N-[2-(Dansylamino)ethyl]maleimide

Base Information

• Chemical Name: N-[2-(Dansylamino)ethyl]maleimide
• CAS No.: 160291-45-2
• Molecular Formula: C18H19 N3 O4 S
• Molecular Weight: 373.42616
• Hs Code.: 2935009090
• European Community (EC) Number: 634-927-2
• DSSTox Substance ID: DTXSID00439098
• Nikkaji Number: J613.162J
• Wikidata: Q82254989
• Mol file: 160291-45-2.mol

Synonyms:N-[2-(Dansylamino)ethyl]maleimide;160291-45-2;5-(dimethylamino)-N-[2-(2,5-dioxopyrrol-1-yl)ethyl]naphthalene-1-sulfonamide;5-(Dimethylamino)-N-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)naphthalene-1-sulfonamide;N-(2-Maleimidoethyl)dansylamide;SCHEMBL9894850;DTXSID00439098;N-(2-Maleimidoethyl)-5-dimethylamino-1-naphthalenesulfonamide;AMY22433;AKOS015908562;AS-82553;E79407;N-[2-(Dansylamino)ethyl]maleimide, BioReagent, suitable for fluorescence, >=99.0% (HPLC);1-Naphthalenesulfonamide,N-[2-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethyl]-5-(dimethylamino)-;5-(Dimethylamino)-N-[2-[(2,5-dioxo-2,5-dihydro-1H-pyrrol)-1-yl]ethyl]naphthalene-1-sulfonamide

Chemical Property of N-[2-(Dansylamino)ethyl]maleimide

Chemical Property:

• PSA: 95.17000
• LogP: 2.51870
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 373.10962727
• Heavy Atom Count: 26
• Complexity: 665

Purity/Quality:

N-[2-(Dansylamino)ethyl]maleimide BioReagent, suitable for fluorescence, ≥99.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=CC2=C1C=CC=C2S(=O)(=O)NCCN3C(=O)C=CC3=O

Technology Process of N-[2-(Dansylamino)ethyl]maleimide

There total 8 articles about N-[2-(Dansylamino)ethyl]maleimide 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: 71.0%

2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethanaminium chloride (134272-64-3) + 5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) → 5-(dimethylamino)-N-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)naphthalene-1-sulfonamide (160291-45-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.201912095

Reference yield: 44.4%

N-(2-aminoethyl)maleimide trifluoroacetic acid salt (146474-00-2) + 5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) → 5-(dimethylamino)-N-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)naphthalene-1-sulfonamide (160291-45-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 7h; Inert atmosphere; Darkness;

DOI:10.1039/c9cc07443k

Reference yield:

(Z)-3-[2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-ethylcarbamoyl]-acrylic acid → 5-(dimethylamino)-N-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)naphthalene-1-sulfonamide (160291-45-2)

Guidance literature:

With cobalt naphthenate; acetic anhydride; In N,N-dimethyl acetamide; at 70 - 80 ℃; for 2h; Yield given;

upstream raw materials:

5-(dimethylamino)naphth-1-ylsulfonyl chloride

dansylethylenediamine

tert-butyl 2-(5-(dimethylamino)naphthalene-1-sulfonamido)ethylcarbamate

N-[2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl]-carbamic acid tert-butyl ester