1,4-Bis(2-hydroxyethoxy)-2-butyne
[CAS# 1606-85-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Alkyne
• Name: 1,4-Bis(2-hydroxyethoxy)-2-butyne
• Synonyms: 2,2'-[2-Butyne-1,4-diylbis(oxy)]bisethanol; Butynediol ethoxylate; BEO
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.20
• CAS Registry Number: 1606-85-5
• EC Number: 216-526-0
• SMILES: C(COCC#CCOCCO)O

Properties

• Density: 1.144
• Refractive index: 1.485
• Flash point: 180 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

1,4-Bis(2-hydroxyethoxy)-2-butyne is a chemical compound featuring both alkyne and ether groups, as well as two terminal hydroxyl groups. This bifunctional molecule has gained significant attention due to its ability to participate in various chemical reactions and its application in polymer and materials science. The compound was initially synthesized as part of efforts to develop versatile intermediates for polymer modification and crosslinking.

The presence of the alkyne group in 1,4-Bis(2-hydroxyethoxy)-2-butyne provides reactivity that can be exploited in addition and cycloaddition reactions. This characteristic is particularly useful in the synthesis of advanced polymer networks through processes such as click chemistry, where alkyne-azide cycloadditions result in the formation of stable triazole linkages. These reactions have been widely employed to create crosslinked polymeric materials with enhanced thermal stability, mechanical strength, and durability.

The two hydroxyl groups located at each end of the molecule enable it to act as a diol, which can undergo esterification or etherification, making it a valuable building block in the production of polyesters, polyurethanes, and other polymeric materials. The diol functionality also allows for its use as a monomer in the synthesis of block copolymers, which have applications in coatings, adhesives, and elastomers.

One of the most important applications of 1,4-Bis(2-hydroxyethoxy)-2-butyne is in the development of crosslinkable polymers and thermosetting materials. By incorporating this compound into polymer chains, crosslinking can be initiated through reactions at the alkyne site, leading to the formation of highly branched and durable materials. These materials are useful in the creation of coatings, sealants, and other products requiring resistance to environmental degradation and mechanical stress.

In addition, 1,4-Bis(2-hydroxyethoxy)-2-butyne has potential biomedical applications. Its ability to participate in controlled polymerization processes makes it an attractive candidate for developing hydrogels and other biocompatible materials used in drug delivery systems and tissue engineering. The compound's bifunctional nature enables the design of materials with well-defined architectures, crucial for ensuring biocompatibility and controlled degradation in biological environments.

References

2020. Efficient Preparation of Nanoparticle-Reinforced Nickel-based Composite Coating with Highly Preferred (220) Orientation. Chinese Journal of Mechanical Engineering, 33(1), 88.
DOI: 10.1186/s10033-020-00506-7