N-Boc-2-Maleimidoethylamine

Base Information

• Chemical Name: N-Boc-2-Maleimidoethylamine
• CAS No.: 134272-63-2
• Molecular Formula: C₁₁H₁₆N₂O₄
• Molecular Weight: 240.259
• Hs Code.: 2925190090
• DSSTox Substance ID: DTXSID50400314
• Nikkaji Number: J2.672.729D
• Wikidata: Q82203223
• Mol file: 134272-63-2.mol

Synonyms:134272-63-2;N-Boc-2-Maleimidoethylamine;Mal-NH-Boc;tert-Butyl (2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)carbamate;tert-butyl 2-(2,5-dioxo-2H-pyrrol-1(5H)-yl)ethylcarbamate;Tert-butyl N-[2-(2,5-dioxopyrrol-1-yl)ethyl]carbamate;N-(2-Boc-amino)ethyl Maleimide;[2-(2,5-DIOXO-2,5-DIHYDRO-PYRROL-1-YL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER;N-(2-[(t-Boc)amino]ethyl Maleimide;tert-Butyl 2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethylcarbamate;Tert-butyl [2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]carbamate;SCHEMBL998261;AMY574;DTXSID50400314;SNYRFQCLCLMCCG-UHFFFAOYSA-N;MFCD03425523;AS-36886;BP-20992;HY-140991;CS-0115769;FT-0663446;N-[2-(tert-Butoxycarbonylamino)ethyl]maleimide;(2-Maleimido)ethylcarbamic acid tert-butyl ester;2-(maleimido)ethylcarbamic acid tert-butyl ester;A906320;J-006508;N-(2-((tert-Butoxycarbonyl)amino)ethyl)-maleimide;N-[2-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethyl]carbamic Acid 1,1-Dimethylethyl Ester

Chemical Property of N-Boc-2-Maleimidoethylamine

Chemical Property:

• Melting Point: 110-115°C
• Boiling Point: 390.9±25.0 °C(Predicted)
• PKA: 12.09±0.46(Predicted)
• PSA: 75.71000
• Density: 1.210±0.06 g/cm3(Predicted)
• LogP: 0.76490
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 240.11100700
• Heavy Atom Count: 17
• Complexity: 350

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl N-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCN1C(=O)C=CC1=O
• Description: tert-butyl 2-(2,5-dioxo-2H-pyrrol-1(5H)-yl)ethylcarbamate contains a maleimide group and a Boc-protected amine group. The protected amine can be deprotected under acidic conditions. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.
• Uses: N-BOC-2-MALEIMIDOETHYLAMINE is used in the Mitsunobu reaction: a novel method for the synthesis of bifunctional maleimide linkers.

Technology Process of N-Boc-2-Maleimidoethylamine

There total 14 articles about N-Boc-2-Maleimidoethylamine 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: 92.1%

N-methoxycarbonylmaleimide (55750-48-6) + N-BOC-1,2-diaminoethane (57260-73-8) → N-[2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl]-carbamic acid tert-butyl ester (134272-63-2)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃; for 1.5h; Cooling with ice;

DOI:10.1021/bc5004058

Reference yield: 92.0%

N-ethoxycarbonylmaleinimide (55750-49-7) → N-[2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl]-carbamic acid tert-butyl ester (134272-63-2)

Guidance literature:

In tetrahydrofuran; sodium hydrogencarbonate;

Reference yield: 86.0%

maleic anhydride (108-31-6) + N-BOC-1,2-diaminoethane (57260-73-8) → N-[2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl]-carbamic acid tert-butyl ester (134272-63-2)

Guidance literature:

maleic anhydride; N-BOC-1,2-diaminoethane; With triethylamine; In ethanol; at 0 ℃; for 4h; Inert atmosphere;

With sodium acetate; acetic anhydride; In ethanol; at 70 ℃; for 3h; Inert atmosphere;

DOI:10.1002/ejoc.202000093

upstream raw materials:

maleiimide

2-(N-tert-butoxycarbonylamino)ethanol

(Z)-3-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-acrylic acid

N-methoxycarbonylmaleimide

Downstream raw materials:

1-(2-aminoethyl)-1H-pyrrole-2,5-dione

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

1-(2-(D-biotinamido)ethyl)-1H-pyrrole-2,5-dione

5-(dimethylamino)-N-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)naphthalene-1-sulfonamide