CAS 132178-37-1
2,5-dioxopyrrolidin-1-yl pent-4-ynoate
About This Compound
This category encompasses diverse reagents used across various click chemistry reactions, including activated esters, Michael acceptors, epoxides, and multi-functional building blocks. These compounds participate in thiol-ene reactions, Michael additions, ring-opening reactions, and other modular coupling strategies that meet the criteria of click chemistry — high yield, wide scope, simple conditions, and easy purification.
VLQOCPXVAZTWQR-UHFFFAOYSA-N
CAS Registry132178-37-1
Literature Refs378 references
Synthesis Routes
Showing 3 of 9 available routes, sorted by yield.
Route 1
CAS 6066-82-6
C4H5NO3
CAS 6089-09-4
C5H6O2
Route 2
CAS 132178-37-1
C9H9NO4
CAS 1980012-04-1
CH2O2*C24H45N3O7
Route 3
CAS 6089-09-4
C5H6O2
BF4*C9H16N3O3
Related Compounds
Other Other Click Chemistry Reagents in our catalog:
Frequently Asked Questions
What defines a reaction as "click chemistry"?
According to Sharpless (2001), click reactions must be modular, wide in scope, high-yielding, generate only inoffensive byproducts, be stereospecific, and use readily available starting materials. They should proceed under simple conditions (ideally insensitive to oxygen and water), use benign solvents, and products should be easy to isolate without chromatography.
How do I choose the right click reaction for my application?
For in vitro bioconjugation: CuAAC is the gold standard. For live-cell work: use SPAAC or IEDDA (copper-free). For protein labeling: SuFEx or Staudinger ligation. For polymer chemistry: thiol-ene or thiol-Michael. For prodrug activation: click-to-release (IEDDA-based elimination). Consider reaction speed, biocompatibility, and orthogonality requirements.
Can click reactions be performed in aqueous media?
Most click reactions are compatible with aqueous conditions. CuAAC works in water/t-BuOH mixtures. SPAAC and IEDDA proceed rapidly in pure aqueous buffer. Thiol-ene reactions can be performed in water with water-soluble photoinitiators. SuFEx reactions work in organic/aqueous biphasic systems. This aqueous compatibility is one of the key advantages of click chemistry for biological applications.
How do I confirm click reaction completeness?
For CuAAC/SPAAC: disappearance of the azide stretch at ~2100 cm⁻¹ in IR spectroscopy. For IEDDA: loss of the tetrazine UV-Vis absorption (pink color fades). General methods: TLC, HPLC, ¹H NMR (triazole peak), and mass spectrometry. For bioconjugation: SDS-PAGE with fluorescent readout or western blot.
What is the typical shelf life of click chemistry reagents?
Azides: 6–12 months at −20 °C (avoid light). Terminal alkynes: 12+ months at −20 °C. Cyclooctynes (DIBO, DBCO, BCN): 6–12 months at −20 °C (light-sensitive). Tetrazines: 6–12 months at −20 °C (light and moisture sensitive). TCO derivatives: 3–6 months at −20 °C (isomerization-prone). Sulfonyl fluorides: 12+ months at room temperature.
Last updated: July 27, 2026