2,5-Dioxopyrrolidin-1-yl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-yl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate
• CAS No.: 139346-57-9
• Molecular Formula: C18H18 N2 O6
• Molecular Weight: 358.351
• Hs Code.: 2934999090
• European Community (EC) Number: 674-933-2
• DSSTox Substance ID: DTXSID90375219
• Nikkaji Number: J831.307E
• Wikidata: Q82163746
• Mol file: 139346-57-9.mol

Synonyms:139346-57-9;2,5-Dioxopyrrolidin-1-yl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate;7-(Diethylamino)coumarin-3-carboxylic acid N-succinimidyl ester;deac, se;Succinimidyl 7-Diethylaminocoumarin-3-carboxylate;(2,5-dioxopyrrolidin-1-yl) 7-(diethylamino)-2-oxochromene-3-carboxylate;2H-1-Benzopyran-3-carboxylic acid, 7-(diethylamino)-2-oxo-, 2,5-dioxo-1-pyrrolidinyl ester;N-Succinimidyl 7-(diethylamino)coumarin-3-carboxylate;7-Diethylaminocoumarin-3-carboxylic acid N-succinimidyl ester;7-(Diethylamino)coumarin-3-carboxylic acidN-succinimidyl ester;DEAC,SE;SCHEMBL592979;DTXSID90375219;NUNPVRICKDZFLK-UHFFFAOYSA-N;HY-D0068;MFCD00467585;AKOS015910293;AS-74394;BP-27946;CS-0009982;D5799;FT-0621325;D95251;A807526;A1-30660;F05-0019;J-100103;7-(Diethylamino)coumarin-3-carboxylic acid NHS ester;7-(diethylamino )coumarin-3-carboxylic acid succinimidyl ester;2-Oxo-7-(diethylamino)-alpha-chromene-3-carboxylic acid succinimidyl ester;1-{[7-(Diethylamino)-2-oxo-2H-1-benzopyran-3-carbonyl]oxy}pyrrolidine-2,5-dione;2H-1-Benzopyran-3-carboxylicacid,7-(diethylamino)-2-oxo-,2,5-dioxo-1-pyrrolidinyl ester;7-(Diethylamino)coumarin-3-carboxylic acid N-succinimidyl ester, BioReagent, suitable for fluorescence, >=96.0% (HPLC)

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

Chemical Property:

• Vapor Pressure: 1.53E-12mmHg at 25°C
• Boiling Point: 559.3°Cat760mmHg
• PKA: 2.60 ± 0.20, most basic, temperature: 25 °C
• Flash Point: 292.1°C
• PSA: 97.13000
• Density: 1.4g/cm³
• LogP: 1.79790
• Storage Temp.: −20°C
• Solubility.: DMF: soluble
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 358.11648630
• Heavy Atom Count: 26
• Complexity: 638

Purity/Quality:

99% ^*data from raw suppliers

7-(Diethylamino)coumarin-3-carboxylic acid N-succinimidyl ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C1=CC2=C(C=C1)C=C(C(=O)O2)C(=O)ON3C(=O)CCC3=O
• Uses: Derivatives of 7-aminocoumarins are the most extensively utilized labeling reagents for preparing brightly blue fluorescent conjugates of proteins and nucleic acid. The flourescent-labelling better matches the excitation-wavelength of standard blue lasers 7-(Diethylamino)coumarin-3-carboxylic acid N-succinimidyl ester is an amine reactive fluorescent probe.

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

There total 5 articles about 2,5-Dioxopyrrolidin-1-yl 7-(diethylamino)-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: 99.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 7-(diethylamino)coumarin-3-carboxylic acid (50995-74-9) → 7-(N,N-diethylamino)coumarin-3-carboxylic acid succinimidyl ester (139346-57-9)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1039/c1ob05289f

Reference yield: 50.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 7-diethylamino-2-oxo-2H-chromene-3-carboxylic acid chloride (172646-45-6) → 7-(N,N-diethylamino)coumarin-3-carboxylic acid succinimidyl ester (139346-57-9)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1039/c6sc04158b

Reference yield:

4-(Diethylamino)salicylaldehyde (17754-90-4) → 7-(N,N-diethylamino)coumarin-3-carboxylic acid succinimidyl ester (139346-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: piperdinium acetate / ethanol / 2 h / Reflux

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

With piperdinium acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; N,N-dimethyl-formamide; 1: |Knoevenagel Condensation;

DOI:10.1055/s-0035-1560361

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

7-(diethylamino)coumarin-3-carboxylic acid

4-(diethylamino)-2-hydroxybenzoic acid

4-(Diethylamino)salicylaldehyde

Refernces

• 1、 Zhong, Yuanzhi,Zhan, Jie,Xu, Guanghui,Chen, Yumiao,Qin, Qin,Liao, Xu,Ma, Shaodan,Yang, Zhimou,Cai, Yanbin. "Enzyme-Instructed Self-Assembly Enabled Monomer–Excimer Transition to Construct Higher Ordered Luminescent Supramolecular Assembly for Activity-based Bioimaging". . p. 8121 - 8129. Retrieved 2021.
• 2、 Deng, Zhiqin,Lau, Tai-Chu,Liu, Yingying,Wang, Na,Wang, Zhigang,Xu, Zoufeng,Zhu, Guangyu. "A Photocaged, Water-Oxidizing, and Nucleolus-Targeted Pt(IV) Complex with a Distinct Anticancer Mechanism". . p. 7803 - 7812. Retrieved 2020.
• 3、 Gustafson, Tiffany P.,Metzel, Greg A.,Kutateladze, Andrei G.. "Photochemically amplified detection of molecular recognition events: An ultra-sensitive fluorescence turn-off binding assay". . p. 4752 - 4755. Retrieved 2011.
• 4、 -. "Fluorescent probe for detecting hypochlorous acid, and synthesis method and application thereof". Paragraph 0017. . Retrieved 2019/02/13.