Allyl glycidyl ether
[CAS 106-92-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ether
• Name: Allyl glycidyl ether
• Synonyms: Allyl 2,3-epoxypropyl ether; 1-Allyloxy-2,3-epoxypropane
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• CAS Registry Number: 106-92-3
• EC Number: 203-442-4
• SMILES: C=CCOCC1CO1

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*, Density Data source g/mL (Expl.)
• Melting point: -100 °C (Expl.)
• Boiling point: 153.2±15.0 °C 760 mmHg (Calc.)^*, 154 °C (Expl.)
• Flash point: 57.2 °C (Calc.)^*, 57.2 °C (Expl.)
• Solubility: 50 g/L (20 °C) (Expl.)
• Index of refraction: 1.444 (Calc.)^*, 1.433 (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07;GHS08 DangerGHS02
• Risk Statements: H226-H302-H315-H317-H318-H332-H335-H341-H351-H361f-H412
• Safety Statements: P203-P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P303+P361+P353-P304+P340-P305+P354+P338-P317-P318-P319-P321-P330-P332+P317-P333+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Flammable liquids	Flam. Liq.	3	H226
Reproductive toxicity	Repr.	2	H361
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Germ cell mutagenicity	Muta.	2	H341
Carcinogenicity	Carc.	2	H351
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	5	H313
Acute toxicity	Acute Tox.	2	H330
Reproductive toxicity	Repr.	2	H361f

• Transport Information: UN 2219

chemBlink Chemical Story

Allyl glycidyl ether is useful because one small molecule carries two different kinds of reactivity that can be addressed at different times. One end contains an epoxide ring, a strained three-membered cyclic ether that can undergo ring-opening polymerization or react with nucleophiles. The other end contains an allyl double bond, which can survive many epoxide reactions and later serve as a handle for radical or thiol-ene functionalization. This separation of jobs makes the molecule more than a simple reactive diluent.

Polymer chemists have exploited that orthogonality particularly well. In anionic ring-opening polymerization, the epoxide can be opened repeatedly to build a polyether backbone while the pendant allyl groups remain available along the chain. Lee and co-workers demonstrated controlled preparation of poly(allyl glycidyl ether) with molecular masses from roughly 10 to 100 kg/mol and relatively narrow dispersities. Careful temperature control also suppressed unwanted allyl-to-propenyl isomerization, showing how reaction conditions can preserve the second functional group for later chemistry.

The surviving allyl groups turn the polymer into a modular platform. Thiol-ene reactions can add sulfur-containing molecules across the carbon-carbon double bond under radical conditions. Because many thiols are commercially available or easily synthesized, the same starting polyether can be decorated with hydroxyl, carboxyl, amino, peptide, fluorescent, or other functional groups without rebuilding the main chain. This is an example of post-polymerization modification: first make a well-defined polymer, then decide what chemical personality it should have.

A related strategy uses allyl glycidyl ether as a comonomer with ethylene oxide. The resulting PEG-like copolymers retain the water solubility and biocompatibility associated with poly(ethylene glycol) while providing regularly distributed allyl sites for conjugation. Obermeier and Frey used this concept to create a PEG-based platform for multiple bioconjugation reactions. Instead of attaching one reactive end group to PEG, allyl glycidyl ether can introduce many addressable sites along the chain.

In thermosetting resins and coatings, the same dual functionality gives other possibilities. The epoxide can participate in cure chemistry, while the allyl group can enter radical crosslinking or subsequent modification. Such versatility also means storage and processing conditions matter: unwanted polymerization, epoxide opening, or oxidation must be controlled.

The memorable idea is orthogonality. Allyl glycidyl ether carries two chemical 'ports' that do not have to be used at once. One can construct the polymer backbone and the other can remain dormant until a later step. Modern materials chemistry repeatedly relies on this principle because it separates synthesis from function, allowing one well-controlled scaffold to become many different materials.

References:
1. Lee B.F. et al. Poly(allyl glycidyl ether)-A versatile and functional polyether platform. Journal of Polymer Science Part A. 2011, 49, 4498-4504. DOI: 10.1002/pola.24891.
2. Obermeier B., Frey H. Poly(ethylene glycol-co-allyl glycidyl ether)s: A PEG-based modular synthetic platform for multiple bioconjugation. Bioconjugate Chemistry. 2011, 22, 436-444. DOI: 10.1021/bc1004747.
3. Macromolecules. 2007, functional polyether chemistry involving allyl glycidyl ether. DOI: 10.1021/ma0627875.
4. PubChem. Allyl glycidyl ether, CAS 106-92-3.

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