m-PEG2-4-nitrophenyl carbonate

 CAS No.: 105108-59-6  Cat No.: BP-500680 4.5  

m-PEG2-4-nitrophenyl carbonate is a PEG-based activated carbonate linker designed for stepwise PROTAC assembly via nucleophilic substitution. Structurally, it comprises a short polyethylene glycol chain terminating in a carbonate that is pre-activated by a 4-nitrophenyl leaving group, enabling efficient transfer of the carbonate to amine or other nucleophilic handle-bearing partners under standard organic coupling conditions. The resulting linkage provides a stable, modular connection while retaining PEG’s beneficial effects on solubility and reduced nonspecific aggregation, which are commonly important for maintaining productive ternary complex formation in targeted protein degradation workflows. In PROTAC design, this linker functions as a “reactive handle” that allows researchers to conjugate a PEG spacer between a targeting ligand and an E3 ligase-binding module, thereby tuning spatial geometry and flexibility to improve degradation potency and selectivity. Its use supports reproducible synthesis of well-defined conjugates for structure–activity relationship studies and mechanistic evaluation of degradation pathways.

m-PEG2-4-nitrophenyl carbonate

Structure of 105108-59-6

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PROTAC Linker
Molecular Formula
C₁₂H₁₅NO₇
Molecular Weight
285.25

* For research and manufacturing use only. Not for human or clinical use.

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Please store the product under the recommended conditions in the Certificate of Analysis.
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IUPACName
2-(2-methoxyethoxy)ethyl (4-nitrophenyl) carbonate
InChI Key
PEBJXUZWQCMUAO-UHFFFAOYSA-N
InChI
InChI=1S/C12H15NO7/c1-17-6-7-18-8-9-19-12(14)20-11-4-2-10(3-5-11)13(15)16/h2-5H,6-9H2,1H3
SMILES
COCCOCCOC(=O)OC1=CC=C(C=C1)[N+](=O)[O-]
1. Particulate matter in the indoor and outdoor air of a gymnasium and a fronton
Célia Alves, Ana I Calvo, Liliana Marques, Amaya Castro, Teresa Nunes, Esther Coz, Roberto Fraile Environ Sci Pollut Res Int. 2014 Nov;21(21):12390-402.doi: 10.1007/s11356-014-3168-1.Epub 2014 Jun 18.
An indoor/outdoor monitoring programme of PM10 was carried out in two sports venues (a fronton and a gymnasium). Levels always below 50 μg m(-3) were obtained in the fronton and outdoor air. Due to the climbing chalk and the constant process of resuspension, concentrations above 150 μg m(-3) were registered in the gymnasium. The chalk dust contributed to CO3 (2-) concentrations of 32 ± 9.4 μg m(-3) in this sports facility, which represented, on average, 18 % of the PM10 mass. Here, the carbonate levels were 128 times higher than those registered outdoors. Much lower concentrations, around 1 μg m(-3), were measured in the fronton. The chalk dust is also responsible for the high Mg(2+) concentrations in the gym (4.7 ± 0.89 μg m(-3)), unfolding a PM10 mass fraction of 2.7 %. Total carbon accounted for almost 30 % of PM10 in both indoor spaces. Aerosol size distributions were bimodal and revealed a clear dependence on physical activities and characteristics of the sports facilities. The use of climbing chalk in the gymnasium contributed significantly to the coarse mode. The average geometric mean diameter, geometric standard deviation and total number of coarse particles were 0.77 μm, 2.79 cm(-3) and 28 cm(-3), respectively.
2. Removal of atmospheric CO2 by engineered soils in infrastructure projects
M Ehsan Jorat, Karl E Kraavi, David A C Manning J Environ Manage. 2022 Jul 15;314:115016.doi: 10.1016/j.jenvman.2022.115016.Epub 2022 Apr 20.
The use of crushed basic igneous rock and crushed concrete for enhanced rock weathering and to facilitate pedogenic carbonate precipitation provides a promising method of carbon sequestration. However, many of the controls on precipitation and subsequent effects on soil properties remain poorly understood. In this study, engineered soil plots, with different ratios of concrete or dolerite combined with sand, have been used to investigate relationships between sequestered inorganic carbon and geotechnical properties, over a two-year period. Cone penetration tests with porewater pressure measurements (CPTu) were conducted to determine changes in tip resistance and pore pressure. C and O isotope analysis was carried out to confirm the pedogenic origin of carbonate minerals. TIC analysis shows greater precipitation of pedogenic carbonate in plots containing concrete than those with dolerite, with the highest sequestration values of plots containing each material being equivalent to 33.7 t C ha-1 yr-1 and 17.5 t C ha-1 yr-1, respectively, calculated from extrapolation of results derived from the TIC analysis. TIC content showed reduction or remained unchanged for the top 0.1 m of soil; at a depth of 0.2 m however, for dolerite plots, a pattern of seasonal accumulation and loss of TIC emerged. CPTu tip resistance measurements showed that the presence of carbonates had no observable effect on penetration resistance, and in the case of porewater pressure measurements, carbonate precipitation does not change the permeability of the substrate, and so does not affect drainage. The results of this study indicate that both the addition of dolerite and concrete serve to enhance CO2 removal in soils, that soil temperature appears to be a control on TIC precipitation, and that mineral carbonation in constructed soils does not lead to reduced drainage or an increased risk of flooding.

This m-PEG2-4-nitrophenyl carbonate is a PEG-based PROTAC linker component designed to enable efficient conjugation between targeting ligands and reactive handles. Its carbonate functionality supports controlled linker installation, while the aryl leaving group facilitates nucleophilic substitution under PROTAC-relevant coupling workflows. The PEG spacer can improve solubility and tune the effective distance between binding elements, supporting robust targeted protein degradation strategies. The following sections describe the structure and practical reactivity considerations in detail below.

Structure: The linker contains a PEG ether segment connected through a carbonate linkage to a meta-substituted aromatic ring bearing a nitro group. It features an O-alkyl ether chain, a carbonate C–O framework, and an activated aryl leaving group. These elements collectively provide flexibility and favorable hydrophilicity for PROTAC assembly.

Reactivity: The carbonate can undergo nucleophilic acyl substitution, where nucleophiles such as amines or other suitable oxygen/nitrogen nucleophiles displace the nitrophenyl leaving group to form a new carbonate or related acylated linkage. Coupling is typically performed under anhydrous or low-water conditions using compatible bases to promote nucleophile generation, with polar aprotic solvents commonly employed to maintain solubility and reaction control. Reaction progress is monitored by standard analytical methods, and purification is used to remove unreacted linker and byproducts.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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