2-[2-[2-(Boc-amino)ethoxy]ethoxy]acetic Acid DCHA is the dicyclohexylamine (DCHA) salt of Boc-NH-PEG2-CH₂COOH — a Boc-protected, PEG2-spaced amino acid building block. The molecular formula is C₂₃H₄₄N₂O₆ (MW 444.61), and it presents as a white to off-white crystalline powder. The structure combines three functional elements: a tert-butoxycarbonyl (Boc)-protected primary amine, a diethylene glycol (PEG2) spacer, and a terminal acetic acid (–CH₂COOH), paired with one equivalent of dicyclohexylamine (DCHA). Unlike the free acid form, which is often a viscous oil or sticky semi-solid, the DCHA salt is a crystalline, free-flowing powder that is stable, easy to weigh, and convenient to handle on a laboratory scale.
Why the DCHA salt form? Many PEG‑containing building blocks, including 2-[2-[2-(Boc-amino)ethoxy]ethoxy]acetic Acid DCHA as the free acid (CAS 108466‑89‑3), are isolated as waxy or oily materials that are difficult to handle, prone to moisture absorption, and challenging to dispense accurately. Conversion to 2-[2-[2-(Boc-amino)ethoxy]ethoxy]acetic Acid DCHA yields a crystalline white powder with a sharp melting point (114–122 °C) and improved long‑term stability. Upon use, 2-[2-[2-(Boc-amino)ethoxy]ethoxy]acetic Acid DCHA is simply suspended or dissolved in an organic solvent (e.g., DMF, DCM, EtOAc) and the free acid is liberated by washing with dilute aqueous acid (e.g., 5% citric acid or 0.5 M H₂SO₄), or the DCHA can be displaced during amide coupling conditions (HATU/DIPEA). This salt form is particularly valued in Boc‑SPPS (solid‑phase peptide synthesis), where the linker is introduced using standard Boc chemistry protocols. The PEG2 spacer (two ethylene glycol units, approximately 9 atoms linear length) provides a short, hydrophilic bridge that enhances solubility of peptide conjugates, reduces aggregation, and introduces flexibility into molecular constructs. Cosperpharm supplies 2-[2-[2-(Boc-amino)ethoxy]ethoxy]acetic Acid DCHA with high purity (≥97–99% by HPLC/TLC), full documentation, and competitive lead times. It is a versatile building block for peptide synthesis, PROTAC development, ADC linker construction, drug delivery systems, and bioconjugation.
DCHA Salt: What You Need to Know
Dicyclohexylamine is a bulky, lipophilic secondary amine that forms stable crystalline salts with carboxylic acids. In the context of Boc‑NH‑PEG2‑CH₂COOH, the DCHA salt offers several practical advantages:
● Crystalline solid – Melting point 114–122°C, confirming high crystallinity and purity [8†L10-L11].
● Easy handling – Free‑flowing powder that does not stick to spatulas or containers.
● Improved stability – Less prone to moisture absorption and degradation during long‑term storage compared to the free acid.
● Simple conversion to free acid – Dissolve the DCHA salt in an organic solvent (e.g., EtOAc, DCM) and wash with dilute aqueous acid (5% citric acid, 0.5 M H₂SO₄) to extract DCHA into the aqueous phase, leaving the free Boc‑NH‑PEG2‑CH₂COOH in the organic layer.
Alternatively, the DCHA salt can be used directly in amide couplings: the DCHA is displaced during activation with HATU/DIPEA or other coupling reagents, provided sufficient base is present.
Q1: How does this DCHA salt differ from the free acid (CAS 108466‑89‑3)?
A: The free acid (CAS 108466‑89‑3, Boc‑NH‑PEG2‑CH₂COOH, MW 263.29) is typically isolated as a viscous oil or waxy solid that is difficult to handle and prone to degradation. The DCHA salt (CAS 560088‑79‑1, MW 444.61) is a crystalline, free‑flowing powder with a sharp melting point (114–122°C), easy to weigh and store. Upon use, the DCHA is removed by an acidic aqueous wash, or the salt can be used directly in coupling reactions with sufficient base.
Q2: What is the storage class of this compound?
A: This product is classified as Storage Class 11 – Combustible Solids. It should be stored away from open flames and strong oxidizers.
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