2-Butyne-1,4-diol
[CAS# 110-65-6]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives >> Acyclic alcohol
• Name: 2-Butyne-1,4-diol
• Synonyms: 1,4-Dihydroxy-2-butyne; BOZ
• Molecular Formula: C₄H₆O₂
• Molecular Weight: 86.09
• CAS Registry Number: 110-65-6
• EC Number: 203-788-6
• SMILES: C(C#CCO)O

Properties

• Water solubility: 3740 g/L (20 °C)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 53-58 °C (Expl.)
• Index of Refraction: 1.506, Calc.^*
• Boiling Point: 238.0±8.0 °C (760 mmHg), Calc.^*, 38 °C (Expl.)
• Flash Point: 152.2±0.0 °C, Calc.^*, 152 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS06;GHS05;GHS08 Danger
• Risk Statements: H331-H301-H312-H373-H314-H317
• Safety Statements: P260-P261-P262-P264-P264+P265-P270-P271-P272-P280-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P319-P321-P330-P333+P317-P361+P364-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Skin corrosion	Skin Corr.	1B	H314
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H311
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	2	H330

• Transport Information: UN 2716

Discovery and Applications

2-Butyne-1,4-diol is an organic compound with a distinctive chemical structure, featuring a hydroxyl group at each end of a four-carbon chain and a triple bond between the second and third carbons. This structure gives the compound a high degree of reactivity, particularly in the context of polymerization and the formation of other organic derivatives. Due to these properties, 2-butyne-1,4-diol has found a variety of applications in both industrial and laboratory settings.

The discovery of 2-butyne-1,4-diol is linked to the growing interest in the chemistry of alkynes and their ability to undergo diverse reactions. Early synthetic efforts focused on producing linear diols and exploring their reactivity with other organic compounds. The introduction of the alkyne group into the diol framework opened new avenues for the development of materials with specialized properties. Its synthesis can be achieved through various routes, including the reduction of 2-butyne-1,4-dione or through the hydrolysis of intermediate compounds.

One of the primary applications of 2-butyne-1,4-diol is as a monomer in the production of specialized polymers. The compound's dual hydroxyl groups make it an ideal candidate for cross-linking and polymerization reactions, particularly in the formation of polyurethanes and polyesters. When reacted with diisocyanates or other appropriate reagents, 2-butyne-1,4-diol can lead to the synthesis of polymers with enhanced mechanical properties, such as increased tensile strength and durability. These polymers are used in a variety of fields, including the manufacture of coatings, adhesives, and foams.

In addition to its use in polymer chemistry, 2-butyne-1,4-diol serves as an important building block for the synthesis of other organic compounds. Its ability to undergo further functionalization at the hydroxyl groups makes it a versatile intermediate in organic synthesis. One of its key applications is in the preparation of alkynylated derivatives, which can be used as reagents in cross-coupling reactions and other synthetic pathways. These derivatives are important in the production of pharmaceuticals, agrochemicals, and other fine chemicals.

Furthermore, 2-butyne-1,4-diol has found use in the development of materials with specific thermal and chemical resistance. When incorporated into the synthesis of certain polymers, it imparts enhanced stability and resistance to environmental factors such as heat and moisture. This makes it valuable in applications where long-term durability and performance are essential, such as in the production of automotive parts, construction materials, and industrial coatings.

The compound also has applications in the field of analytical chemistry. Its ability to undergo selective reactions with various reagents makes it useful in the development of sensors and detection systems. For example, 2-butyne-1,4-diol can be used as a functional group in the design of chemical sensors for detecting metal ions or other analytes. Its reactivity with different functional groups allows for the creation of selective, sensitive detection systems, which have applications in environmental monitoring and quality control.

In conclusion, 2-butyne-1,4-diol is a versatile compound with a wide range of applications in polymer chemistry, organic synthesis, and materials science. Its reactivity, particularly at the hydroxyl groups and alkyne site, makes it an important building block for the development of functional materials and fine chemicals. Its use in cross-linking, polymerization, and the synthesis of specialized organic compounds continues to make it a valuable tool in both industrial and laboratory settings.

References

1960. Raman-spectrum investigation of 2-butyne-1,4-diol 2-butyne-1,4-diol diacetate, and 1,4-dichloro-2-butyne. Bulletin of the Academy of Sciences of the USSR, Division of chemical science.
DOI: 10.1007/bf00912279

2020. A Schiff Base Modified Pd Catalyst for Selective Hydrogenation of 2-Butyne-1,4-diol to 2-Butene-1,4-diol. Catalysis Letters.
DOI: 10.1007/s10562-020-03125-y

2023. Poly(ether)s derived from oxa-Michael polymerization: a comprehensive review. Monatshefte für Chemie - Chemical Monthly.
DOI: 10.1007/s00706-023-03049-4