2,5-Dioxopyrrolidin-1-yl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-yl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
• CAS No.: 134471-24-2
• Molecular Formula: C₁₄H₉NO₇
• Molecular Weight: 303.228
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20420706
• Nikkaji Number: J1.902.433D
• Wikidata: Q72483546
• Mol file: 134471-24-2.mol

Synonyms:134471-24-2;2,5-Dioxopyrrolidin-1-yl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate;7-Hydroxycoumarin-3-carboxylic acid N-succinimidyl ester;N-Succinimidyl 7-hydroxycoumarin-3-carboxylate;(2,5-dioxopyrrolidin-1-yl) 7-hydroxy-2-oxochromene-3-carboxylate;C14H9NO7;SCHEMBL591197;Umbelliferone-3-carboxylic acid N-succinimidyl ester;DTXSID20420706;HY-D0115;MFCD00037568;AKOS015908557;AS-72060;N-Succinimidyl Umbelliferone-3-carboxylate;CS-0010025;FT-0621432;Succinimidyl 7-hydroxycoumarin-3-carboxylate;T71729;N-Succinimidyl 7-hydroxycoumarin-3-car-boxylate;A1-06642;F05-0013;J-100178;7-Hydroxycoumarin-3-carboxylic acid succinimidyl ester;7-Hydroxycoumarin-3-carboxylicacid,succinimidyl ester;7-Hydroxycoumarin-3-carboxylic acid, succinimidyl ester;7-HYDROXYCOUMARIN-3-CARBOXYLICACIDN-SUCCINIMIDYLESTER;2-Oxo-7-hydroxy-2H-1-benzopyran-3-carboxylic acid succinimidyl ester;7-Hydroxycoumarin-3-carboxylic acid N-succinimidyl ester, suitable for fluorescence, >=95.0% (coupling assay to aminopropyl silica gel);N-Succinimidyl 7-hydroxycoumarin-3-carboxylate, Umbelliferone-3-carboxylic acid N-succinimidyl ester

Chemical Property of 2,5-Dioxopyrrolidin-1-yl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate

Chemical Property:

• Vapor Pressure: 4.25E-13mmHg at 25°C
• Boiling Point: 558.9oC at 760 mmHg
• PKA: 7.09 ± 0.20, most acidic, temperature: 25 °C
• Flash Point: 291.8oC
• PSA: 114.12000
• Density: 1.68g/cm3
• LogP: 0.65730
• Storage Temp.: −20°C
• Solubility.: DMF: soluble
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 303.03790163
• Heavy Atom Count: 22
• Complexity: 566

Purity/Quality:

98%,99%, ^*data from raw suppliers

7-Hydroxycoumarin-3-carboxylic acid N-succinimidyl ester ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)C2=CC3=C(C=C(C=C3)O)OC2=O
• Uses: 7-Hydroxycoumarin-3-carboxylic acid N-succinimidyl ester is a compound suitable for fluorescence.

Technology Process of 2,5-Dioxopyrrolidin-1-yl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate

There total 4 articles about 2,5-Dioxopyrrolidin-1-yl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate 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: 92.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid (779-27-1) → 2,5-dioxopyrrolidin-1-yl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate (134471-24-2)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1039/c0ob01042a

Reference yield: 86.0%

di(succinimido) carbonate (74124-79-1) + 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid (779-27-1) → 2,5-dioxopyrrolidin-1-yl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate (134471-24-2)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

Reference yield:

7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester (6093-71-6) → 2,5-dioxopyrrolidin-1-yl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate (134471-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; water / Reflux

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C

With hydrogenchloride; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1039/c0ob01042a

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid

7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester

2,4-Dihydroxybenzaldehyde

Downstream raw materials:

C₂₉H₂₆N₂O₅

7-hydroxycoumarin

Refernces

• 1、 Amara, Neri,Foe, Ian T.,Onguka, Ouma,Garland, Megan,Bogyo, Matthew. "Synthetic Fluorogenic Peptides Reveal Dynamic Substrate Specificity of Depalmitoylases". . p. 35 - 7,47. Retrieved 2018/10/24.
• 2、 Yoon, Hyung-Jo,Dakanali, Marianna,Lichlyter, Darcy,Chang, Willy M.,Nguyen, Karen A.,Nipper, Matthew E.,Haidekker, Mark A.,Theodorakis, Emmanuel A.. "Synthesis and evaluation of self-calibrating ratiometric viscosity sensors". supporting information; experimental part. p. 3530 - 3540. Retrieved 2011/06/25.