1,4-Dioxo-3,6-bis(4-bromophenyl)-1,2,4,5-tetrahydropyrrolo[3,4-c]pyrrole-2,5-dicarboxylic acid di-tert-butyl ester

Base Information

• Chemical Name: 1,4-Dioxo-3,6-bis(4-bromophenyl)-1,2,4,5-tetrahydropyrrolo[3,4-c]pyrrole-2,5-dicarboxylic acid di-tert-butyl ester
• CAS No.: 1383674-30-3
• Molecular Formula: C₂₈H₂₆Br₂N₂O₆
• Molecular Weight: 646.332
• Nikkaji Number: J3.104.015I
• Mol file: 1383674-30-3.mol

Synonyms:1383674-30-3;1,4-Dioxo-3,6-bis(4-bromophenyl)-1,2,4,5-tetrahydropyrrolo[3,4-c]pyrrole-2,5-dicarboxylic acid di-tert-butyl ester;Di-tert-butyl 3,6-bis(4-bromophenyl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate;Di-tert-butyl-3,6-bis(4-bromophenyl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate;Di-tert-butyl3,6-bis(4-bromophenyl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate

Chemical Property of 1,4-Dioxo-3,6-bis(4-bromophenyl)-1,2,4,5-tetrahydropyrrolo[3,4-c]pyrrole-2,5-dicarboxylic acid di-tert-butyl ester

Chemical Property:

• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 646.01371
• Heavy Atom Count: 38
• Complexity: 998

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C(=C2C(=C(N(C2=O)C(=O)OC(C)(C)C)C3=CC=C(C=C3)Br)C1=O)C4=CC=C(C=C4)Br

Technology Process of 1,4-Dioxo-3,6-bis(4-bromophenyl)-1,2,4,5-tetrahydropyrrolo[3,4-c]pyrrole-2,5-dicarboxylic acid di-tert-butyl ester

There total 2 articles about 1,4-Dioxo-3,6-bis(4-bromophenyl)-1,2,4,5-tetrahydropyrrolo[3,4-c]pyrrole-2,5-dicarboxylic acid di-tert-butyl ester 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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + 3,6-bis(4-bromophenyl)-2,5-dihydropyrrolo[3, 4-c]pyrrole-1,4-dione (84632-54-2) → di-tert-butyl 3,6-bis(4-bromophenyl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate (1383674-30-3)

Guidance literature:

3,6-bis(4-bromophenyl)-2,5-dihydropyrrolo[3, 4-c]pyrrole-1,4-dione; With dmap; In tetrahydrofuran; at 20 ℃; for 0.25h; Inert atmosphere;

di-tert-butyl dicarbonate; In tetrahydrofuran; at 35 - 45 ℃; Inert atmosphere;

DOI:10.1016/j.dyepig.2012.11.011

Reference yield:

4-bromobenzenecarbonitrile (623-00-7) → di-tert-butyl 3,6-bis(4-bromophenyl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate (1383674-30-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium; iron(III) chloride / tert-Amyl alcohol / 2 h / 120 °C

2: dmap / tetrahydrofuran / 24 h / 20 °C / Schlenk technique; Inert atmosphere

With dmap; iron(III) chloride; sodium; In tetrahydrofuran; tert-Amyl alcohol; 1: |Stobbe Condensation;

DOI:10.1016/j.molstruc.2019.06.022

Reference yield: 99.0%

di-tert-butyl 3,6-bis(4-bromophenyl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate (1383674-30-3) + 4-(dimethylamino)benzene-boronic acid (28611-39-4) → di-tert-butyl 3,6-bis(4'-(dimethylamino)biphenyl-4-yl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate (1416735-48-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In toluene; at 90 ℃; Inert atmosphere;

DOI:10.1016/j.dyepig.2012.11.011

upstream raw materials:

di-tert-butyl dicarbonate

3,6-bis(4-bromophenyl)-2,5-dihydropyrrolo[3, 4-c]pyrrole-1,4-dione

4-bromobenzenecarbonitrile

Downstream raw materials:

di-tert-butyl 3,6-bis(4'-(methylsulfonyl)biphenyl-4-yl)-1,4-dioxopyrrolo[3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate

3,6-bis(4'-methoxybiphenyl-4-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

3,6-bis(4'-(dimethylamino)biphenyl-4-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

3,6-bis(4-styrylphenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione