Benzene, 1,4-bis(phthalimidomethyl)-

Base Information

• Chemical Name: Benzene, 1,4-bis(phthalimidomethyl)-
• CAS No.: 30391-55-0
• Molecular Formula: C24H16 N2 O4
• Molecular Weight: 396.402
• NSC Number: 137869
• DSSTox Substance ID: DTXSID80300616
• Wikidata: Q82043826
• Mol file: 30391-55-0.mol

Synonyms:Benzene, 1,4-bis(phthalimidomethyl)-;30391-55-0;2,2'-(1,4-Phenylenebis(methylene))bis(isoindoline-1,3-dione);NSC137869;DTXSID80300616;LXIIWCDTGITVSG-UHFFFAOYSA-N;AKOS024429745;NSC-137869;2-({4-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]phenyl}methyl)-2,3-dihydro-1H-isoindole-1,3-dione;2-(4-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzyl)-1H-isoindole-1,3(2H)-dione #;2-{4-[(1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)METHYL]BENZYL}-1H-ISOINDOLE-1,3(2H)-DIONE

Chemical Property of Benzene, 1,4-bis(phthalimidomethyl)-

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 396.11100700
• Heavy Atom Count: 30
• Complexity: 632

Purity/Quality:

99% ^*data from raw 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)CC3=CC=C(C=C3)CN4C(=O)C5=CC=CC=C5C4=O

Technology Process of Benzene, 1,4-bis(phthalimidomethyl)-

There total 2 articles about Benzene, 1,4-bis(phthalimidomethyl)- 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: 75.0%

phthalimide (136918-14-4,85-41-6) + p-Xylylene dichloride (623-25-6) → 2-(4-chloromethyl-benzyl)-isoindole-1,3-dione (61895-53-2) + α,α-4-bis(1H-isoindol-1,3(2H)-dione)xylene (30391-55-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/ardp.201300011

Reference yield: 32.0%

1,4-bis(bromomethyl)benzene (623-24-5) + phthalimide (136918-14-4,85-41-6) → α,α-4-bis(1H-isoindol-1,3(2H)-dione)xylene (30391-55-0) + 2-{[4-(bromomethyl)phenyl]methyl}-1H-isoindole-1,3(2H)-dione (101367-16-2)

Guidance literature:

phthalimide; With potassium carbonate; for 1h; Milling;

1,4-bis(bromomethyl)benzene; In N,N-dimethyl-formamide; for 1h; regioselective reaction; Milling;

DOI:10.3762/bjoc.13.169

Reference yield: 85.0%

α,α-4-bis(1H-isoindol-1,3(2H)-dione)xylene (30391-55-0) → 2,3-dihydrophthalazine-1,4-dione (1445-69-8) + 1,4-bis(aminomethyl)benzene dihydrochloride (51964-30-8,3057-45-2,116599-23-6)

Guidance literature:

With hydrogenchloride; hydrazine hydrate; In ethanol; 1.) 6 h, reflux, 2.) R_.T_. overnight, 3.) 60 degC, 15 min.;

DOI:10.1139/v82-111

upstream raw materials:

phthalimide

p-Xylylene dichloride

1,4-bis(bromomethyl)benzene

Downstream raw materials:

2,3-dihydrophthalazine-1,4-dione

1,4-bis(aminomethyl)benzene dihydrochloride