4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride

Base Information

• Chemical Name: 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride
• CAS No.: 29305-46-2
• Molecular Formula: C11H6ClNO3
• Molecular Weight: 235.627
• DSSTox Substance ID: DTXSID20538375
• Nikkaji Number: J805.282D
• Wikidata: Q82413739
• Mol file: 29305-46-2.mol

Synonyms:29305-46-2;4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride;4-maleimidobenzoyl chloride;Benzoyl chloride, 4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-;Para-maleimidobenzoyl chloride;SCHEMBL398038;DTXSID20538375;BCHKIOWPKLJEKK-UHFFFAOYSA-N;MFCD03421601;AKOS000308546;N-(4-(chlorocarbonyl)phenyl)maleimide

Chemical Property of 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride

Chemical Property:

• PSA: 54.45000
• LogP: 1.56000
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 235.0036207
• Heavy Atom Count: 16
• Complexity: 351

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)Cl)N2C(=O)C=CC2=O

Technology Process of 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride

There total 5 articles about 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride 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: 85.2%

N-(4-carboxyphenyl)maleimide (17057-04-4) → 4-(2,5-dioxo-2,5-dihydro-1-pyrrol-1-yl)benzoyl chloride (29305-46-2)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In benzene; for 2h; Reflux;

DOI:10.1134/S1070428015060159

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-(2,5-dioxo-2,5-dihydro-1-pyrrol-1-yl)benzoyl chloride (29305-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetone / 20 °C

1.2: Mg(OAc)2; Et₃N; Ac₂O / 0.75 h / Heating

2.1: thionyl chloride / benzene / 4 h / 80 °C

With thionyl chloride; In acetone; benzene;

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-(2,5-dioxo-2,5-dihydro-1-pyrrol-1-yl)benzoyl chloride (29305-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / P₂O₅ / dioxane / 18 h / Heating

2: 0.28 g / SOCl₂ / 12 h / Heating

With thionyl chloride; phosphorus pentoxide; In 1,4-dioxane;

DOI:10.1021/ja050339r

upstream raw materials:

N-(4-carboxyphenyl)maleimide

4-amino-benzoic acid

maleic anhydride

Downstream raw materials:

methyl 4‐(2,5‐dioxo‐2,5‐dihydro‐1H‐pyrrol‐1‐yl)benzoate

4-maleimido-benzoic acid-[4-(tetrachlorocyclopentadienylidene-methyl)-phenyl ester]

2,2-bis[4-(4-maleimidobenzoyloxy)phenyl]hexafluoropropane

2,2-bis[4-(4-maleimidobenzoyloxy)phenyl]propane