CAS 126422-58-0

4,7,10,13-tetraoxahexadeca-1,15-diyne

CAS: 126422-58-0 Routes: 3 References: 60

Other Click Chemistry Reagents

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.

Related Reactions: Thiol-Ene · Click-to-Release · Staudinger Ligation

Molecular FormulaC12H18O4 Molecular Weight226.273 g/mol InChIKeyPHRQSGRBGBTBAD-UHFFFAOYSA-N CAS Registry126422-58-0 Literature Refs60 references

Synthesis Routes

Showing 3 of 3 available routes, sorted by yield.

Route 1

1 step Yield: 96%

propargyl bromide
CAS 106-96-7
C3H3Br

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
CAS 112-27-6
C6H14O4

→

4,7,10,13-tetraoxahexadeca-1,15-diyne

Conditions Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium hydride In tetrahydrofuran; mineral oi

Reference Location in patent: experimental part Feng, Yahui; Li, Jingning; Jiang, Lasheng; Gao, Zhihong; Huang, Weicong; Jiang, Fei; Luo, Nianhua; Han, Shujuan; Zeng, Ronghua; Yang, Dingqiao [European Journal of Organic Chemistry, 2011, # 3, p. 562 - 568] DOI

Source Reaxys

Route 2

1 step Yield: 42%

formaldehyd
CH2O

4,7,10,13-tetraoxahexadeca-1,15-diyne
CAS 126422-58-0
C12H18O4

→

4,7,10,13-tetraoxahexadeca-1,15-diyne

Conditions Stage #1: α,ω-bis(O-propargyl)triethylene glycol With n-butyllithium; N,N,N,N,-tetramethylethylenedi

Reference Dabral, Saumya; Bayarmagnai, Bilguun; Hermsen, Marko; Schießl, Jasmin; Mormul, Verena; Hashmi, A. Stephen K.; Schaub, Thomas [Organic Letters, 2019, vol. 21, # 5, p. 1422 - 1425] DOI

Source Reaxys

Route 3

1 step Yield: 37%

1,8-diazido-3,6-dioxaoctane
CAS 59559-06-7
C6H12N6O2

4,7,10,13-tetraoxahexadeca-1,15-diyne
CAS 126422-58-0
C12H18O4

→

4,7,10,13-tetraoxahexadeca-1,15-diyne

Conditions With copper(l) iodide; N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃;

Reference Romanski, Jaroslaw; Stefaniak, Monika [Phosphorus, Sulfur and Silicon and the Related Elements, 2013, vol. 188, # 4, p. 496 - 498] DOI

Source Reaxys

Related Compounds

Other Other Click Chemistry Reagents in our catalog:

tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

CAS 112888-76-3

C14H17NO2 · 37 routes

dibenzazepine glutarylamino tetraethylene glycol acetyl pipecolate methyl ester

CAS 1207355-31-4

C20H17NO3 · 12 routes

(1R,8S,9S)-bicyclo[6.1.0]non-4-yn-9-ylmethyl (4-nitrophenyl) carbonate

CAS 1263166-90-0

C10H14O · 3 routes

2,5-dioxopyrrolidin-1-yl pent-4-ynoate

C32H40N2O8 · 3 routes

DIBAC-biotin

CAS 1418217-95-4

C28H30N4O3S · 3 routes

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