74654-07-2

Basic information

• Product Name: 2-[2-(2-methoxyethoxy)ethoxy]ethylamine
• Synonyms: 2-[2-(2-methoxyethoxy)ethoxy]ethylamine;2-[2-(2-Methoxyethoxy)ethoxy]ethanamine;3,6,9-Trioxadecane-1-amine;2,5,8-trioxatridecane-10-aMine;MPEG3-NH2;EthanaMine,2-[2-(2-Methoxyethoxy)ethoxy]-;3,6,9-Trioxa-1-aminodecane;Methyl-PEG3-amine
• CAS NO: 74654-07-2
• Molecular Formula: C₇H₁₇NO₃
• Molecular Weight: 163.21478
• EINECS: 277-952-0
• Product Categories: MeO-PEG-NH2
• Mol File: 74654-07-2.mol
• Article Data: 44

Chemical Properties

• Boiling Point: 106℃ (11 Torr)
• Flash Point: 86.1°C
• Appearance: /
• Density: 0.978g/cm³
• Vapor Pressure: 0.0939mmHg at 25°C
• Refractive Index: 1.4395 (589.3 nm 20℃)
• Storage Temp.: 2-8°C
• Solubility: Soluble in Water, DMSO, DCM, DMF
• PKA: 8.74±0.10(Predicted)
• CAS DataBase Reference: 2-[2-(2-methoxyethoxy)ethoxy]ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-(2-methoxyethoxy)ethoxy]ethylamine(74654-07-2)
• EPA Substance Registry System: 2-[2-(2-methoxyethoxy)ethoxy]ethylamine(74654-07-2)

Safety Data

• Hazardous Substances Data: 74654-07-2(Hazardous Substances Data)

Usage

Description

2-[2-(2-methoxyethoxy)ethoxy]ethylamine, also known as m-PEG3-amine, is a PEG reagent that contains an amino group (NH2). This amino group is reactive with various functional groups such as carboxylic acids, activated NHS esters, and carbonyls (ketone, aldehyde). The hydrophilic PEG spacer in its structure enhances solubility in aqueous media, making it a versatile compound for various applications.

Uses

Used in Chemical Synthesis:
2-[2-(2-methoxyethoxy)ethoxy]ethylamine is used as a PEG reagent for the synthesis of a variety of molecules, including a series of PROTAC (Proteolysis Targeting Chimeras) molecules. These molecules are designed to induce the degradation of specific proteins, which can be beneficial in the development of targeted therapies for various diseases.
Used in Drug Development:
In the pharmaceutical industry, 2-[2-(2-methoxyethoxy)ethoxy]ethylamine is used as a building block for the synthesis of antibody drug conjugates (ADCs). ADCs are a type of cancer therapy that combines the targeting ability of antibodies with the cytotoxic effects of drugs, allowing for more precise and effective treatment of cancer cells.
Used in Enhancing Solubility:
Due to its hydrophilic PEG spacer, 2-[2-(2-methoxyethoxy)ethoxy]ethylamine is used to improve the solubility of various compounds in aqueous media. This property is particularly useful in the development of new drugs and the formulation of existing ones, as it can help to overcome solubility-related challenges and improve the bioavailability of therapeutic agents.
Used in Polymer Science:
In the field of polymer science, 2-[2-(2-methoxyethoxy)ethoxy]ethylamine can be utilized as a component in the synthesis of polymers with specific properties. The reactive amino group and hydrophilic PEG spacer can be incorporated into polymer structures to tailor their characteristics for various applications, such as drug delivery systems, hydrogels, and coatings.

Synthesis

2-[2-(2-methoxyethoxy)ethoxy]ethylamine is an organic intermediate, which can be prepared from triethylene glycol monomethyl ether as raw material to prepare 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate, and then Reaction with sodium azide,and then Reacts with sodium azide to finally yield 3,6,9-trioxa-1-aminodecane.

InChI:InChI=1/C7H17NO3/c1-9-4-5-11-7-6-10-3-2-8/h2-8H2,1H3

Upstream product

• 52995-76-3 1-chloro-3,6,9-trioxadecane 
• 74654-06-1 2-(2-(2-methoxyethoxy)ethoxy)ethyl azide 
• 167221-50-3 N-[2-(2-(2-methoxyethoxy)ethoxy)ethyl]phthalimide 
• 112-35-6 triethylene glucol monomethyl ether 
• 62921-74-8 2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate 
• 74654-05-0 8-methoxy-1-(methylsulfonyl)oxy-3,6-dioxaoctane 
• 136918-14-4 phthalimide 
• 62921-75-9 2-(2-(2-ethoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate 

Downstream Products

• 70384-57-5 tris-(3,6,9-trioxadecyl)-amine 
• 591230-81-8 5-benzyloxy-isophthalic acid bis-[2-(7-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl)-ethyl] ester 
• 854601-58-4 CH₃(OCH₂CH₂)3-NH-13-cis-retinamide 
• 331273-60-0 (SP-5-13)-([tetrakis[2-[2-(2-methoxyethoxy)ethoxy]ethyl] 4,4',4'',4'''-[10-(3-[[6-(1H-imidazol-1-yl)hexyl]oxy]-4-methylphenyl)-21H,23H-porphine-1,15-diylbis(benzene-2,1,3-triyldioxy)]tetrakis[butanamido]]^(2-)-N⁽²¹⁾,N⁽²²⁾,N⁽²³⁾,N⁽²⁴⁾, N⁽³⁾)zinc(II) 
• 253604-44-3 (SP-4-2)-([tetrakis[2-[2-(2-methoxyethoxy)ethoxy]ethyl] 4,4',4'',4'''-[10-(3,5-bis[[6-(1H-imidazol-1-yl)hexyl]oxy]-4-methylphenyl)-21H,23H-porphine-1,15-diylbis(benzene-2,1,3-triyldioxy)]tetrakis[butanamido]]^(2-)-N⁽²¹⁾,N⁽²²⁾,N⁽²³⁾,N⁽²⁴⁾)zinc(II) 
• 1059587-93-7 mPEG₃-NH-diphenhydramine 
• 1059588-35-0 mPEG₃-N-(diphenhydramine)2 
• 1067915-48-3 N-{2-[2-(2-methoxyethoxy)-ethoxy]-ethyl}-N',N''-di(tetradecyl)benzene-1,3,5-tricarboxamide 
• 1187214-15-8 N-(4-(7-(2-fluoro-4-nitrophenoxy)thieno[3.2-b]pyridin-2-yl)benzyl)-2-(2-(2-methoxyethoxy)ethoxy)ethanamine 
• 1313731-12-2 N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-4-iodobenzamide 
• 1313731-14-4 C₅₄H₆₃N₃O₁₂ 
• 1342833-83-3 4-((6-(7-(4-(3-cyclopropylureido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)piperazine-1-carboxamide 
• 1579295-29-6 4-iodo-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)benzenesulfonamide 
• 1562520-23-3 2-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-1H-benz[d,e]isoquinoline-1,3(2H)-dione 

Relevant articles and documents

Non-invasive, real-time reporting drug release in vitro and in vivo

We developed a real-time drug-reporting conjugate (CPT-SS-CyN) composed of a near-infrared (NIR) fluorescent cyanine-amine dye (CyN), a disulfide linker, and a model therapeutic drug (camptothecin, CPT). Treatment with dithiothreitol (DTT) induces cleavage of the disulfide bond, followed by two simultaneous intramolecular cyclization reactions with identical kinetics, one to cleave the urethane linkage to release the NIR dye and the other to cleave the carbonate linkage to release CPT. The released CyN has an emission wavelength (760 nm) that is significantly different from CPT-SS-CyN (820 nm), enabling easy detection and monitoring of drug release. A linear relationship between the NIR fluorescence intensity at 760 nm and the amount of CPT released was observed, substantiating the use of this drug-reporting conjugate to enable precise, real-time, and non-invasive quantitative monitoring of drug release in live cells and semi-quantitative monitoring in live animals. This journal is

MULTI-ELECTRON REDOX-ACTIVE ORGANIC MOLECULES FOR HIGH-ENERGY-DENSITY NONAQUEOUS REDOX FLOW BATTERIES

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Anion Recognition in Water by Charge-Neutral Halogen and Chalcogen Bonding Foldamer Receptors

A novel strategy for the recognition of anions in water using charge-neutral σ-hole halogen and chalcogen bonding acyclic hosts is demonstrated for the first time. Exploiting the intrinsic hydrophobicity of halogen and chalcogen bond donor atoms integrated into a foldamer structural molecular framework containing hydrophilic functionalities, a series of water-soluble receptors was constructed for an anion recognition investigation. Isothermal titration calorimetry (ITC) binding studies with a range of anions revealed the receptors to display very strong and selective binding of large, weakly hydrated anions such as I- and ReO4-. This is achieved through the formation of 2:1 host-guest stoichiometric complex assemblies, resulting in an encapsulated anion stabilized by cooperative, multidentate, convergent σ-hole donors, as shown by molecular dynamics simulations carried out in water. Importantly, the combination of multiple σ-hole-anion interactions and hydrophobic collapse results in I- affinities in water that exceed all known σ-hole receptors, including cationic systems (β2 up to 1.68 × 1011 M-2). Furthermore, the anion binding affinities and selectivity trends of the first example of an all-chalcogen bonding anion receptor in pure water are compared with halogen bonding and hydrogen bonding receptor analogues. These results further advance and establish halogen and chalcogen bond donor functions as new tools for overcoming the challenging goal of anion recognition in pure water.

Cell-Penetrating Dynamic-Covalent Benzopolysulfane Networks

Cyclic oligochalcogenides (COCs) are emerging as promising systems to penetrate cells. Clearly better than and different to the reported diselenolanes and epidithiodiketopiperazines, we introduce the benzopolysulfanes (BPS), which show efficient delivery, insensitivity to inhibitors of endocytosis, and compatibility with substrates as large as proteins. This high activity coincides with high reactivity, selectively toward thiols, exceeding exchange rates of disulfides under tension. The result is a dynamic-covalent network of extreme sulfur species, including cyclic oligomers, from dimers to heptamers, with up to nineteen sulfurs in the ring. Selection from this unfolding adaptive network then yields the reactivities and selectivities needed to access new uptake pathways. Contrary to other COCs, BPS show high retention on thiol affinity columns. The identification of new modes of cell penetration is important because they promise new solutions to challenges in delivery and beyond.