, 3-methyl-;3-methyl-2-benzofuran-1(3 H)-one;1(3h)-isobenzo[b]furanone,3-methyl-;CS-0223939;E82504;EN300-117127;3-Methyl-2-benzofuran-1(3H)-one;Butylphthalide Impurity 10

Chemical Property of 3-Methyl-1(3H)-isobenzofuranone

Chemical Property:

• Vapor Pressure: 0.00666mmHg at 25°C
• Boiling Point: 270.9°Cat760mmHg
• Flash Point: 107.9°C
• PSA: 26.30000
• Density: 1.175g/cm³
• LogP: 1.91800
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 148.052429494
• Heavy Atom Count: 11
• Complexity: 176

Purity/Quality:

>95% ^*data from raw suppliers

3-methyl-1(3H)-Isobenzofuranone 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2=CC=CC=C2C(=O)O1
• Uses: 3-Methylphthalide is used as a pharmaceutical compound containing butylphthalide and cosolvent for treating ischemic cerebrovascular disease and relieving nerve function impairment after apoplexy.

Technology Process of 3-Methyl-1(3H)-isobenzofuranone

There total 6 articles about 3-Methyl-1(3H)-isobenzofuranone 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: 24.0%

2-acetylbenzaldehyde (24257-93-0) → (S)-3-methylisobenzofuran-1(3H)-one (3413-14-7,3453-64-3,3205-17-2) + (R)-3-methylisobenzofuran-1(3H)-one (3413-14-7) + acetophenone (98-86-2)

Guidance literature:

With (1S,1S',2R,2R')-2,2'-di-tert-butyl-2,3,2',3'-tetrahydro-1H,1H'-[1,1']biisophosphindolyl; silver tetrafluoroborate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In toluene; at 90 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja907711a

Reference yield: 11.0%

2-acetyl-benzoic acid (577-56-0) → 3-methylphthalide (3453-64-3) + 1-(1-hydroxyethyl)-2-hydroxymethylbenzene (57259-71-9) + (2-ethylphenyl)methanol (767-90-8)

Guidance literature:

With samarium diiodide; water; In tetrahydrofuran; for 0.0333333h; Ambient temperature;

DOI:10.1246/cl.1993.1495

Reference yield: 10.0%

2-ethylbenzoic acid (612-19-1) → isochroman-1-one (4702-34-5) + 3-methylphthalide (3453-64-3)

Guidance literature:

With copper dichloride; potassium tetrachloroplatinate; In water; at 150 ℃; for 24h;

DOI:10.1016/j.tetlet.2005.12.104

upstream raw materials:

2-acetyl-benzoic acid

2-ethylbenzoic acid

2-acetylbenzaldehyde

ethyl-benzoic acid methyl ester

Downstream raw materials:

4-aminoethylbenzene

2-ethyl-thiobenzoic acid amide

o-ethylbenzonitrile

2-ethylbenzoic acid

Refernces

• 1、 Holec, Claudia,Hartrampf, Ute,Neufeld, Katharina,Pietruszka, J?rg. "P450 BM3-Catalyzed Regio- and Stereoselective Hydroxylation Aiming at the Synthesis of Phthalides and Isocoumarins". . p. 676 - 684. Retrieved 2017/04/11.
• 2、 Phan, Diem H. T.,Kim, Byoungmoo,Dong, Vy M.. "Phthalides by rhodium-catalyzed ketone hydroacylation". supporting information; experimental part. p. 15608 - 15609. Retrieved 2010/01/30.