1,5-Diamino-3-oxapentane

 CAS No.: 2752-17-2  Cat No.: BP-500289  Purity: 98% 4.5  

1,5-Diamino-3-oxapentane is a bifunctional linker building block featuring two primary amine termini separated by a three-carbon framework containing an ether oxygen. Structurally, it provides a flexible, hydrophilic spacer that can be used to connect or distance reactive handles on PROTAC components, such as an E3-ligase ligand and a target-binding moiety, while maintaining appropriate conformational freedom for productive ternary complex formation. In PROTAC design, linkers must balance length, flexibility, and polarity to promote effective binding geometry and to reduce off-target interactions; diamino-ether spacers like this are commonly employed for amide or urea coupling strategies after suitable functional group activation. Its value for targeted protein degradation research lies in enabling systematic structure–activity relationship studies, where modifying linker composition and spacing can tune degradation potency, cooperativity, and cellular activity.

1,5-Diamino-3-oxapentane

Structure of 2752-17-2

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Category
PROTAC Linker
Molecular Formula
C4H12N2O
Molecular Weight
104.1509
Appearance
Colorless to Almost colorless clear liquid

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

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Purity
98%
Appearance
Colorless to Almost colorless clear liquid
Storage
4°C, protect from light; In solvent, -80°C, 6 months; -20°C, 1 month (protect from light)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-(2-aminoethoxy)ethanamine
Synonyms
2,2'-oxybis-ethanamin; 2,2'-OXYBIS(ETHYLAMINE); 2,2'-OXYDIETHYLAMINE; 2,2'-DIAMINODIETHYL ETHER; 1,5-DIAMINO-3-OXAPENTANE; BIS(2-AMINOETHYL) ETHER; 1,5-DIAMINO-3-OXAPENTANE 98%; 2,2'-Oxybis(ethanamine)
Boiling Point
64 °C/4 mmHg
Density
0.961 g/cm3
InChI Key
GXVUZYLYWKWJIM-UHFFFAOYSA-N
InChI
InChI=1S/C4H12N2O/c5-1-3-7-4-2-6/h1-6H2
SMILES
C(COCCN)N
1. Effectiveness of High-Intensity Interval Training (HIT) and Continuous Endurance Training for VO2max Improvements: A Systematic Review and Meta-Analysis of Controlled Trials
Zoran Milanović, Goran Sporiš, Matthew Weston Sports Med. 2015 Oct;45(10):1469-81.doi: 10.1007/s40279-015-0365-0.
Background:Enhancing cardiovascular fitness can lead to substantial health benefits. High-intensity interval training (HIT) is an efficient way to develop cardiovascular fitness, yet comparisons between this type of training and traditional endurance training are equivocal. Objective:Our objective was to meta-analyse the effects of endurance training and HIT on the maximal oxygen consumption (VO2max) of healthy, young to middle-aged adults.
2. Cataract prevalence and prevention in Europe: a literature review
Elena Prokofyeva, Alfred Wegener, Eberhart Zrenner Acta Ophthalmol. 2013 Aug;91(5):395-405.doi: 10.1111/j.1755-3768.2012.02444.x.Epub 2012 Jun 20.
This literature review is aimed at the evaluation of the potential for cataract prevention in Europe. It was performed using PubMed with Mesh and free-text terms. Studies included were (i) performed on a population of Caucasian origin at an age range of 40-95 years, (ii) cataract was clinically verified, (iii) drug record of prescriptions, their indication, a record of every diagnosis, dosage and quantity of prescribed medicine were available, (iv) sample size >300 and (v) published between 1990 and 2009. The results of 29 articles were reviewed. Former [3.75 (2.26-6.21)] or current smoking [2.34 (1.07-5.15)], diabetes of duration >10 years [2.72 (1.72-4.28)], asthma or chronic bronchitis [2.04 (1.04-3.81)], and cardiovascular disease [1.96 (1.22-3.14)] increased the risk of cataract. Cataract was more common in patients taking chlorpromazine during ≥90 days with a dosage ≥300 mg [8.8 (3.1-25.1)] and corticosteroids >5 years [3.25 (1.39-7.58)] in a daily dose >1600 mg [1.69 (1.17-2.43)]. Intake of a multivitamin/mineral formulation [2.00 (1.35-2.98)] or corticosteroids [2.12 (1.93-2.33)] also increased the risk of cataract. Corticosteroids applied orally [3.25 (1.39-7.58)], parenteral [1.56 (1.34-1.82)] or inhalational [1.58 (1.46-1.71)] lead to cataract more frequently than those applied topically: nasal [1.33 (1.21-1.45)], ear [1.31 (1.19-1.45)] or skin [1.43 (1.36-1.50)]. Outpatient cataract surgery was negatively associated with total cataract surgery costs, and chlorpromazine, corticosteroids and multivitamin/mineral formation increase the risk of posterior subcapsular cataract dependent on dose, treatment application and duration. This review presented a comprehensive overview of specific and general cataract risk factors and an update on most recent experimental studies and randomized control trials directed at cataract prevention.

1,5-Diamino-3-oxapentane, provides a flexible, hydrophilic, diamine-based scaffold suitable for constructing bifunctional degraders. Its ether-containing backbone and primary amine termini enable robust conjugation strategies to assemble ligand–linker–ligand architectures. The resulting linkers can support efficient spatial presentation and tunable geometry in targeted protein degradation workflows. Detailed structural and synthetic considerations are provided below.

Structure: 1,5-Diamino-3-oxapentane is a flexible aliphatic linker featuring a central ether oxygen within a short chain and two primary amine groups at the terminal positions. The molecule contains C–N and C–O single bonds, with basic amine functionality that can form salts and participate in standard amide or carbamate-forming coupling chemistry.

Reactivity: The two primary amines are well suited for nucleophilic acyl substitution and condensation reactions commonly used in PROTAC synthesis. Typical approaches include forming amide bonds via activated carboxylic acids or using carbamate-forming reagents, often under mild base conditions. Appropriate solvents such as polar aprotic media or aqueous-organic mixtures are selected to maintain solubility and minimize side reactions. Reaction planning should consider pH control to preserve amine reactivity and compatibility with functional groups on the targeting ligands.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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Historical Records: 1,5-Diamino-3-oxapentane

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